J. Larry Campbell,* A,B Amy Meng-Ci Yang, B Luke R. Melo, B W. Scott Hopkins* B

Studying Gas-phase Interconversion of Tautomers using Differential Mobility Spectrometry

J. Larry Campbell,*[a,b] Amy Meng-Ci Yang,[b] Luke R. Melo,[b] W. Scott Hopkins*[b]

Supporting Information

Table of Contents

Figure S1. HDX results for D2O environments

Figure S2. MS/MS results following H2O environment

Figure S3. Lowest Energy N-protonated Structures

N-protonated (4-ABA)•(MeOH)•H+

N-protonated (4-ABA)•(MeOH)2•H+

N-protonated (4-ABA)•(MeOH)3•H+ (Isomer 1)

N-protonated (4-ABA)•(MeOH)3•H+ (Isomer 2)

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 1)

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 2)

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 3)

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 4)

N-protonated (4-ABA)•(MeOH)5•H+ (Isomer 1)

N-protonated (4-ABA)•(MeOH)5•H+ (Isomer 2)

N-protonated (4-ABA)•(MeOH)5•H+ (Isomer 3)

N-protonated (4-ABA)•(MeOH)6•H+ (Isomer 1)

N-protonated (4-ABA)•(MeOH)6•H+ (Isomer 2)

N-protonated (4-ABA)•(MeOH)7•H+ (Isomer 1)

N-protonated (4-ABA)•(MeOH)7•H+ (Isomer 2)

N-protonated (4-ABA)•(MeOH)8•H+ (Isomer 1)

N-protonated (4-ABA)•(MeOH)8•H+ (Isomer 2)

Figure S4. Lowest Energy O-protonated Structures

O-protonated (4-ABA)•(MeOH)•H+

O-protonated (4-ABA)•(MeOH)2•H+

O-protonated (4-ABA)•(MeOH)3•H+ (Isomer 1)

O-protonated (4-ABA)•(MeOH)3•H+ (Isomer 2)

O-protonated (4-ABA)•(MeOH)4•H+ (Isomer 1)

O-protonated (4-ABA)•(MeOH)4•H+ (Isomer 2)

O-protonated (4-ABA)•(MeOH)5•H+ (Isomer 1)

O-protonated (4-ABA)•(MeOH)5•H+ (Isomer 2)

O-protonated (4-ABA)•(MeOH)6•H+ (Isomer 1)

O-protonated (4-ABA)•(MeOH)6•H+ (Isomer 2)

O-protonated (4-ABA)•(MeOH)7•H+ (Isomer 1)

O-protonated (4-ABA)•(MeOH)7•H+ (Isomer 2)

O-protonated (4-ABA)•(MeOH)7•H+ (Isomer 3)

O-protonated (4-ABA)•(MeOH)8•H+ (Isomer 1)

O-protonated (4-ABA)•(MeOH)8•H+ (Isomer 2)

O-protonated (4-ABA)•(MeOH)8•H+ (Isomer 3)

Figure S5. Lowest Energy Solvent-bridged Structures

Bridged (4-ABA)•(MeOH)3•H+

Bridged (4-ABA)•(MeOH)4•H+

Bridged (4-ABA)•(MeOH)5•H+

Bridged (4-ABA)•(MeOH)6•H+ (Isomer 1)

Bridged (4-ABA)•(MeOH)6•H+ (Isomer 2)

Bridged (4-ABA)•(MeOH)7•H+ (Isomer 1)

Bridged (4-ABA)•(MeOH)7•H+ (Isomer 2)

Bridged (4-ABA)•(MeOH)8•H+ (Isomer 1)

Bridged (4-ABA)•(MeOH)8•H+ (Isomer 2)

Figure S6. Relative Gibbs’ Energies2

1

Figure S1. HDX results for D2O environments

Figure S1. (A) Ionogram of the separated tautomers of N- and O-protonated 4-ABA•H+ generated under different ESI solvent conditions (acetonitrile/water): blue = 100/0; red = 60/40; black = 0/100. (B) Mass spectrum displaying the isotope pattern for N-protonated 4-ABA (CV = −7.5V) before (dashed line) and moments after (solid green line) introduction of D2O to the throttle region. (C) Mass spectrum displaying the isotope pattern for O-protonated 4-ABA (CV = −1.5V) before (dashed line) and moments after (solid red line) introduction of D2O to the throttle region. (D) Same mass spectrum and CV as (B) after D2O has equilibrated. (E) Same mass spectrum and CV as (C) after D2O has equilibrated.

Figure S2. MS/MS results following H2O environment

Figure S2.(A) Ionogram of the separated tautomers of N- and O-protonated 4-ABA. (B) MS/MS spectrum for N-protonated 4-ABA (m/z 138; CV = −7.5V) with only N2 in the throttle gas. (C) MS/MS spectrum for O-protonated 4-ABA (m/z 138; CV = −1.5V) with only N2 in the throttle gas. (D) MS/MS spectrum for N-protonated 4-ABA (m/z 138; CV = −7.5V) with H2O in the throttle gas. (E) MS/MS spectrum for O-protonated 4-ABA (m/z 138; CV = −1.5V) with H2O in the throttle gas. All MS/MS spectra were obtained using a lab-frame collision energy of 30 eV.

1

Figure S3. Lowest Energy N-protonated Structures

N-protonated (4-ABA)•(MeOH)•H+

Electronic: −592.4797305hartree

ZPE corrected: −592.280748hartree

Enthalpy (298 K): −592.266474hartree

Gibbs (298 K): −592.323302hartree

XYZ Atomic Coordinates:

C 0.99499500 0.96164000 -0.40396600

C 0.14238300 1.65694500 0.44006900

C -1.16233300 1.19257500 0.59776600

C -1.58423100 0.05077600 -0.08652500

C -0.70291700 -0.63034400 -0.93277100

C 0.60032600 -0.17758300 -1.09638400

H 0.47162700 2.54496600 0.96925900

H -1.84897000 1.71661200 1.24884300

H -1.05368000 -1.51220600 -1.45429700

H 1.29055700 -0.70404400 -1.74607200

C -2.97609200 -0.49392900 0.04875600

O -3.35934600 -1.48492000 -0.51663900

O -3.73733700 0.25140500 0.87242700

H -4.62018200 -0.14785900 0.91679400

N 2.39501900 1.42369100 -0.56774000

H 2.58286900 2.24686900 0.00814000

H 3.06962200 0.64912500 -0.27755900

H 2.59120400 1.67801400 -1.53975800

C 3.34993800 -1.69149000 1.04336400

H 3.81272600 -1.65776300 2.03116600

H 2.28257200 -1.49593900 1.13327600

H 3.50075100 -2.66994400 0.58429300

O 3.89017500 -0.64705900 0.19159400

H 4.83542000 -0.78062300 0.05917600

N-protonated (4-ABA)•(MeOH)2•H+

Electronic: −708.2765045hartree

ZPE corrected: −708.024324hartree

Enthalpy (298 K): −708.005242hartree

Gibbs (298 K): −708.075053hartree

XYZ Atomic Coordinates:

C -0.52360500 -0.00529900 -0.82738500

C 0.13118100 1.20602800 -0.64264300

C 1.47608900 1.18996100 -0.28163500

C 2.14040000 -0.02785900 -0.11039500

C 1.45947800 -1.23324200 -0.30428300

C 0.11714200 -1.22871100 -0.66603500

H -0.39580500 2.14345700 -0.77586200

H 2.00942500 2.11924600 -0.13293800

H 1.99472200 -2.16472400 -0.16821200

H -0.42058200 -2.15723600 -0.81721600

C 3.58529100 -0.10118500 0.28107700

O 4.18055400 -1.13423700 0.45050300

O 4.14079900 1.11940000 0.42280900

H 5.07050400 1.00056000 0.67153600

N -1.94966400 0.00524300 -1.21829200

H -2.42831800 0.86344200 -0.85057800

H -2.04897800 -0.00201900 -2.23611900

H -2.44132800 -0.84020400 -0.83755100

C -2.76766900 2.62254600 1.25922500

H -3.64794100 2.39267100 1.86361500

H -1.93054400 2.00761700 1.58819700

H -2.50056000 3.67557100 1.36894000

O -2.99639800 2.29732700 -0.13185600

H -3.70147200 2.85020200 -0.48598800

C -2.73186800 -2.62240700 1.26724900

H -2.46097600 -3.67786800 1.33707200

H -1.88113800 -2.01616000 1.57656200

H -3.58551900 -2.40912900 1.91432000

O -3.01998300 -2.25999000 -0.10369800

H -3.74225100 -2.80111300 -0.44084000

N-protonated (4-ABA)•(MeOH)3•H+ (Isomer 1)

Electronic: −824.0707205hartree

ZPE corrected: −823.764378hartree

Enthalpy (298 K): −823.741334hartree

Gibbs (298 K): −823.821469hartree

XYZ Atomic Coordinates:

C -0.50406700 0.13080000 -1.02995200

C -1.56168100 0.85722300 -1.56228600

C -2.82225400 0.73107600 -0.98525600

C -3.00579300 -0.11197600 0.11451000

C -1.92661000 -0.83325900 0.63295100

C -0.66528000 -0.71634600 0.06074000

H -1.41513600 1.51267600 -2.41420300

H -3.66091500 1.28401700 -1.38630500

H -2.09304900 -1.48482300 1.48165500

H 0.17837800 -1.27663200 0.44582800

C -4.33813700 -0.28252200 0.77555600

O -4.52794900 -0.99361800 1.72964900

O -5.30388800 0.45091700 0.18399600

H -6.13418400 0.29260100 0.65885700

N 0.84177600 0.28460800 -1.60326400

H 1.43545700 -0.56640700 -1.43230800

H 0.80923100 0.47765300 -2.60422800

H 1.38025500 1.05802200 -1.11836500

C 2.87153800 -2.99243100 -1.01949300

H 3.07634700 -3.55204300 -0.10324500

H 2.00562100 -3.43234600 -1.51313500

H 3.73324800 -3.05090700 -1.68981300

O 2.53952200 -1.62423800 -0.71807500

H 3.26874200 -1.18510400 -0.24413900

C 4.26861600 -0.23709600 2.17556700

H 3.21830000 -0.35323200 2.43829600

H 4.80675400 -1.15680800 2.41334000

H 4.69331800 0.60080500 2.73199100

O 4.30601600 0.02426400 0.74758500

H 5.22303400 0.13254100 0.46758000

C 2.33040800 3.20530700 0.41127700

H 2.09496900 3.10300600 1.47414100

H 3.25138600 3.78011300 0.28671400

H 1.51613100 3.73421400 -0.08258800

O 2.44526100 1.91650600 -0.21871200

H 3.16755200 1.39510300 0.17554500

N-protonated (4-ABA)•(MeOH)3•H+ (Isomer 2)

Electronic: − 824.0703554hartree

ZPE corrected: −823.765375hartree

Enthalpy (298 K): −823.741244hartree

Gibbs (298 K): −823.824831hartree

XYZ Atomic Coordinates:

C 0.42284500 0.14171000 -0.02852500

C -0.24608000 -0.21323000 -1.19411400

C -1.62763500 -0.38290900 -1.15210300

C -2.32041700 -0.19430600 0.04734000

C -1.62740900 0.16502800 1.20750700

C -0.24846000 0.33619400 1.17468500

H 0.30273700 -0.35372300 -2.11768900

H -2.16817500 -0.65984600 -2.04729000

H -2.18330300 0.30687200 2.12597900

H 0.29901100 0.61524100 2.06715700

C -3.80426800 -0.36337400 0.14775400

O -4.43104300 -0.20586400 1.16471000

O -4.36414000 -0.71242200 -1.02994300

H -5.31945900 -0.80322400 -0.89164400

N 1.87567600 0.36342700 -0.07483400

H 2.31085600 0.10327900 0.83476600

H 2.31020800 -0.20205800 -0.83297400

H 2.05718600 1.37676100 -0.25950800

C 2.26892900 -1.63627600 3.04906400

H 1.97656200 -1.47596500 4.08933800

H 1.39136300 -1.93791800 2.47800900

H 3.02691800 -2.42112300 2.99025500

O 2.74484700 -0.40867000 2.45514800

H 3.49706100 -0.07511800 2.95542700

C 2.43025600 -2.65829200 -2.20832700

H 1.57717800 -2.79068600 -1.54333700

H 2.13858800 -2.94780300 -3.22049100

H 3.25760500 -3.28382400 -1.86444400

O 2.78004700 -1.25800000 -2.15619000

H 3.50414400 -1.08076200 -2.76591300

C 0.69273600 3.76604100 -0.66725600

H 0.61114900 4.54562400 0.09369600

H 0.57495200 4.19882600 -1.66343000

H -0.08750500 3.02389500 -0.50396700

O 1.95377200 3.06860200 -0.55542500

H 2.68234700 3.68487400 -0.68265500

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 1)

Electronic: − 939.8620327hartree

ZPE corrected: −939.502661hartree

Enthalpy (298 K): −939.474576hartree

Gibbs (298 K): −939.568363hartree

XYZ Atomic Coordinates:

C -0.65812200 0.35266500 -0.28146800

C -1.59743900 1.30060100 0.10843800

C -2.92450300 0.91044000 0.26400400

C -3.29552600 -0.41727200 0.03052000

C -2.33497300 -1.35351600 -0.36335700

C -1.00782800 -0.97215600 -0.52175000

H -1.29751900 2.32801600 0.27931100

H -3.67167300 1.63278000 0.56411800

H -2.64469900 -2.37526700 -0.54404000

H -0.25364300 -1.68550600 -0.83271400

C -4.70570600 -0.89025000 0.18350900

O -5.06004500 -2.02738200 -0.00288600

O -5.54610400 0.09967300 0.55646300

H -6.43496400 -0.27919900 0.63366100

N 0.74692700 0.75330800 -0.41175100

H 1.25028700 0.64580900 0.50452300

H 1.26637900 0.11807600 -1.05318100

H 0.83219400 1.73866400 -0.73047400

C 1.78239300 4.39754500 -0.55333400

H 1.29077600 5.31351200 -0.21715100

H 2.24755900 3.90984300 0.30316600

H 2.55220700 4.63601100 -1.29158900

O 0.82025300 3.46451700 -1.08742200

H 0.37662000 3.85310300 -1.84882200

C 2.62179000 -1.76144900 -2.84104600

H 2.57013900 -2.85381600 -2.85359800

H 1.90419900 -1.36944100 -3.56137700

H 3.62623100 -1.43777900 -3.12964200

O 2.25685200 -1.24283200 -1.55193800

H 2.85495800 -1.58296200 -0.86362800

C 5.24211100 -1.61702900 0.64699300

H 5.75714500 -2.29018000 -0.04156900

H 5.30975000 -0.59550400 0.27631800

H 5.69719500 -1.67379700 1.63793600

O 3.82778600 -1.93448700 0.71253000

H 3.71815600 -2.83142800 1.05025500

C 2.00167300 0.22977000 3.18876100

H 1.46843200 -0.66205100 3.53086100

H 2.93234400 0.34254400 3.75137300

H 1.37687000 1.10451500 3.36698900

O 2.26197100 0.17351300 1.77613600

H 2.81363900 -0.59921000 1.56084200

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 2)

Electronic: − 939.859926hartree

ZPE corrected: −939.501338hartree

Enthalpy (298 K): −939.472899hartree

Gibbs (298 K): −939.567741hartree

XYZ Atomic Coordinates:

C -1.29352400 0.27377800 -0.02166900

C -0.63935100 -0.55718500 -0.92227300

C 0.75355000 -0.59700100 -0.90912000

C 1.47036300 0.18730700 -0.00212200

C 0.78968400 1.01502700 0.89619900

C -0.59911400 1.06145900 0.89154000

H -1.20709700 -1.15853700 -1.62253000

H 1.28763600 -1.23198700 -1.60337900

H 1.36485600 1.61697800 1.58857500

H -1.13565800 1.70415200 1.58008700

C 2.97104000 0.18252700 0.03523800

O 3.60189000 0.87810100 0.80813700

O 3.51284600 -0.64443000 -0.85070600

H 4.50950500 -0.57414800 -0.78231300

N -2.76417100 0.30767500 -0.00164100

H -3.10559800 -0.22796000 0.82511000

H -3.10071900 1.29299400 0.04645400

H -3.16593100 -0.16076200 -0.83858100

C -4.31208100 -2.57904100 -1.49728100

H -3.89187100 -3.43075100 -2.03739500

H -4.02393100 -2.63993900 -0.44734200

H -5.40232600 -2.59162100 -1.57118200

O -3.77216000 -1.33642900 -1.99780200

H -4.03191900 -1.20878300 -2.91616700

C -2.41198700 3.92589200 -0.58617900

H -2.11967600 4.75836400 0.05797700

H -1.52424300 3.35135600 -0.84773500

H -2.88033800 4.30413600 -1.49807200

O -3.29573100 3.02236900 0.11451300

H -4.08919800 3.49221500 0.39147400

C 7.23840700 -0.82465700 -0.12965800

H 7.13696200 -1.45527500 0.75918500

H 7.41786200 -1.45659100 -0.99854200

H 8.08629300 -0.14586400 -0.00530200

O 6.03389500 -0.08961100 -0.39235300

H 5.81526200 0.49621000 0.34541100

C -2.15210100 -2.19962300 2.52003000

H -1.82764100 -1.75094300 3.46197600

H -2.35706200 -3.26311800 2.66229200

H -1.36358100 -2.08150100 1.77799600

O -3.31675100 -1.52117300 1.99480800

H -4.04362100 -1.59386300 2.62249000

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 3)

Electronic: − 939.8602194hartree

ZPE corrected: −939.500547hartree

Enthalpy (298 K): −939.473029hartree

Gibbs (298 K): −939.565108hartree

XYZ Atomic Coordinates:

C 0.54189300 -0.11180400 1.03956700

C -0.39855000 -0.88458200 1.70898900

C -1.73037000 -0.81753600 1.30978700

C -2.10242900 0.01326300 0.24925900

C -1.13839800 0.78141500 -0.40833300

C 0.19433300 0.72417900 -0.01538400

H -0.10631900 -1.53085400 2.53006500

H -2.48293000 -1.40678600 1.81629700

H -1.44990400 1.42102400 -1.22461600

H 0.95045400 1.31996600 -0.51301700

C -3.52652300 0.10888300 -0.21637200

O -3.85775200 0.81947400 -1.14614000

O -4.35668100 -0.65311200 0.48484800

H -5.27925000 -0.54694100 0.10906600

N 1.95935000 -0.20439000 1.42472400

H 2.45803100 -0.96689100 0.88450400

H 2.49094600 0.66313500 1.16533300

H 2.06992300 -0.37907200 2.42351400

C -7.87871600 0.31424200 -0.47510800

H -8.49983500 0.44219600 -1.36558400

H -8.31549900 -0.46337900 0.15019200

H -7.84367300 1.25191300 0.08843800

O -6.56233200 -0.13205600 -0.83417100

H -6.11707700 0.51815800 -1.39490400

C 3.79147900 3.12728300 0.48720100

H 3.76770100 3.65420600 -0.47027000

H 3.02311300 3.54500000 1.13696900

H 4.76858500 3.26124500 0.95941000

O 3.48734100 1.73209100 0.31123800

H 4.12469000 1.30903700 -0.29186500

C 6.53100400 -0.03465500 -0.87870400

H 7.08349100 0.88353700 -1.08806100

H 6.51222300 -0.21187300 0.19534300

H 7.00605900 -0.88144200 -1.37791000

O 5.14592900 0.09492100 -1.29576400

H 5.11353100 0.24293000 -2.24859300

C 3.22777200 -3.11232600 -0.71992000

H 2.77087400 -3.00836900 -1.70785400

H 4.16761800 -3.66416500 -0.79997400

H 2.54958200 -3.66614100 -0.07178400

O 3.44374500 -1.82657000 -0.10998200

H 4.05124800 -1.28386300 -0.64390600

N-protonated (4-ABA)•(MeOH)4•H+ (Isomer 4)

Electronic: − 939.859955hartree

ZPE corrected: −939.500475hartree

Enthalpy (298 K): −939.472938hartree

Gibbs (298 K): −939.565498hartree

XYZ Atomic Coordinates:

C -1.09879900 -0.22825300 0.85343200

C -2.08487000 0.27529300 1.69262900

C -3.38782400 0.38400300 1.21391200

C -3.68552700 -0.00504800 -0.09506000

C -2.67744300 -0.50912300 -0.92254900

C -1.37534400 -0.62504700 -0.45108400

H -1.85073700 0.57884200 2.70755400

H -4.17113500 0.76848900 1.85313200

H -2.93106600 -0.81016300 -1.93133300

H -0.58617000 -1.02476200 -1.07692900

C -5.06690900 0.09291200 -0.66156300

O -5.35626100 -0.22443900 -1.78765800

O -5.95690200 0.57894200 0.22972600

H -6.82421000 0.61195400 -0.20207000

N 0.28897000 -0.31762400 1.32390800

H 0.83530100 0.52868100 0.99968100

H 0.34094900 -0.37267300 2.34047200

H 0.78037500 -1.16350400 0.89987900

C 0.88851500 3.03916800 -0.00627100

H 1.46861600 3.92457000 0.26693000

H 0.66152500 3.05897100 -1.07599000

H -0.04784600 3.04737100 0.55141300

O 1.59089200 1.83692400 0.35426800

H 2.42512200 1.77198300 -0.14608200

C 1.48199800 -3.62646000 -0.12329100

H 1.87716900 -3.96893400 -1.08316300

H 2.01490600 -4.12521000 0.69181400

H 0.42438700 -3.88477300 -0.06735400

O 1.58464600 -2.19829800 -0.01689700

H 2.52001700 -1.90055400 -0.09818100

C 5.10195000 2.39982800 -0.35973900

H 4.95280300 3.46509300 -0.54738300

H 5.02880800 2.20607400 0.70915100

H 6.08449500 2.08909000 -0.72083600

O 4.05454500 1.61602100 -0.98825700

H 4.07527800 1.75942900 -1.94192500

C 5.31105100 -1.68068000 0.02759800

H 5.99480400 -1.07109900 0.62596200

H 5.18312600 -2.64386800 0.52104700

H 5.73980000 -1.84639800 -0.96549400

O 4.01495400 -1.06950800 -0.05600400

H 4.08512200 -0.19193500 -0.46717200

N-protonated (4-ABA)•(MeOH)5•H+ (Isomer 1)

Electronic: −1055.6510208hartree

ZPE corrected: −1055.238422hartree

Enthalpy (298 K): −1055.205759hartree

Gibbs (298 K): −1055.312447hartree

XYZ Atomic Coordinates:

C 0.34034200 0.51821800 -0.29693500

C -0.52687000 1.51235900 0.14200100

C -1.89210900 1.24466100 0.18410000

C -2.37408600 -0.00757500 -0.20842800

C -1.48406300 -0.99182600 -0.64634600

C -0.11851800 -0.73357900 -0.69306700

H -0.14170700 2.48185700 0.43649100

H -2.58791900 2.00323800 0.51682400

H -1.87905500 -1.95262000 -0.95183900

H 0.58217000 -1.48507200 -1.03763000

C -3.83777100 -0.33185100 -0.18551800

O -4.27007900 -1.41585600 -0.53048900

O -4.59092800 0.67570400 0.24298600

H -5.54905100 0.39051100 0.21185800

N 1.78286200 0.78919100 -0.31623600

H 2.21775100 0.55510300 0.61010900

H 2.27806800 0.16476300 -0.98608600

H 1.97433300 1.78432600 -0.54450200

C 3.12850700 4.37232500 -0.25812300

H 2.69728100 5.28717100 0.15546200

H 3.59999800 3.80789300 0.54610900

H 3.88141700 4.62136500 -1.01028600

O 2.10136900 3.52411000 -0.81089300

H 1.64947800 3.98270400 -1.52713900

C 3.53645300 -1.67319100 -2.88920800

H 3.36148200 -2.74668900 -3.00460900

H 2.90346900 -1.13802400 -3.59661300

H 4.58386300 -1.44600800 -3.10906500

O 3.17139700 -1.22936000 -1.57319700

H 3.69218200 -1.69489500 -0.89578400

C 5.96307900 -2.09718200 0.74057900

H 6.46735800 -2.74389900 0.01943000

H 6.14098300 -1.05480000 0.48130200

H 6.34186700 -2.28988700 1.74643800

O 4.52635800 -2.29147100 0.68704500

H 4.31947300 -3.20371800 0.92247200

C 2.72977000 -0.22303400 3.26764000

H 2.05708700 -1.06536400 3.45474600

H 3.61514100 -0.30861900 3.90350400

H 2.21179600 0.70364200 3.51319100

O 3.10089500 -0.14861100 1.88115400

H 3.58145000 -0.95168400 1.61376600

C -8.07480400 -0.72237400 0.76622800

H -8.49850100 0.24681600 1.02664200

H -7.78842000 -1.24732800 1.68326400

H -8.82880400 -1.30447700 0.22943800

O -6.93786100 -0.46796600 -0.07078500

H -6.51201100 -1.29475000 -0.33793500

N-protonated (4-ABA)•(MeOH)5•H+ (Isomer 2)

Electronic: −1055.6505444hartree

ZPE corrected: −1055.237882hartree

Enthalpy (298 K): −1055.205247hartree

Gibbs (298 K): −1055.31215hartree

XYZ Atomic Coordinates:

C 0.98054200 0.46418300 -0.07839300

C 1.96028300 0.84206300 0.83502400

C 3.14381800 0.11428000 0.89897400

C 3.33606800 -0.98272000 0.05225100

C 2.34064700 -1.34505000 -0.85906900

C 1.15486300 -0.62122700 -0.92985600

H 1.80366800 1.70039100 1.47827500

H 3.91802900 0.39386000 1.60086400

H 2.51095900 -2.19477300 -1.50834100

H 0.37871900 -0.88537300 -1.63816900

C 4.58726100 -1.80007200 0.07971500

O 4.78532300 -2.75751600 -0.62561700

O 5.48119500 -1.34861000 0.98779800

H 6.26011200 -1.92404200 0.94707400

N -0.27084800 1.22608000 -0.12600600

H -0.86740800 0.99103900 0.70409700

H -0.06946700 2.24487400 -0.12074900

H -0.83825500 0.98142800 -0.97810800

C -1.29713200 0.35221600 3.34517300

H -2.04898700 0.62131700 4.09253300

H -0.93891500 -0.66502900 3.53055200

H -0.45704800 1.04104900 3.43506100

O -1.82153600 0.48797300 2.01589300

H -2.59424600 -0.09475900 1.90477000

C 1.87898600 4.16151400 -0.79356200

H 2.38229900 3.21049800 -0.96400000

H 1.66063100 4.63208600 -1.75567700

H 2.53203100 4.80774000 -0.20197000

O 0.66510900 3.86056700 -0.07306900

H 0.19746500 4.67704200 0.13071000

C -2.19279700 0.92206900 -3.42419500

H -2.32763200 0.15869200 -4.19591500

H -3.12208400 1.48806100 -3.30760400

H -1.40039100 1.60060700 -3.74220000

O -1.78440600 0.32821000 -2.18528700

H -2.49061900 -0.26669300 -1.84339400

C -5.34742900 -0.35156000 1.92567300

H -5.43641600 -0.11632800 2.98831200

H -5.26570900 0.57141800 1.35447500

H -6.22296300 -0.91015100 1.58867200

O -4.13147200 -1.10037900 1.66612700

H -4.16258000 -1.93533100 2.14795200

C -4.08270400 -2.51588800 -1.72385300

H -5.14976400 -2.69811500 -1.56490300

H -3.89815700 -2.44866400 -2.79580900

H -3.50233700 -3.35113300 -1.31887300

O -3.68101400 -1.26675100 -1.14430000

H -3.83502700 -1.27906200 -0.18525900

N-protonated (4-ABA)•(MeOH)5•H+ (Isomer 3)

Electronic: −1055.6492455hartree

ZPE corrected: −1055.236535hartree

Enthalpy (298 K): −1055.204406hartree

Gibbs (298 K): −1055.309683hartree

XYZ Atomic Coordinates:

C 0.03506800 -0.41189300 -1.01935700

C 0.98243800 -0.03863900 -1.96429500

C 2.31916100 0.04247100 -1.58288900

C 2.68975200 -0.24259500 -0.26605700

C 1.71908000 -0.61662700 0.66754500

C 0.38262200 -0.70504400 0.29539600

H 0.69184900 0.18532900 -2.98540800

H 3.07652900 0.32366600 -2.30224000

H 2.02977700 -0.84106600 1.68026200

H -0.37923100 -1.00507900 1.00525700

C 4.11935400 -0.17166800 0.18434800

O 4.45293200 -0.42094200 1.32728600

O 4.95484000 0.18495200 -0.78416600

H 5.88536700 0.18870700 -0.41545800

N -1.38663300 -0.46165400 -1.38676900

H -1.86147600 0.43204600 -1.08124600

H -1.51375000 -0.58072600 -2.39098700

H -1.88616200 -1.24752200 -0.87096700

C -1.52824200 2.86892000 0.00617200

H -1.96456800 3.85607500 -0.16761900

H -1.26215000 2.76000600 1.06158900

H -0.62411300 2.77325900 -0.59464700

O -2.43105000 1.83042600 -0.41267200

H -3.24858100 1.86255900 0.11697700

C 8.33141800 0.83816100 0.81392900

H 8.80852100 1.01795300 -0.14867900

H 8.02939500 1.79574900 1.24994500

H 9.04648200 0.34150200 1.47522700

O 7.19843700 -0.00637000 0.56466100

H 6.72722800 -0.20750900 1.38505800

C -2.64325400 -3.57450400 0.42572500

H -2.97048500 -3.79848200 1.44445400

H -3.26951800 -4.11797600 -0.28818200

H -1.60900500 -3.89894900 0.31004400

O -2.68149500 -2.16048000 0.18310300

H -3.58884500 -1.79922600 0.30651900

C -5.86643500 2.67927500 0.35433400

H -5.62490600 3.74139800 0.43094400

H -5.85475600 2.37991900 -0.69237800

H -6.85446300 2.48753900 0.77796800

O -4.85885700 1.87400000 1.01954200

H -4.83482300 2.10125100 1.95663600

C -6.36473700 -1.39591300 0.30799100

H -7.03611600 -0.77874000 -0.29674400

H -6.32242200 -2.39310100 -0.12961200

H -6.75571400 -1.47339200 1.32717200

O -5.02988400 -0.86926000 0.29686500

H -5.02434700 0.03611300 0.64947700

N-protonated (4-ABA)•(MeOH)6•H+ (Isomer 1)

Electronic: −1171.4436208hartree

ZPE corrected: −1170.976073hartree

Enthalpy (298 K): −1170.939969hartree

Gibbs (298 K): −1171.052384hartree

XYZ Atomic Coordinates:

C 0.02404000 0.51560800 -0.17589700

C -0.85435000 1.52747200 -0.54354800

C -2.22368400 1.27555100 -0.50414100

C -2.69495100 0.02320400 -0.10271200

C -1.79070100 -0.98120300 0.25553300

C -0.42200200 -0.74174500 0.22029600

H -0.47730600 2.49171100 -0.86282500

H -2.92885500 2.04567500 -0.78684800

H -2.17764300 -1.94643200 0.55735800

H 0.28838700 -1.51843100 0.48121100

C -4.16104800 -0.28845600 -0.05089300

O -4.58282700 -1.37840400 0.28797900

O -4.92726200 0.73607800 -0.40935500

H -5.88412000 0.44707300 -0.36453400

N 1.47248900 0.76666700 -0.22132400

H 1.68477800 1.77156300 -0.38167000

H 1.94621000 0.48058700 0.66126500

H 1.93088800 0.19064300 -0.96187000

C 6.17769900 0.47945500 -0.52674100

H 6.39588100 0.93628200 -1.49603000

H 6.57340100 1.12118100 0.26010500

H 6.66442600 -0.49881800 -0.46678000

O 4.76053300 0.37331200 -0.31788500

H 4.35384600 -0.18448700 -1.00671500

C -8.47651500 -0.19046700 0.50028400

H -8.29225900 -0.03365600 1.56797400

H -8.89546100 0.71942000 0.07221500

H -9.19243100 -1.00590000 0.36634500

O -7.25886500 -0.46125300 -0.20868100

H -6.83384500 -1.26277600 0.12770100

C 3.45732900 0.10339300 3.11716100

H 2.58109100 -0.17966700 3.69960500

H 4.32920100 -0.43331900 3.49997000

H 3.62048500 1.18036100 3.21483000

O 3.19740800 -0.25419400 1.74741400

H 3.95600900 -0.00720700 1.16532300

C 2.69367400 -1.61596400 -3.05232900

H 1.67526500 -1.99349200 -3.17678100

H 2.85509900 -0.78745200 -3.74139500

H 3.41003900 -2.41032600 -3.27646800

O 2.89219800 -1.11275000 -1.71744500

H 2.74819300 -1.82752000 -1.05039100

C 2.71884700 -3.93843400 0.84103500

H 2.23874300 -4.18855900 1.79094500

H 2.31007300 -4.58082000 0.06172300

H 3.79651700 -4.11175000 0.91814200

O 2.43290300 -2.58095000 0.46631700

H 2.76164900 -1.95778500 1.14145900

C 1.39825700 4.41852700 0.55612600

H 0.64653200 3.87572100 1.12909000

H 2.22277400 4.69755500 1.21723400

H 0.94013300 5.31531700 0.13238600

O 1.84507100 3.52735800 -0.48652500

H 2.49203700 3.97340100 -1.04292100

N-protonated (4-ABA)•(MeOH)6•H+ (Isomer 2)

Electronic: −1171.4395924hartree

ZPE corrected: −1170.973396hartree

Enthalpy (298 K): −1170.936375hartree

Gibbs (298 K): −1171.054066hartree

XYZ Atomic Coordinates:

C -0.01652800 0.86488600 -0.04708100

C 0.89695800 1.32978300 0.89421800

C 2.19672000 0.83482600 0.87775300

C 2.57131000 -0.11768600 -0.07566900

C 1.64000200 -0.56754400 -1.01458500

C 0.33761700 -0.07747600 -1.00608400

H 0.59730200 2.07494400 1.62231100

H 2.92417000 1.18118800 1.59972900

H 1.95163000 -1.30148800 -1.74718100

H -0.39247900 -0.41184400 -1.73362000

C 3.95891400 -0.68223700 -0.12222900

O 4.29377100 -1.52456500 -0.93440300

O 4.76431800 -0.17179500 0.80435700

H 5.66151600 -0.60478100 0.71648400

N -1.39380200 1.36805800 -0.00179800

H -1.90226100 0.92608500 0.80141500

H -1.39520300 2.39926500 0.11703100

H -1.92751500 1.10884600 -0.86959600

C -1.90998500 -0.23217400 3.28530500

H -2.59453700 -0.28731200 4.13656300

H -1.33747700 -1.16179700 3.20951900

H -1.21659300 0.59241900 3.45011300

O -2.62242800 0.04434900 2.06982600

H -3.26806000 -0.66474400 1.90024200

C 0.14596000 4.70081900 -0.36699500

H 0.78765300 3.87689300 -0.67726400

H -0.18822000 5.25103400 -1.25045200

H 0.71259100 5.36295900 0.29235900

O -0.96963200 4.11095000 0.33283600

H -1.55792000 4.80358200 0.65041300

C -3.37659400 1.00891900 -3.27484400

H -3.37812000 0.31997800 -4.12455100

H -4.40186400 1.33083100 -3.06776000

H -2.77618100 1.88096700 -3.53660300

O -2.77825200 0.39931900 -2.12442200

H -3.30490100 -0.38206400 -1.83957800

C -5.90259000 -1.51155800 1.93081800

H -5.99511900 -1.40952500 3.01409500

H -6.04312900 -0.53969600 1.46114200

H -6.65253400 -2.20891800 1.55205100

O -4.56705300 -1.94985000 1.56940300

H -4.40037600 -2.81636600 1.95865300

C -4.19336800 -2.98404100 -1.92991800

H -5.15190300 -3.49291600 -1.79075100

H -4.06234100 -2.77542900 -2.99153900

H -3.37905700 -3.63563000 -1.59655000

O -4.17361900 -1.72484600 -1.24377200

H -4.29675400 -1.86383900 -0.29016300

C 8.25933800 -1.27529000 -0.10216100

H 8.71273600 -0.81837200 0.77667300

H 8.30048500 -0.56783300 -0.93665800

H 8.81879800 -2.17902600 -0.35867000

O 6.90563900 -1.59701700 0.24777700

H 6.44378300 -2.00355900 -0.49927100

N-protonated (4-ABA)•(MeOH)7•H+ (Isomer 1)

Electronic: −1287.241161hartree

ZPE corrected: −1286.719438hartree

Enthalpy (298 K): −1286.67974hartree

Gibbs (298 K): −1286.800084hartree

XYZ Atomic Coordinates:

C 1.85202400 -0.02542700 -0.08539500

C 2.53793000 -0.58382500 -1.15831100

C 3.92982900 -0.59663600 -1.13897000

C 4.61997800 -0.05400600 -0.05114200

C 3.91293100 0.50321600 1.01887600

C 2.52393100 0.52008300 1.00435200

H 1.99207900 -1.00315600 -1.99596600

H 4.48076600 -1.02749200 -1.96418000

H 4.46646900 0.91791100 1.85203000

H 1.97020600 0.95386900 1.82951900

C 6.11309900 -0.04382100 0.02209000

O 6.74046400 0.41365400 0.94445600

O 6.68862700 -0.60578600 -1.06332700

H 7.64968500 -0.56282200 -0.94486400

N 0.39190800 0.00947000 -0.11722600

H -0.00359800 -0.74867400 -0.73313600

H -0.02897300 -0.12712300 0.82410100

H 0.03474200 0.92352100 -0.50249600

C -4.50734600 -1.40603400 -2.18369500

H -5.46017600 -1.13236100 -1.72247600

H -4.43024200 -0.94390200 -3.17132400

H -4.46470400 -2.48929200 -2.29508000

O -3.40199600 -1.01335100 -1.34760400

H -3.42568100 -0.03715400 -1.20140500

C -0.67545400 -3.26471700 -1.45456300

H -1.07485200 -3.83822600 -2.29531000

H 0.38507000 -3.49478300 -1.34955400

H -1.19901100 -3.53697800 -0.53347300

O -0.78357000 -1.85243400 -1.70822200

H -1.72771700 -1.60120400 -1.74515200

C -4.48484500 2.46507100 -1.11394200

H -4.28524600 3.51160300 -0.86852900

H -4.65408100 2.37841100 -2.18714600

H -5.37828000 2.13214900 -0.57919900

O -3.35171100 1.63907200 -0.78183700

H -3.17614900 1.69180500 0.19802700

C -3.91136600 -2.75890000 1.79923200

H -4.38555400 -3.55126400 1.21357900

H -3.51375400 -3.19500000 2.71549200

H -4.65572700 -1.99957700 2.05889000

O -2.80685300 -2.18609200 1.08095200

H -3.12314400 -1.80970100 0.23426900

C -0.62729500 -0.87945400 3.49998200

H -1.45133500 -0.95838600 4.21390500

H -0.09851000 -1.83445900 3.44237400

H 0.06374700 -0.10921000 3.84266000

O -1.11267300 -0.48472200 2.20258000

H -1.74185700 -1.17179100 1.85384200

C -1.96765000 2.97626800 2.13398800

H -1.05668600 3.11456900 1.54240800

H -1.72585700 2.96592100 3.20012900

H -2.64372000 3.80946600 1.94193600

O -2.65313000 1.77134700 1.75551100

H -2.11926300 0.99763000 2.02579200

C -0.18263400 3.10701700 -2.18025900

H -0.61916100 4.10902700 -2.14934300

H 0.89456400 3.19019100 -2.03725200

H -0.37903500 2.65110600 -3.15541200

O -0.69351700 2.29608100 -1.11042100

H -1.66228400 2.18393500 -1.18725000

N-protonated (4-ABA)•(MeOH)7•H+ (Isomer 2)

Electronic: −1287.2289881hartree

ZPE corrected: −1286.709703hartree

Enthalpy (298 K): −1286.669304hartree

Gibbs (298 K): −1286.79537hartree

XYZ Atomic Coordinates:

C -0.73826900 0.95597700 -0.30038200

C 0.08791200 1.76546500 0.47353600

C 1.43726900 1.44690300 0.58334000

C 1.94934100 0.32549300 -0.07778300

C 1.10313100 -0.47152300 -0.85195600

C -0.24854300 -0.16053600 -0.96834700

H -0.31710200 2.63814400 0.97322600

H 2.09956400 2.06250700 1.17729900

H 1.51875400 -1.33235400 -1.36031700

H -0.91360000 -0.76711600 -1.57170500

C 3.40002400 -0.04889700 0.02105400

O 3.84092300 -1.03039300 -0.56029800

O 4.09941600 0.77051700 0.77436300

H 5.09041100 0.51459900 0.82929400

N -2.16451100 1.28669600 -0.39184800

H -2.64330000 1.04919600 0.51010000

H -2.28370500 2.30003300 -0.58393600

H -2.64294400 0.72464100 -1.14053900

C -2.64921300 0.74552700 3.23296800

H -3.36477700 0.88839500 4.04773400

H -1.98195500 -0.08942900 3.46804900

H -2.05222900 1.65189900 3.13225600

O -3.32645400 0.53904400 1.98413400

H -3.89057400 -0.25262800 2.04267300

C -0.97478900 4.52886500 -1.69940900

H -0.23507200 3.73072800 -1.74932200

H -1.32081400 4.76472800 -2.70911800

H -0.51489600 5.41115300 -1.24737000

O -2.05559900 4.03612100 -0.87978200

H -2.73022000 4.71651400 -0.78697600

C -4.00318800 -0.20221200 -3.40741700

H -3.94653000 -1.10795400 -4.01823100

H -5.05095600 0.09339700 -3.29486000

H -3.46162900 0.59474800 -3.91838400

O -3.37756600 -0.40487500 -2.13433800

H -3.85350600 -1.10240000 -1.62858400

C -6.43513400 -1.30344200 2.32729700

H -6.56591900 -0.90158700 3.33419500

H -6.65184000 -0.52751500 1.59533000

H -7.10705900 -2.14930200 2.16838200

O -5.05576800 -1.69744200 2.10738800

H -4.82014800 -2.39374500 2.73168500

C -4.64252400 -3.65753900 -0.96682100

H -5.58392000 -4.13251700 -0.67465600

H -4.52839000 -3.74893100 -2.04678900

H -3.80581800 -4.16943000 -0.48044700

O -4.65356800 -2.25712400 -0.65777400

H -4.76321200 -2.12827500 0.29882500

C 7.23149500 0.12121700 2.21028600

H 6.99565500 1.04202600 2.74469400

H 8.31606100 0.05390200 2.08830600

H 6.87859800 -0.73471800 2.79514200

O 6.58596700 0.18478300 0.93358100

H 6.73360100 -0.65339000 0.43172100

C 7.05675500 -2.41725300 -1.69202300

H 8.11322400 -2.58845900 -1.48462700

H 6.96664800 -1.61425400 -2.43222400

H 6.62710900 -3.33683100 -2.10209900

O 6.43127700 -2.06665000 -0.45500700

H 5.48744000 -1.87275000 -0.59998400

N-protonated (4-ABA)•(MeOH)8•H+ (Isomer 1)

Electronic: −1403.0301761hartree

ZPE corrected: −1402.454998hartree

Enthalpy (298 K): −1402.410843hartree

Gibbs (298 K): −1402.543076hartree

XYZ Atomic Coordinates:

C 1.03834900 0.03963300 -0.03950200

C 1.75119900 -0.49008300 -1.10933500

C 3.14261300 -0.45911300 -1.07595400

C 3.80615200 0.09702300 0.02121100

C 3.07169900 0.62265900 1.08800500

C 1.68245100 0.59650700 1.06091400

H 1.22639100 -0.91947000 -1.95542800

H 3.71799900 -0.86431300 -1.89756900

H 3.60520700 1.04900500 1.92823100

H 1.10752300 1.00715400 1.88362000

C 5.30228800 0.15474400 0.09318600

O 5.89020900 0.64583000 1.03901400

O 5.89927600 -0.37688500 -0.96838300

H 6.88859600 -0.28700200 -0.85328700

N -0.42273500 0.03471700 -0.08867300

H -0.78934500 -0.73467700 -0.70713000

H -0.85166300 -0.11052400 0.84679500

H -0.79796700 0.93717900 -0.48128300

C 9.56866800 -0.65755800 -0.09195900

H 9.38862500 -1.50045000 0.58313400

H 9.84750900 -1.03905100 -1.07349700

H 10.38809000 -0.04555400 0.29479700

O 8.38528300 0.13263300 -0.27348000

H 8.07947100 0.49586600 0.56983000

C -5.25293600 -1.49873800 -2.23735200

H -6.21974600 -1.24418800 -1.79449600

H -5.16742700 -1.03713500 -3.22457300

H -5.18570100 -2.58110300 -2.34546000

O -4.17180400 -1.08152600 -1.38223900

H -4.21776700 -0.10552000 -1.23943700

C -1.38679800 -3.27041400 -1.43090600

H -1.74926900 -3.85826600 -2.27855100

H -0.32317300 -3.47018800 -1.29880500

H -1.92491100 -3.55421400 -0.52165000

O -1.52756500 -1.86294000 -1.69316700

H -2.47667100 -1.63617100 -1.74879200

C -5.34752400 2.36161600 -1.16694100

H -5.18462200 3.41386300 -0.91878400

H -5.50305900 2.27079400 -2.24190000

H -6.23530700 1.99962000 -0.64159100

O -4.19206300 1.57230600 -0.82411600

H -4.02597700 1.63301500 0.15689800

C -4.71285000 -2.80870800 1.76374900

H -5.16440700 -3.61382200 1.17752000

H -4.32997600 -3.22907700 2.69357600

H -5.47220100 -2.05601900 1.99840100

O -3.60046900 -2.23027300 1.06294000

H -3.90414200 -1.86541700 0.20659100

C -1.48619000 -0.87762900 3.51501800

H -2.32048200 -0.97270000 4.21505300

H -0.93708800 -1.82171200 3.46772500

H -0.81670800 -0.09331000 3.86842500

O -1.95693200 -0.49408900 2.20931800

H -2.56513500 -1.19416000 1.85018400

C -2.85627800 2.95049100 2.09453200

H -1.93962000 3.09404100 1.51322800

H -2.62857700 2.95412000 3.16385100

H -3.53988600 3.77325900 1.88480400

O -3.52196900 1.73337800 1.71986500

H -2.98173400 0.96916100 2.00465600

C -1.02122400 3.10711100 -2.17607100

H -1.46864000 4.10468800 -2.15817100

H 0.05217700 3.20177800 -2.01306200

H -1.19407300 2.64486200 -3.15271400

O -1.54362500 2.29561800 -1.11236500

H -2.50762000 2.16493800 -1.21109200

N-protonated (4-ABA)•(MeOH)8•H+ (Isomer 2)

Electronic: −1403.0222371hartree

ZPE corrected: −1402.447531hartree

Enthalpy (298 K): −1402.402867hartree

Gibbs (298 K): −1402.536406hartree

XYZ Atomic Coordinates:

C 0.23325700 0.61846800 -0.53281500

C -0.35165700 -0.47865900 -1.15478100

C -1.72499300 -0.67095600 -1.02705500

C -2.49484900 0.22730600 -0.28251300

C -1.88599000 1.32756600 0.32872700

C -0.51587200 1.52854500 0.20646200

H 0.25859600 -1.16217400 -1.73411600

H -2.20657800 -1.51336100 -1.50537300

H -2.50053500 2.01669100 0.89407500

H -0.03360200 2.38008900 0.67358200

C -3.97716800 0.04719300 -0.12330500

O -4.64525600 0.84585500 0.51824800

O -4.44054900 -1.02361600 -0.72827700

H -5.45533700 -1.12916000 -0.62939900

N 1.68342700 0.79884700 -0.61459300

H 2.13247600 0.40482800 0.23215800

H 2.10070800 0.27639800 -1.41820600

H 1.96554600 1.80512100 -0.65834700

C 1.34179700 -1.11531100 2.48241500

H 1.58600200 -1.97390000 3.11332200

H 1.02384200 -0.27627300 3.10600100

H 0.52933200 -1.38131800 1.80736800

O 2.46848600 -0.74394500 1.66006300

H 3.22094300 -0.45922400 2.21284600

C 3.41263900 -1.03180200 -3.65052800

H 2.84954200 -0.36792400 -4.30659600

H 4.45466000 -0.69658100 -3.61496000

H 3.37303300 -2.04498500 -4.06087100

O 2.80134000 -0.97772700 -2.35686100

H 3.27540400 -1.55137600 -1.71810900

C 2.88186100 4.58209800 -0.88469900

H 3.33890600 5.27840700 -0.17600700

H 3.48018100 4.54849600 -1.80076800

H 1.88097300 4.93698100 -1.12899600

O 2.73968900 3.27982100 -0.30186300

H 3.60272000 2.89209300 -0.06930900

C 5.86632700 -1.17607300 2.50251200

H 5.76079900 -1.88727700 3.32473800

H 5.58170400 -1.65235700 1.56499900

H 6.89983800 -0.82915100 2.43891200

O 4.96148400 -0.05455600 2.67635900

H 5.17848200 0.41376300 3.49073800

C 5.44977000 0.77191000 -0.77886800

H 5.42239300 -0.32149600 -0.78429100

H 5.11726300 1.13632900 -1.75118600

H 6.47265700 1.11956400 -0.60462800

O 4.54235300 1.29999700 0.20120200

H 4.79560200 0.97420100 1.07984900

C -7.52670900 -2.58366100 -0.13060700

H -7.06618800 -3.35542100 -0.74818600

H -8.60724800 -2.59844100 -0.29775500

H -7.32006400 -2.79557300 0.92376400

O -6.97443600 -1.32424400 -0.52951400

H -7.32490100 -0.59836000 0.04190400

C -8.14967900 1.92317100 0.86792700

H -9.20109000 1.64294800 0.93442000

H -7.95971200 2.35409700 -0.12152400

H -7.93826600 2.67397800 1.63595700

O -7.37881400 0.73820700 1.08375600

H -6.42830400 0.93911300 1.00962200

C 3.77921800 -3.72692000 -0.07901500

H 2.76289100 -4.09995900 -0.24079300

H 4.43509500 -4.14599200 -0.84159700

H 4.13208600 -4.05347800 0.90439600

O 3.83991100 -2.29750000 -0.20153000

H 3.28480000 -1.88682800 0.48871400

Figure S4. Lowest Energy O-protonated Structures

O-protonated (4-ABA)•(MeOH)•H+

Electronic: -592.493817hartree

ZPE corrected: −592.294992hartree

Enthalpy (298 K): −592.281049hartree

Gibbs (298 K): −592.335243hartree

XYZ Atomic Coordinates:

C 3.28173800 -0.00000400 0.10632300

C 2.56181300 -1.22515800 0.05327200

C 1.19657600 -1.22317600 -0.04639300

C 0.47684600 0.00000300 -0.09835200

C 1.19658100 1.22317900 -0.04638700

C 2.56181900 1.22515400 0.05327800

H 3.10341200 -2.16310500 0.09254700

H 0.65880900 -2.16175200 -0.08630800

H 0.65881900 2.16175800 -0.08629700

H 3.10342200 2.16309900 0.09255700

C -0.92883400 0.00000600 -0.20082500

O -1.58205600 1.13523500 -0.24742500

O -1.58206200 -1.13521800 -0.24742900

H -2.55554600 -0.99370700 -0.32096700

N 4.62471400 -0.00000700 0.20561500

H 5.14868000 0.85985000 0.24452300

H 5.14867600 -0.85986600 0.24451900

H -2.55554000 0.99373000 -0.32096000

C -4.93406400 -0.00001300 0.78016200

H -5.55340300 -0.89745100 0.77094400

H -4.29957700 -0.00003100 1.66473500

H -5.55339500 0.89743100 0.77097300

O -4.03578100 0.00000100 -0.37083000

H -4.55301000 0.00001000 -1.18656200

O-protonated (4-ABA)•(MeOH)2•H+

Electronic: − 708.2875935hartree

ZPE corrected: −708.036673hartree

Enthalpy (298 K): −708.018193hartree

Gibbs (298 K): −708.084525hartree

XYZ Atomic Coordinates:

C -4.02654500 -0.01819400 0.06079300

C -3.28990900 -1.23022600 0.00383500

C -1.91964800 -1.20890200 -0.05431900

C -1.21454100 0.01939600 -0.05887100

C -1.95048500 1.22838000 -0.00252500

C -3.32062500 1.21318900 0.05556400

H -3.81954100 -2.17596000 0.00564400

H -1.37013700 -2.14020100 -0.09890100

H -1.42217700 2.17301400 -0.00343300

H -3.87344900 2.14448100 0.10019900

C 0.20610900 0.04671300 -0.11628300

O 0.82432800 1.17771200 -0.17830800

O 0.85003100 -1.09458700 -0.10631900

H 1.82950400 -1.06289800 -0.26557700

N -5.37598600 -0.03627600 0.11901700

H -5.91037300 0.81626900 0.16091600

H -5.88924200 -0.90266200 0.12635900

H 1.84779300 1.16533600 -0.06923600

C 4.07772500 2.45625400 0.10204600

H 3.45445900 3.22948000 0.54769200

H 4.99454700 2.35434400 0.68512500

H 4.31205400 2.72495800 -0.93045100

O 3.31878000 1.22734200 0.15637400

H 3.80516500 0.47242100 -0.20908100

C 4.04291700 -2.25859700 0.54093600

H 5.12272900 -2.35242900 0.41710700

H 3.82485600 -1.75267800 1.47975400

H 3.57084900 -3.24245300 0.53363200

O 3.48729900 -1.41944400 -0.51270300

H 3.68138300 -1.81336300 -1.37226400

O-protonated (4-ABA)•(MeOH)3•H+ (Isomer 1)

Electronic: − 824.079931hartree

ZPE corrected: −823.775882hartree

Enthalpy (298 K): −823.752735hartree

Gibbs (298 K): −823.832086hartree

XYZ Atomic Coordinates:

C -4.73568800 -0.00409400 0.11166400

C -4.04116400 1.07638300 -0.48973000

C -2.66940000 1.07698400 -0.54468600

C -1.92345700 0.00244700 -0.00599100

C -2.61673500 -1.07540000 0.59297800

C -3.98828800 -1.08112300 0.65290900

H -4.60250800 1.90534800 -0.90541400

H -2.14916800 1.90734500 -1.00443100

H -2.05616200 -1.90326800 1.00762000

H -4.50918500 -1.91269000 1.11360000

C -0.49817300 0.00517600 -0.06711000

O 0.16241100 -0.94853900 0.51303100

O 0.10660900 0.96124600 -0.70120200

H 1.09655800 1.07252400 -0.49072900

N -6.08760200 -0.00737300 0.16830200

H -6.59214200 -0.76738800 0.59408700

H -6.62980900 0.74976000 -0.21410400

H 1.12880200 -1.05907800 0.21406100

C 5.56393600 -0.03795500 0.97057600

H 6.19607700 0.84876100 1.04787900

H 4.85054500 -0.04978200 1.79306200

H 6.17542000 -0.94161700 1.00472600

O 4.77789700 0.00057500 -0.24920300

H 5.36425800 0.02214300 -1.01473900

C 2.59139400 -2.92805300 -0.74636600

H 3.15765300 -3.47176500 0.01416100

H 1.58592300 -3.34283300 -0.80659100

H 3.07651300 -3.03026000 -1.72000900

O 2.45499600 -1.53865200 -0.39294200

H 3.32546600 -1.10679200 -0.33107100

C 2.65374000 2.95137700 0.26033100

H 3.31349600 3.09589000 1.11915900

H 3.05758400 3.46790200 -0.61412100

H 1.67203600 3.36035800 0.49588300

O 2.47409200 1.54697600 -0.00563300

H 3.32683100 1.11975000 -0.20101700

O-protonated (4-ABA)•(MeOH)3•H+ (Isomer 2)

Electronic: − 824.0727336hartree

ZPE corrected: −823.768603hartree

Enthalpy (298 K): −823.745233hartree

Gibbs (298 K): −823.825698hartree

XYZ Atomic Coordinates:

C 2.91183200 -1.06410200 -0.02894400

C 1.96014500 -2.05950700 -0.38747200

C 0.62289100 -1.76496500 -0.41883600

C 0.15825500 -0.46382100 -0.09569000

C 1.10843100 0.52889700 0.26289800

C 2.44655300 0.24220300 0.29728400

H 2.30395800 -3.05729200 -0.63558900

H -0.09012500 -2.53209500 -0.69213200

H 0.76425900 1.52515400 0.50961800

H 3.17269000 0.99779500 0.57207700

C -1.22248600 -0.15501100 -0.12994900

O -1.63383700 1.01840500 0.23369800

O -2.06389500 -1.08137200 -0.53052700

H -3.02690100 -0.88611000 -0.41120600

N 4.22716800 -1.33775600 0.00374600

H 4.90118500 -0.61677200 0.26103500

H 4.56561600 -2.25868200 -0.22378500

H -2.60472900 1.25196500 0.01641700

C 6.37807600 1.77298300 -0.37298000

H 7.42147000 1.48942500 -0.53812500

H 5.80910500 1.57563900 -1.28137000

H 6.31768800 2.84007200 -0.14150700

O 5.77646500 0.98198200 0.66769200

H 6.24969200 1.12308700 1.49404900

C -4.55920200 2.99153300 -0.16477100

H -4.98738400 3.09844800 0.83478600

H -3.73594800 3.69403300 -0.28320100

H -5.31619900 3.19605700 -0.92427300

O -4.00987200 1.67087300 -0.35297700

H -4.67756300 0.97214200 -0.27894100

C -5.17492400 -1.60001800 1.03996000

H -6.25743900 -1.52278400 1.15309100

H -4.86407800 -2.64618800 1.06000900

H -4.68560300 -1.05791900 1.84763500

O -4.74945200 -0.96447800 -0.19652300

H -5.18257900 -1.39411300 -0.94470100

O-protonated (4-ABA)•(MeOH)4•H+ (Isomer 1)

Electronic: − 939.8697949hartree

ZPE corrected: −939.513287hartree

Enthalpy (298 K): −939.485246hartree

Gibbs (298 K): −939.580072hartree

XYZ Atomic Coordinates:

C 5.54642900 -0.19546000 -0.26335100

C 4.92680300 1.00672700 0.16126300

C 3.55958300 1.08496300 0.26892200

C 2.74533500 -0.02900600 -0.03834400

C 3.36373900 -1.22815100 -0.46015000

C 4.73024200 -1.31254000 -0.57214300

H 5.54116600 1.86756700 0.39940900

H 3.09680700 2.00819400 0.59305000

H 2.74968400 -2.08755400 -0.69656000

H 5.19321800 -2.23768800 -0.89610600

C 1.32255200 0.05447000 0.07703100

O 0.60046900 -0.95492400 -0.29379900

O 0.79099400 1.13621000 0.54978400

H -0.20792800 1.26738500 0.36189200

N 6.89415100 -0.27522400 -0.37222400

H 7.34571700 -1.12266000 -0.67393200

H 7.48444600 0.51010900 -0.15333100

H -0.36043100 -0.97119100 0.06021800

C -6.17052900 -1.37425900 -1.69124500

H -5.92964700 -1.56914000 -2.73940500

H -5.63289600 -2.08494200 -1.06437800

H -7.24409400 -1.49367300 -1.52526700

O -5.72985100 -0.06166200 -1.29379300

H -6.17654100 0.61134800 -1.81693000

C -1.72615500 3.06194200 -0.60783600

H -2.34030300 3.05849300 -1.51193100

H -2.17442200 3.71577400 0.14515800

H -0.73318300 3.43513700 -0.85698900

O -1.56635500 1.72655800 -0.10197700

H -2.43170600 1.32933500 0.12997100

C -1.88636400 -2.55026600 1.34919400

H -2.37682100 -2.45398800 2.32120100

H -2.48904800 -3.17957100 0.68849700

H -0.91128500 -3.01552900 1.49082400

O -1.66250200 -1.25601400 0.76704700

H -2.50650200 -0.77383400 0.64067800

C -4.49526000 0.65673700 1.79540800

H -5.06778600 1.58425500 1.72026800

H -5.16107300 -0.16168200 2.07956300

H -3.72115300 0.77259600 2.55380000

O -3.83233700 0.36408800 0.54805900

H -4.50685300 0.23283600 -0.15920200

O-protonated (4-ABA)•(MeOH)4•H+ (Isomer 2)

Electronic: − 939.8644336hartree

ZPE corrected: −939.507034hartree

Enthalpy (298 K): −939.479042hartree

Gibbs (298 K): −939.572181hartree

XYZ Atomic Coordinates:

C 3.69028200 -1.00995800 -0.28583900

C 2.75106600 -1.94168400 -0.80635500

C 1.40463000 -1.70323900 -0.70587700

C 0.92093200 -0.52436800 -0.08597800

C 1.85816200 0.40590400 0.43141100

C 3.20559100 0.17398300 0.33786700

H 3.10985100 -2.84743500 -1.28220900

H 0.69832500 -2.42091000 -1.10317900

H 1.49855100 1.30928200 0.90740000

H 3.92315800 0.88172700 0.73534100

C -0.47446400 -0.28263300 0.01784100

O -0.89628500 0.76215000 0.66850800

O -1.31108800 -1.10906700 -0.53929400

H -2.26122400 -1.05437200 -0.19229900

N 5.01538800 -1.23049700 -0.37635200

H 5.67992500 -0.56065300 0.00815500

H 5.36739700 -2.06820900 -0.81005900

H -1.85212800 1.03134000 0.47040000

C 7.07781100 1.96093300 -0.14007300

H 8.12704600 1.75933200 -0.37489200

H 6.49630700 1.92762500 -1.06129600

H 6.98387600 2.95661400 0.30275400

O 6.52931100 0.95325500 0.72724000

H 7.02048300 0.93798700 1.55491500

C -3.95265900 -2.61550300 0.96790200

H -4.42119900 -2.58077500 1.95455800

H -4.61226300 -3.12121900 0.25771900

H -3.01696500 -3.16869800 1.04051300

O -3.62523200 -1.28922400 0.51574900

H -4.42378800 -0.73754800 0.44568300

C -3.10712500 3.10108200 -0.41983400

H -3.73532700 3.27804400 -1.29654400

H -3.41958100 3.75150600 0.40137500

H -2.07202600 3.32339500 -0.67664100

O -3.15815700 1.71613900 -0.03242800

H -4.06701700 1.45359700 0.19457600

C -6.48570900 0.60736700 -0.89852400

H -7.23938300 -0.18223400 -0.87745400

H -6.96285400 1.58077900 -1.02872100

H -5.79437800 0.42799000 -1.72043600

O -5.68981000 0.58673200 0.31406700

H -6.25552400 0.74513600 1.07883900

O-protonated (4-ABA)•(MeOH)5•H+ (Isomer 1)

Electronic: − 1055.6538004hartree

ZPE corrected: −1055.243819hartree

Enthalpy (298 K): −1055.210979hartree

Gibbs (298 K): −1055.319567hartree

XYZ Atomic Coordinates:

C -4.62536400 0.80332600 -0.25018500

C -3.80835400 1.96269700 -0.33529900

C -2.44096700 1.85546600 -0.30943200

C -1.81483100 0.59012900 -0.20049200

C -2.62969200 -0.56626900 -0.11776100

C -3.99728500 -0.46822400 -0.14008000

H -4.27650300 2.93709800 -0.41921400

H -1.82854000 2.74577200 -0.37359200

H -2.16023700 -1.53843700 -0.03723000

H -4.62103100 -1.35218500 -0.08158100

C -0.39584100 0.48346600 -0.17778400

O 0.15188300 -0.67935600 0.01215100

O 0.32583200 1.54979900 -0.34790300

H 1.29571900 1.47758900 -0.04050400

N -5.96992300 0.89352900 -0.27122500

H -6.54670200 0.05694600 -0.20467600

H -6.42222500 1.78863600 -0.35853100

H 1.12751900 -0.75192700 -0.26768100

C 6.93236100 -2.33161700 1.23313300

H 6.59086400 -2.82947200 2.14444300

H 6.39533000 -2.74389500 0.37943300

H 8.00334000 -2.49899300 1.09402900

O 6.63096200 -0.92374200 1.26601000

H 7.08719300 -0.50357700 2.00183400

C 2.90424100 2.69333500 1.52780500

H 3.44497400 2.36763600 2.42021200

H 3.47283600 3.47196200 1.01160200

H 1.93897200 3.09945300 1.82914600

O 2.64624100 1.57873100 0.65967000

H 3.48139300 1.16852400 0.35366700

C 2.57431700 -2.19105200 -1.83446600

H 3.10514200 -1.91557900 -2.74981400

H 3.08542100 -3.02550300 -1.34576300

H 1.56185800 -2.49956800 -2.09395200

O 2.46477200 -1.06453200 -0.95223600

H 3.34794300 -0.71954900 -0.70780400

C 5.49477400 0.77670800 -1.44479000

H 6.16811900 1.57243400 -1.11720900

H 6.06691800 0.00802600 -1.97008600

H 4.74669800 1.19334500 -2.11910700

O 4.78987100 0.20999800 -0.32176900

H 5.43802800 -0.18758500 0.30503100

C -7.59199500 -2.07591200 1.42036200

H -6.98002100 -1.49039400 2.10640900

H -7.39731700 -3.13863500 1.59109400

H -8.64704700 -1.85910200 1.61211400

O -7.20646700 -1.68368400 0.09201400

H -7.72211200 -2.17775700 -0.55325900

O-protonated (4-ABA)•(MeOH)5•H+ (Isomer 2)

Electronic: − 1055.6521608hartree

ZPE corrected: −1055.241916hartree

Enthalpy (298 K): −1055.209668hartree

Gibbs (298 K): −1055.313248hartree

XYZ Atomic Coordinates:

C 4.20124500 -0.92118000 0.01537700

C 3.38505300 -2.07619800 0.14816700

C 2.02310100 -1.98762100 0.00608900

C 1.40211400 -0.74699500 -0.27437800

C 2.21596500 0.40502900 -0.40582900

C 3.57824200 0.32604300 -0.26510100

H 3.84891500 -3.03236700 0.36334300

H 1.41086900 -2.87442000 0.10860700

H 1.75139100 1.35775600 -0.62581200

H 4.20195200 1.20555300 -0.37200300

C -0.01262400 -0.66518800 -0.42859300

O -0.55853800 0.50413800 -0.59991000

O -0.71941900 -1.74799400 -0.40014200

H -1.74695800 -1.65949600 -0.24623400

N 5.54065900 -0.99267200 0.15241400

H 6.11828400 -0.16156900 0.04125900

H 5.99062700 -1.87485000 0.33305000

H -1.51599400 0.50837100 -0.93945500

C -4.50021200 0.24020400 2.90336600

H -4.18479200 1.14641500 3.42855400

H -5.58678200 0.13275000 2.97609900

H -4.02813300 -0.61945800 3.37864900

O -4.06595700 0.26069900 1.53664800

H -4.44338000 1.02018900 1.06266600

C 7.16395000 2.32361200 1.06570600

H 6.54056200 1.94623800 1.87620100

H 8.21518400 2.15863100 1.32000400

H 6.97812500 3.39478800 0.94499500

O 6.78647800 1.59431900 -0.11435000

H 7.31696500 1.89129400 -0.86057300

C -3.37775000 -0.13644300 -2.66660100

H -3.93862400 0.44950200 -3.39869200

H -2.51028600 -0.57452000 -3.15992100

H -3.99587400 -0.93656100 -2.25459000

O -2.88193800 0.71221900 -1.61651900

H -3.60246400 1.21804200 -1.20156400

C -4.03882500 3.59588100 0.02175300

H -4.57709100 4.17845100 0.77219100

H -3.04948700 3.34230000 0.39949000

H -3.93843300 4.16912000 -0.90213500

O -4.71315500 2.33652800 -0.22854900

H -5.60518100 2.50632600 -0.55258900

C -3.58653100 -3.02598800 0.62020800

H -4.67683100 -3.07074300 0.66926600

H -3.22811400 -3.81095500 -0.04488700

H -3.16493800 -3.17921200 1.61806400

O -3.16863700 -1.76575500 0.06547500

H -3.51715700 -1.02305500 0.61690600

O-protonated (4-ABA)•(MeOH)6•H+ (Isomer 1)

Electronic: − 1171.4405398hartree

ZPE corrected: −1170.977918hartree

Enthalpy (298 K): −1170.940791hartree

Gibbs (298 K): −1171.060473hartree

XYZ Atomic Coordinates:

C -4.72017800 1.22542300 -0.37014600

C -4.48937500 -0.14756500 -0.08474000

C -3.21426600 -0.65506800 -0.09921300

C -2.10470800 0.17186900 -0.39742400

C -2.33468000 1.53831300 -0.67943100

C -3.60702200 2.05517600 -0.66710800

H -5.33884400 -0.78162100 0.13960200

H -3.04691800 -1.70199700 0.11986300

H -1.49446000 2.18028300 -0.91096800

H -3.77080000 3.10409200 -0.88830600

C -0.78273500 -0.37106500 -0.42095700

O 0.21757200 0.44416000 -0.61784900

O -0.61106600 -1.63398600 -0.25388500

H 0.36433000 -1.99873900 -0.03498300

N -5.97640800 1.71884900 -0.35411400

H -6.14921700 2.68754800 -0.56529400

H -6.76767500 1.11383000 -0.14542400

H 1.10672600 0.02602900 -0.87133100

C 5.97202200 -0.20560700 -0.76743300

H 6.25059100 0.28343600 -1.70446500

H 6.79763600 -0.12590300 -0.05597400

H 5.76480700 -1.25872300 -0.95818500

O 4.77075300 0.37495100 -0.22389900

H 4.93517900 1.32228700 -0.01203600

C 2.15289800 -3.51841600 -0.62758800

H 1.36841100 -4.14634500 -1.04946400

H 2.62329000 -2.93215700 -1.42084700

H 2.89337100 -4.15634500 -0.14034900

O 1.53902100 -2.65428500 0.34131200

H 2.22633400 -2.10460500 0.79531400

C -8.27169500 -0.40115200 1.80366800

H -8.36629900 -1.44647000 2.11190700

H -7.47366900 0.06572000 2.38092600

H -9.20907100 0.12732600 2.00161000

O -7.89048200 -0.29860500 0.42171800

H -8.56555600 -0.70492600 -0.13092300

C 3.82716300 -1.37887200 2.89729000

H 3.84687200 -0.43310600 3.44782400

H 3.12746200 -2.05431600 3.38919600

H 4.82369700 -1.83186100 2.91123800

O 3.36040600 -1.18480900 1.55789300

H 3.95238000 -0.59209300 1.05828800

C 2.57404300 -0.10470400 -2.92528900

H 2.63626600 0.96883600 -3.12660900

H 3.44627000 -0.60950700 -3.34914200

H 1.67498500 -0.50251600 -3.39568500

O 2.47481700 -0.36871800 -1.51590400

H 3.28078900 -0.03833900 -1.06330700

C 5.72263300 3.29061500 1.77240400

H 5.85275500 2.36464700 2.33179600

H 4.92759300 3.87984700 2.23708000

H 6.66122700 3.85030000 1.78882100

O 5.37187700 2.91178600 0.42816300

H 5.24861300 3.69580000 -0.11597400

O-protonated (4-ABA)•(MeOH)6•H+ (Isomer 2)

Electronic: − 1171.4338025hartree

ZPE corrected: −1170.970567hartree

Enthalpy (298 K): −1170.933155hartree

Gibbs (298 K): −1171.05251hartree

XYZ Atomic Coordinates:

C -3.72012900 0.07455900 0.05667700

C -3.13936600 -1.14655200 -0.39291700

C -1.78080400 -1.26117500 -0.52756900

C -0.92232500 -0.17233900 -0.22630800

C -1.50137200 1.04319700 0.22038300

C -2.85884700 1.16876500 0.36012600

H -3.79524800 -1.97679100 -0.62650600

H -1.34777700 -2.19355000 -0.86733300

H -0.85598300 1.88115800 0.45165500

H -3.30121500 2.09628400 0.70403200

C 0.48363000 -0.30399400 -0.37285300

O 1.25191300 0.69017000 0.00193900

O 0.98280400 -1.38673000 -0.86996800

H 2.00279600 -1.56807300 -0.71462800

N -5.05107000 0.19143800 0.19187900

H -5.45367100 1.06938700 0.50730100

H -5.65347400 -0.59816100 -0.02356200

H 2.19565000 0.67306700 -0.34735300

C 6.95534000 1.77396100 0.41183700

H 7.11784700 2.67127300 -0.18932800

H 7.66676200 1.74245900 1.23963300

H 7.08635000 0.88923500 -0.20931100

O 5.59326200 1.72576100 0.90440600

H 5.43130600 2.47669300 1.48700000

C 4.15996500 -2.19406200 -1.69777900

H 3.55449600 -2.71574400 -2.43877100

H 4.47037200 -1.22354800 -2.09390500

H 5.03774400 -2.80150200 -1.46617600

O 3.35249100 -2.02660300 -0.52312100

H 3.87950100 -1.59190700 0.18787000

C -6.55169900 -3.24393600 0.75218700

H -6.34112600 -4.28402200 0.48570900

H -5.85659300 -2.93258600 1.53203400

H -7.57355600 -3.16252700 1.13529800

O -6.33445200 -2.36517200 -0.36297200

H -6.92712400 -2.60387400 -1.08250400

C 5.05657800 -1.61527500 2.66492100

H 4.50112700 -1.14914500 3.48440000

H 4.71056900 -2.64134900 2.54347500

H 6.12401300 -1.62908300 2.90455000

O 4.81466700 -0.94165100 1.42166300

H 5.10416800 -0.01706600 1.46186300

C 3.63483300 1.83049400 -2.13503700

H 3.35857800 2.85887800 -1.88457500

H 4.61423100 1.81866900 -2.62067400

H 2.89617800 1.42219800 -2.82433600

O 3.63830400 0.98846900 -0.96886300

H 4.30014000 1.31191000 -0.33004100

C -6.05600600 3.81413200 -0.16485700

H -5.56722900 3.40152000 -1.04756200

H -5.66366600 4.81878100 0.01952400

H -7.13321400 3.86886300 -0.34990100

O -5.75113400 2.92718000 0.92284600

H -6.16608900 3.25042900 1.72864600

O-protonated (4-ABA)•(MeOH)7•H+ (Isomer 1)

Electronic: − 1287.2246701hartree

ZPE corrected: −1286.707151hartree

Enthalpy (298 K): −1286.665999hartree

Gibbs (298 K): −1286.791723hartree

XYZ Atomic Coordinates:

C 3.99993700 0.93280600 -0.07999500

C 3.65039000 -0.34127500 -0.60232700

C 2.37149200 -0.58770800 -1.03519300

C 1.37014900 0.41231300 -0.97557700

C 1.71809700 1.67785500 -0.45213800

C 2.99575900 1.93269400 -0.01238900

H 4.41436300 -1.10762400 -0.65919600

H 2.11857700 -1.56155300 -1.43414200

H 0.98129600 2.46663800 -0.37595800

H 3.24510600 2.91037000 0.38502000

C 0.04485500 0.10325200 -1.42414800

O -0.96177200 0.92607100 -1.43066700

O -0.20177800 -1.07240500 -1.88770800

H -1.21567300 -1.20371400 -2.07835100

N 5.25888900 1.17089600 0.34496600

H 5.52427700 2.08635800 0.66860100

H 5.98234300 0.46291500 0.23523900

H -0.88147600 1.81913200 -0.95690000

C -3.15157800 -2.75307900 -2.32933600

H -2.59717200 -3.24917700 -3.12505700

H -2.98714200 -3.27559700 -1.38345700

H -4.21391900 -2.75873700 -2.58569400

O -2.66675100 -1.39928700 -2.25569000

H -3.15063700 -0.91041600 -1.55892300

C 7.39424700 -1.96009400 1.00911400

H 8.37808000 -1.66652600 1.38700900

H 6.65888300 -1.83666600 1.80409000

H 7.41485300 -3.01078700 0.70566100

O 6.97241400 -1.11438400 -0.07420700

H 7.59582900 -1.19105500 -0.80367800

C -5.42245400 0.08792300 -0.28311500

H -5.51697400 0.99118100 -0.89192700

H -5.91161000 -0.73829300 -0.79849300

H -5.91083300 0.24265300 0.68314700

O -4.04048200 -0.27142000 -0.10946200

H -3.57123400 0.43868500 0.38099300

C -1.84326400 4.20954100 -0.78395900

H -2.02941400 5.01558200 -0.07038600

H -1.17125600 4.57224300 -1.56102700

H -2.78570500 3.89614400 -1.24321100

O -1.18809200 3.10620500 -0.13346500

H -1.76604500 2.71528800 0.55748600

C -3.23825700 -3.28872500 2.01514500

H -4.04515000 -3.89330000 1.58988600

H -2.44028700 -3.95482400 2.34260100

H -3.61809900 -2.73740800 2.88231100

O -2.68091000 -2.40813300 1.03176500

H -3.36416100 -1.79669900 0.70063000

C -3.10002200 1.65710500 2.80180900

H -2.34804500 2.07977700 3.47356300

H -3.48411500 0.72583300 3.22872000

H -3.92114400 2.36599800 2.69611800

O -2.54840200 1.42825800 1.49305000

H -1.81776600 0.75503100 1.55955400

C 0.45131700 -0.80393400 2.06731300

H 0.28836300 -1.14053500 3.09628000

H 1.03449600 0.11683000 2.07785700

H 1.01578800 -1.56260700 1.51849400

O -0.78707700 -0.52020200 1.40684600

H -1.33783600 -1.33109000 1.32345900

O-protonated (4-ABA)•(MeOH)7•H+ (Isomer 2)

Electronic: − 1287.2293911hartree

ZPE corrected: −1286.711282hartree

Enthalpy (298 K): −1286.67055hartree

Gibbs (298 K): −1286.793292hartree

XYZ Atomic Coordinates:

C 3.87278700 0.79682400 -0.42438800

C 3.49457500 -0.56292700 -0.58770600

C 2.20374300 -0.88982200 -0.91901900

C 1.21524000 0.10894400 -1.10340500

C 1.59435500 1.46102400 -0.94337000

C 2.88498000 1.79765300 -0.60925300

H 4.24622600 -1.33196800 -0.45431100

H 1.93092100 -1.92960100 -1.04325200

H 0.87390400 2.25600800 -1.08018800

H 3.15773300 2.84102000 -0.49501100

C -0.12344800 -0.28551500 -1.43080900

O -1.13266400 0.51124000 -1.60292700

O -0.36850000 -1.54213100 -1.59823600

H -1.36752700 -1.73928300 -1.75026000

N 5.14313000 1.11438000 -0.09589700

H 5.42741700 2.07764900 -0.02875900

H 5.85394400 0.38918100 -0.02376000

H -1.05402700 1.49634600 -1.32462600

C -3.07042200 -3.54220000 -1.54402300

H -2.32591100 -4.16245100 -2.04161600

H -2.99414300 -3.67134100 -0.46117600

H -4.06311700 -3.83691800 -1.89322600

O -2.79697200 -2.17660500 -1.91471300

H -3.43735600 -1.58671400 -1.47711100

C 7.23948500 -1.76475600 1.35424000

H 8.23265900 -1.39958200 1.63219000

H 6.51631700 -1.41963700 2.09308700

H 7.23968000 -2.85856000 1.34268900

O 6.81728100 -1.23139900 0.08789600

H 7.43100500 -1.50991400 -0.59940900

C -4.29241300 0.80325100 -0.32599000

H -4.91331200 1.28855700 0.42965800

H -3.24928700 0.87078500 -0.03000200

H -4.42688000 1.28478500 -1.29708500

O -4.60504000 -0.60966400 -0.41507100

H -5.53748600 -0.72070400 -0.63285200

C -2.12896600 3.81803000 -1.47522800

H -1.96434100 4.83826300 -1.12046700

H -1.92981400 3.77878500 -2.54609000

H -3.17035200 3.53442800 -1.29295000

O -1.22164800 2.91366100 -0.83000300

H -1.41768100 2.84172200 0.14291700

C -3.62615700 -2.41488400 2.75135000

H -4.37607100 -3.19204100 2.57604200

H -2.81009600 -2.84403200 3.33247100

H -4.07613800 -1.59632600 3.32262600

O -3.06680600 -1.95008700 1.51476800

H -3.76430700 -1.56144200 0.96032200

C -1.45418200 2.98636700 2.87747800

H -0.37386400 3.04569200 3.04837200

H -1.92729800 2.48849700 3.72938600

H -1.85426800 3.99753200 2.79925100

O -1.75624200 2.30351600 1.65639800

H -1.43211600 1.37285100 1.69796800

C 0.23092200 -0.80092900 2.05775600

H 0.11516400 -0.94455200 3.13752400

H 1.04757300 -0.10257700 1.87428200

H 0.48356900 -1.75756200 1.59081600

O -0.95075100 -0.24457500 1.47241500

H -1.68487700 -0.89557200 1.52382200

O-protonated (4-ABA)•(MeOH)7•H+ (Isomer 3)

Electronic: − 1287.2246701hartree

ZPE corrected: −1286.707151hartree

Enthalpy (298 K): −1286.665999hartree

Gibbs (298 K): −1286.791723hartree

XYZ Atomic Coordinates:

C -4.20356300 0.03422700 -0.33698000

C -3.42118600 1.22563200 -0.33388000

C -2.05687900 1.16011500 -0.43981400

C -1.39186900 -0.08870400 -0.55005000

C -2.17182800 -1.27421700 -0.55217300

C -3.53685900 -1.22054600 -0.44931600

H -3.93038500 2.17912200 -0.25715300

H -1.47063300 2.07039600 -0.44673700

H -1.67316300 -2.23147800 -0.63754100

H -4.13345800 -2.12512000 -0.45531000

C 0.02045500 -0.14946800 -0.66664900

O 0.60031900 -1.29522200 -0.88162100

O 0.72141200 0.94306300 -0.55333100

H 1.66165900 0.92164200 -0.97536500

N -5.54088600 0.09258600 -0.23414000

H -6.08876900 -0.76310200 -0.25601800

H -6.00505800 0.99397500 -0.16432500

H 1.59524500 -1.33371600 -0.62510200

C 3.55304200 -2.79443700 0.10293300

H 3.17254300 -3.21526000 1.03831400

H 3.25039400 -3.43570900 -0.72490600

H 4.64371800 -2.74032000 0.13524900

O 3.00970800 -1.48757500 -0.14102100

H 3.20892800 -0.88570600 0.61877000

C 5.93887600 2.57725300 -0.22732800

H 5.23785200 3.40749900 -0.30665900

H 6.57312300 2.72514200 0.65099000

H 6.55929800 2.54850200 -1.12716300

O 5.16304500 1.37206900 -0.10033100

H 5.75882100 0.59266600 -0.02530100

C 6.65743300 -1.23167000 1.77068600

H 6.76544100 -2.31328000 1.88680100

H 7.48211600 -0.72233800 2.27687800

H 5.71136300 -0.91486000 2.20779900

O 6.59982600 -0.87223300 0.37329800

H 7.41129600 -1.14527400 -0.06703500

C -7.00136400 -3.20966400 1.04585900

H -8.05699300 -3.07673800 1.30210900

H -6.75700000 -4.27615800 1.03831700

H -6.38995400 -2.71393000 1.79997200

O -6.68113400 -2.59192700 -0.21039200

H -7.19695600 -3.00150100 -0.91205300

C 2.46043700 0.89043900 2.51736400

H 2.84873700 1.60704100 3.24618900

H 1.76769600 1.39211000 1.83494400

H 1.92715600 0.10339600 3.05035700

O 3.53434000 0.26064200 1.79965700

H 4.05577800 0.92242500 1.30847500

C -6.66889000 3.35260000 1.40970700

H -6.09813000 2.72101700 2.09061600

H -7.72956400 3.28765700 1.67134400

H -6.32715800 4.38650400 1.51680800

O -6.42016400 2.85499000 0.08578700

H -6.90316100 3.38654200 -0.55475800

C 3.22176200 0.28907800 -2.85158400

H 3.99736700 0.75252200 -3.46603100

H 2.29787500 0.24493200 -3.42838300

H 3.52089700 -0.72160100 -2.56310800

O 2.96328400 1.09152600 -1.68849800

H 3.77678900 1.15839200 -1.14301500

O-protonated (4-ABA)•(MeOH)8•H+ (Isomer 1)

Electronic: − 1403.0220619hartree

ZPE corrected: −1402.450063hartree

Enthalpy (298 K): −1402.405623hartree

Gibbs (298 K): −1402.538263hartree

XYZ Atomic Coordinates:

C -0.27225900 -2.48165100 0.73691200

C 0.95076200 -2.92327800 1.30792300

C 2.13482500 -2.30616300 0.98865200

C 2.16424400 -1.19648900 0.10890000

C 0.94128300 -0.74359400 -0.44164600

C -0.24561200 -1.36243900 -0.13810900

H 0.94585700 -3.76822700 1.98756300

H 3.06148100 -2.66573500 1.41726000

H 0.92601700 0.08923200 -1.13139700

H -1.17057400 -1.00129800 -0.56845800

C 3.41666400 -0.59316200 -0.23372300

O 3.55432900 0.53943200 -0.84116700

O 4.50943000 -1.22642200 0.06437100

H 5.33378200 -0.68857900 -0.17031400

N -1.44479100 -3.08961100 1.01999700

H -2.26068700 -2.89211700 0.43286300

H -1.44367300 -3.94525900 1.55251600

H 2.74413100 1.21843300 -0.79941800

C 7.96592200 -0.47696400 -0.48610000

H 8.72086600 0.28416900 -0.27849600

H 7.97183200 -1.21360500 0.31562600

H 8.17942900 -0.97270800 -1.43631600

O 6.64740500 0.11140800 -0.49107500

H 6.57596400 0.78305400 -1.17754700

C -3.84982400 -0.56655200 2.51046200

H -4.68368300 -1.26328900 2.42267400

H -2.92021100 -1.09960900 2.28533300

H -3.81794100 -0.18658100 3.53588000

O -4.08495400 0.49837400 1.57987700

H -3.33353000 1.12211100 1.58523500

C 0.90221200 1.11968700 2.60581600

H 0.53082500 0.12607600 2.33651400

H 1.98944500 1.08180600 2.67969000

H 0.49685800 1.41536600 3.57750800

O 0.57124300 2.08947500 1.60450300

H -0.40412700 2.14625200 1.49525500

C -1.50407700 1.43547700 -2.62213600

H -1.37990200 0.52994500 -3.22504400

H -2.07151900 2.17493700 -3.19608200

H -0.51836000 1.84287100 -2.39213200

O -2.13603800 1.13593600 -1.37409500

H -3.03819400 0.77169200 -1.49346900

C 2.28466500 3.58767400 -0.86782700

H 2.99821900 3.84588000 -0.08060300

H 2.78054500 3.62575400 -1.83746700

H 1.45961200 4.30289100 -0.86022500

O 1.77693000 2.25198000 -0.68934900

H 1.30832700 2.18350500 0.19506800

C -3.01083500 -2.88764600 -2.25399000

H -2.40738200 -3.79092600 -2.15416800

H -2.41557100 -2.12887800 -2.77718200

H -3.89523700 -3.12604000 -2.85379000

O -3.36949000 -2.46134900 -0.93991200

H -3.89487000 -1.63961000 -0.99791200

C -5.90905500 0.29664900 -1.44651000

H -6.64395500 -0.33300000 -0.93765400

H -5.93677100 0.08176600 -2.51481700

H -6.16013500 1.34905300 -1.28659100

O -4.58081700 0.01006400 -0.97995700

H -4.51011500 0.19240900 -0.00682300

C -2.56120300 3.64555200 0.99733700

H -2.57413600 3.99727300 2.02835600

H -1.91698000 4.30096200 0.40409500

H -3.57851200 3.67476800 0.59726200

O -2.05542900 2.29777300 1.00582400

H -2.04072200 1.94655200 0.07929900

O-protonated (4-ABA)•(MeOH)8•H+ (Isomer 2)

Electronic: − 1403.0205631hartree

ZPE corrected: −1402.450939hartree

Enthalpy (298 K): −1402.40599hartree

Gibbs (298 K): −1402.540439hartree

XYZ Atomic Coordinates:

C 3.30447100 -1.51248900 0.85024300

C 2.18445700 -1.99195800 1.56644900

C 0.90807400 -1.83030900 1.06768700

C 0.68609500 -1.16444200 -0.15022100

C 1.79988000 -0.69469700 -0.86800200

C 3.08284400 -0.86977900 -0.39082600

H 2.33637600 -2.49874000 2.51359400

H 0.06193600 -2.21257000 1.62332100

H 1.64752700 -0.21394300 -1.82746200

H 3.93965200 -0.53339900 -0.96321900

C -0.65826400 -0.94362300 -0.67386000

O -0.92514500 -0.17169000 -1.60486000

O -1.62618600 -1.63851300 -0.07727300

H -2.49689600 -1.35892900 -0.46214900

N 4.57080700 -1.64402100 1.33979900

H 5.35692500 -1.47332500 0.72024100

H 4.73125200 -2.24595600 2.13079100

H -0.18956500 1.23227200 -1.90114200

C 3.11447600 2.86714300 -0.80184000

H 3.50361700 1.85167400 -0.72594300

H 3.12726300 3.20375200 -1.83726300

H 3.70039700 3.54879800 -0.18688300

O 1.74207000 2.91130400 -0.33768200

H 1.59623100 2.40922300 0.60456700

C -0.95835700 3.04360400 -2.29620300

H -1.74702600 2.89981000 -1.55435100

H -0.58252500 4.06582800 -2.25387600

H -1.34187000 2.84491600 -3.29884300

O 0.15230400 2.16089000 -2.02458700

H 1.03340500 2.56116000 -1.07346800

C 6.26441000 -2.35592400 -1.81642400

H 6.43047600 -2.06225100 -2.85716800

H 6.96168800 -3.15425100 -1.54446200

H 5.24467800 -2.72755200 -1.71368100

O 6.37937500 -1.22933600 -0.93115200

H 7.26907200 -0.86717300 -0.98898600

C -4.18146700 2.35197200 0.66202000

H -4.80043800 1.71312700 1.30125400

H -3.80352700 3.18406300 1.25654200

H -4.79562600 2.75191800 -0.15090700

O -3.04821600 1.64160600 0.14831300

H -3.36238800 0.86003200 -0.34821100

C 1.65096200 2.47740600 2.99792100

H 1.61002300 1.79408200 3.84847500

H 2.65928700 2.88421600 2.92171500

H 0.93721900 3.29275500 3.14408500

O 1.37698100 1.75723300 1.78405400

H 0.44395000 1.40119700 1.80859200

C -5.89996900 -3.25390600 0.53729500

H -4.82620200 -3.41624100 0.62718600

H -6.30794700 -3.95711300 -0.19397300

H -6.36743300 -3.41663100 1.51180000

O -6.07315300 -1.89082700 0.10570600

H -7.00951700 -1.69160900 0.00744400

C -4.04775000 -0.72318100 -2.49791500

H -4.26959300 -1.73404300 -2.84980600

H -3.07556500 -0.41196200 -2.87579200

H -4.82183300 -0.03471600 -2.84721300

O -3.95807900 -0.69469200 -1.05817100

H -4.77489500 -1.07607800 -0.66501000

C -1.63213300 0.05442300 2.82958600

H -0.81511100 -0.25169900 3.48423800

H -2.41874000 0.51051100 3.43938500

H -2.02439700 -0.83032200 2.32066800

O -1.10289500 0.99060400 1.88842500

H -1.79834800 1.24925300 1.23965600

O-protonated (4-ABA)•(MeOH)8•H+ (Isomer 3)

Electronic: − 1403.0193645hartree

ZPE corrected: −1402.447372hartree

Enthalpy (298 K): −1402.402403hartree

Gibbs (298 K): −1402.536983hartree

XYZ Atomic Coordinates:

C 4.04432700 0.01423700 0.33699900

C 3.65033700 -1.33002900 0.59420200

C 2.34922400 -1.71969000 0.41389800

C 1.35784200 -0.79806300 -0.01515200

C 1.75286500 0.53925600 -0.27449200

C 3.05471500 0.93746000 -0.10677000

H 4.39982000 -2.03347900 0.93696500

H 2.06171100 -2.74447000 0.61144000

H 1.03058400 1.26368800 -0.62809000

H 3.35356200 1.95806600 -0.31504600

C 0.01501500 -1.24297700 -0.19448300

O -1.00896700 -0.46304100 -0.40681100

O -0.23944500 -2.50981600 -0.16569700

H -1.24835000 -2.72083300 -0.21447800

N 5.31983200 0.40050100 0.50208400

H 5.58984000 1.35819900 0.29682200

H 6.01785600 -0.27306700 0.80551600

H -0.90739000 0.52969100 -0.16650400

C -3.17095700 -3.85346100 -1.40358100

H -3.33717300 -3.18727800 -2.25651900

H -2.41582400 -4.59230200 -1.67054600

H -4.09988300 -4.37470600 -1.15765100

O -2.68387500 -3.13155300 -0.26437100

H -3.33384300 -2.44224100 -0.00075600

C -3.41471900 -0.06064700 -2.88425200

H -3.97233400 -0.80468800 -3.46158700

H -3.16727200 0.77158900 -3.54362300

H -2.49029800 -0.50302900 -2.50111200

O -4.21874500 0.45992500 -1.81795500

H -4.39969700 -0.24669800 -1.16605700

C 7.56123900 -2.63822400 0.12343100

H 7.50153500 -3.71618000 0.30080200

H 6.98845800 -2.39677100 -0.77212100

H 8.60470900 -2.34900200 -0.03468000

O 6.96588000 -1.89825500 1.20093600

H 7.44010300 -2.07988100 2.01835300

C -4.19552200 3.78557900 -0.66770900

H -3.80690300 4.13359900 -1.62858500

H -5.28362900 3.69811800 -0.72575500

H -3.93510200 4.50956100 0.10445900

O -3.60334500 2.52732700 -0.30230500

H -3.84502600 1.82520800 -0.96480100

C -5.87594600 -1.76426100 0.63841800

H -5.86424400 -2.28719800 1.59850300

H -6.60588700 -0.95083100 0.67089700

H -6.16314500 -2.46481200 -0.14558200

O -4.56700400 -1.26134600 0.31388600

H -4.31694400 -0.56225100 0.96921400

C -4.59428900 1.23958200 3.06888100

H -4.59226900 0.37812500 3.73662900

H -5.62894100 1.55182900 2.89331000

H -4.04768500 2.05611400 3.55098300

O -3.94981900 0.83955500 1.85278400

H -3.92684200 1.58285400 1.21775200

C 5.98562900 3.29025400 -1.80697100

H 5.62622800 2.39061400 -2.30687800

H 7.06788100 3.36647900 -1.95006400

H 5.49443700 4.16134000 -2.25090100

O 5.64469200 3.14978600 -0.41865700

H 5.94571800 3.92425300 0.06678400

C -0.77446400 2.22554800 1.63740100

H -1.48836900 1.67222500 2.25367900

H 0.23819200 1.88438500 1.85219600

H -0.84120000 3.29465000 1.85264100

O -1.01816900 1.98363100 0.23878700

H -1.92260700 2.29855500 0.00611900

Figure S5. Lowest Energy Solvent-bridged Structures

Bridged (4-ABA)•(MeOH)3•H+

Electronic: −824.0767461hartree

ZPE corrected: −823.772982hartree

Enthalpy (298 K): −823.750894hartree

Gibbs (298 K): −823.825128hartree

XYZ Atomic Coordinates:

C -1.44034100 -1.88496600 -0.51831400

C -0.75384300 -2.39924800 0.59123300

C 0.59738300 -2.13278700 0.76021300

C 1.27415500 -1.31741600 -0.15644900

C 0.59648500 -0.84786500 -1.29054500

C -0.74100900 -1.13982600 -1.47994000

H -1.28197500 -2.99960500 1.32384800

H 1.12533400 -2.53059200 1.61791400

H 1.12448400 -0.25090600 -2.02267700

H -1.25923000 -0.76423200 -2.35523000

C 2.65621800 -0.86297500 0.07788700

O 3.10468200 0.19285400 -0.35694900

O 3.38456100 -1.67886300 0.84277200

H 4.26285300 -1.28643700 0.97112000

N -2.83791100 -1.99571800 -0.61806300

H -3.19010100 -2.05054800 -1.56712800

H -3.24977700 -2.72325600 -0.04580900

H -3.04141600 -0.13540300 -0.05864300

C 1.83850300 3.46131900 -0.82773800

H 2.43679500 3.53301900 -1.73613100

H 0.99962100 4.15254200 -0.89003600

H 2.45080500 3.69610700 0.04551900

O 1.28636500 2.12677700 -0.72406900

H 2.00256400 1.44509700 -0.65461700

C -0.26704900 1.38396600 2.05371500

H 0.00947600 0.32987200 2.02190200

H 0.57067600 1.99386600 2.38634200

H -1.12091000 1.53952100 2.70990600

O -0.63551300 1.84293400 0.72415200

H 0.22158000 1.93279500 0.03681800

C -4.07060600 1.57944400 0.19571400

H -3.78743800 2.60348900 0.43651800

H -4.57379400 1.56701400 -0.77387700

H -4.74147400 1.20081500 0.97037700

O -2.85776200 0.80276400 0.14948100

H -1.49074500 1.38727100 0.39256400

Bridged (4-ABA)•(MeOH)4•H+

Electronic: −939.8676252hartree

ZPE corrected: −939.510975hartree

Enthalpy (298 K): −939.484262hartree

Gibbs (298 K): −939.572542hartree

XYZ Atomic Coordinates:

C -1.50677200 -2.10698000 -0.55939000

C -0.90462800 -2.81154700 0.49170200

C 0.45237600 -2.67455500 0.73693100

C 1.23171100 -1.80989700 -0.04458400

C 0.62553800 -1.10322400 -1.09295300

C -0.72604200 -1.25223100 -1.35217400

H -1.49984600 -3.47590200 1.10862100

H 0.91353700 -3.23592100 1.53901100

H 1.22237700 -0.45006000 -1.71660400

H -1.18389400 -0.71474100 -2.17560300

C 2.67132600 -1.62675800 0.20796500

O 3.35165200 -0.71198000 -0.24311400

O 3.20741600 -2.56324500 1.00007500

H 4.14808000 -2.36097100 1.12082100

N -2.89580700 -2.18743900 -0.77423400

H -3.44185600 -0.52268300 -0.01697100

H -3.17082500 -2.09201100 -1.74555600

H -3.33099300 -3.00866200 -0.37039900

C -4.71836200 0.63067800 1.01961000

H -4.75717800 1.69182000 1.26497600

H -5.60696200 0.37061700 0.43782800

H -4.70252600 0.05198000 1.94773600

O -3.52362400 0.41411300 0.25395100

H -2.32576700 1.45153300 0.12159800

C -1.69660400 2.64904300 -1.38021900

H -1.02028800 3.50024700 -1.45660100

H -1.39216500 1.87749900 -2.09261900

H -2.71236300 2.97843900 -1.60173700

O -1.63147500 2.15664600 -0.02936700

H -0.42813700 1.98760000 0.51332800

C 0.78047800 2.86377900 2.04561300

H 0.78749900 3.87947800 1.64632800

H -0.02225600 2.74967600 2.77114400

H 1.73543300 2.62985300 2.51334100

O 0.55407900 1.89883700 0.98481000

H 1.33714300 1.86150700 0.28965900

C 3.36516000 2.73733500 -0.94619200

H 3.87560200 2.52740400 -1.88764000

H 2.84234600 3.68984800 -1.03013500

H 4.09504700 2.78947400 -0.13418500

O 2.37508800 1.72179900 -0.68870200

H 2.79846200 0.83284200 -0.60579100

Bridged (4-ABA)•(MeOH)5•H+

Electronic: −1055.6602821hartree

ZPE corrected: −1055.249635hartree

Enthalpy (298 K): −1055.218744hartree

Gibbs (298 K): −1055.316245hartree

XYZ Atomic Coordinates:

C -1.60241400 -2.20346300 -0.68419000

C -0.74344300 -2.86828700 0.20131900

C 0.56456400 -2.43549400 0.36352600

C 1.03410500 -1.31416700 -0.33353900

C 0.17036800 -0.65050100 -1.21505600

C -1.13298300 -1.08711800 -1.39081300

H -1.09781600 -3.73270700 0.75253300

H 1.22981600 -2.96221800 1.03531300

H 0.52607300 0.20466500 -1.77558000

H -1.79206600 -0.55927000 -2.07061100

C 2.41466400 -0.81185600 -0.14331800

O 2.76779400 0.32457200 -0.47175500

O 3.23576400 -1.67352400 0.41679900

H 4.14408400 -1.27070600 0.54757500

N -2.95051400 -2.59994500 -0.81425500

H -3.82355000 -1.25324300 0.21256800

H -3.32529800 -2.46270100 -1.74650200

H -3.12870100 -3.55045800 -0.51091800

C -5.38563500 -0.50187900 1.21467000

H -5.60862300 0.46000800 1.67641800

H -6.14627700 -0.71705600 0.45777100

H -5.40976800 -1.27473300 1.98785300

O -4.07773300 -0.40491500 0.63181800

H -3.43770500 0.90324900 -0.11336100

C -3.80719200 2.76144800 -0.81364300

H -3.21052200 3.53427100 -1.29674300

H -4.58943100 2.43487200 -1.50165300

H -4.25909400 3.16674500 0.09605400

O -2.92916800 1.65955500 -0.51304600

H -1.76151400 1.90506800 0.22860800

C 6.13168500 0.33864200 -0.15461600

H 6.67009900 -0.14121400 -0.97645200

H 5.25680800 0.85388100 -0.54667800

H 6.78440400 1.05274900 0.35343500

O 5.62894800 -0.63870000 0.77949200

H 6.35194700 -1.16783700 1.13181100

C 1.90587300 3.61036800 -0.20600600

H 2.51230400 3.52890400 0.69957900

H 2.54648300 3.81366900 -1.06559100

H 1.18830200 4.42228300 -0.09332400

O 1.15805600 2.39913400 -0.43553000

H 1.77078800 1.61854500 -0.50736500

C -0.79602800 1.02065300 1.85872200

H 0.10100400 1.22791100 2.43927700

H -1.67555900 1.09563900 2.49496400

H -0.73785100 0.03333200 1.40037300

O -0.90236400 2.04692400 0.83396200

H 0.00349700 2.18153200 0.27418000

Bridged (4-ABA)•(MeOH)6•H+ (Isomer 1)

Electronic: −1171.4450834hartree

ZPE corrected: −1170.979327hartree

Enthalpy (298 K): −1170.942547hartree

Gibbs (298 K): −1171.056283hartree

XYZ Atomic Coordinates:

C 1.53038700 -0.92387400 0.08610300

C 0.91750400 -1.03695400 1.32726200

C -0.47296000 -1.07941100 1.38726200

C -1.22767400 -0.97102300 0.21688400

C -0.58837700 -0.88391200 -1.02366800

C 0.79655900 -0.87191700 -1.09399000

H 1.51626800 -1.06849700 2.22961100

H -0.97630000 -1.16521500 2.34148200

H -1.18001000 -0.80056800 -1.92552700

H 1.30273000 -0.78463900 -2.04809900

C -2.71626400 -0.85785900 0.26230100

O -3.34899900 -0.29054400 -0.61933300

O -3.26220600 -1.39213600 1.33687100

H -4.25373100 -1.24919400 1.33823500

N 2.98210600 -0.74585200 -0.00013700

H 3.38901100 -1.36539900 -0.72816500

H 3.13804200 0.27451100 -0.25477600

H 3.44467200 -0.89699900 0.91439300

C -2.66143800 2.98593900 -2.14942500

H -1.96339300 3.77881200 -2.41941900

H -3.23148600 2.70179400 -3.03905500

H -3.34818600 3.36318800 -1.38423200

O -1.88642400 1.88452500 -1.66179000

H -2.47841700 1.15680200 -1.39708700

C 2.99216400 -3.69321500 -2.26034800

H 2.73411200 -3.83621400 -3.31250200

H 3.56988800 -4.54734500 -1.89796200

H 2.07455300 -3.60710200 -1.67925900

O 3.71490100 -2.45833500 -2.07279500

H 4.52388000 -2.47170900 -2.59465900

C 3.55024000 2.88826500 -1.09646600

H 3.38609200 3.87838700 -0.66241300

H 4.61792200 2.66617700 -1.06987100

H 3.21185000 2.89213200 -2.13733500

O 2.87365200 1.88245300 -0.33273100

H 1.90077400 2.07905200 -0.29963700

C -0.24719700 2.76208500 1.14343000

H -0.84471400 1.95971000 1.58958800

H 0.59257600 2.98217800 1.80463900

H -0.86395700 3.66162200 1.05062100

O 0.28827900 2.36617100 -0.11904700

H -0.45353500 2.16120100 -0.73250200

C 4.16686500 0.87033500 2.88759900

H 3.68723000 1.10605400 3.84098600

H 5.22140500 1.15587400 2.92189200

H 3.67426500 1.42241300 2.08634200

O 4.01887000 -0.53196600 2.57258600

H 4.50191200 -1.06634200 3.21099900

C -6.58990100 -0.75075000 0.14273200

H -7.38897000 -0.02476700 0.31192800

H -5.86164000 -0.34156000 -0.55465000

H -7.00511200 -1.67613700 -0.26586000

O -5.86881000 -1.00174600 1.36696700

H -6.44602400 -1.41087600 2.01938200

Bridged (4-ABA)•(MeOH)6•H+ (Isomer 2)

Electronic: −1171.4432992hartree

ZPE corrected: −1170.97617hartree

Enthalpy (298 K): −1170.939986hartree

Gibbs (298 K): −1171.051988hartree

XYZ Atomic Coordinates:

C -0.52406600 -0.05417600 0.11916700

C -0.52860400 -0.89175100 -0.99026300

C 0.53767900 -1.76992100 -1.17038100

C 1.59765800 -1.77904700 -0.25819400

C 1.55949300 -0.95761900 0.87321600

C 0.49154600 -0.09671000 1.06859000

H -1.33774000 -0.83856800 -1.70880300

H 0.56555900 -2.41992100 -2.03507900

H 2.38111000 -0.96855600 1.57625100

H 0.47591700 0.57875600 1.91515600

C 2.83123300 -2.57622500 -0.49776000

O 3.90968600 -2.31112900 -0.00431000

O 2.64772300 -3.60542000 -1.33688400

H 3.50003500 -4.05018000 -1.46749500

N -1.57550900 0.95312000 0.28683600

H -2.14771700 0.73271400 1.11733900

H -1.09109600 1.88841500 0.41398400

H -2.22383100 0.97656700 -0.54224600

C 5.69940800 0.91894300 0.80889200

H 5.65513700 1.98504600 1.03146100

H 6.20854300 0.40665700 1.63035400

H 6.26388900 0.77262000 -0.11738200

O 4.34679300 0.45903700 0.67544000

H 4.34049700 -0.48943200 0.46568400

C -2.56781600 -1.51709200 2.77881400

H -1.72821800 -1.32787300 3.45096500

H -3.29692500 -2.17004600 3.26326500

H -2.20329900 -1.99221400 1.86955500

O -3.18884500 -0.27182800 2.36720900

H -3.54970500 0.17589500 3.14137900

C 0.05071700 4.42583200 0.68446000

H 0.23692700 4.86934400 -0.29852100

H -0.94753800 4.71190100 1.01867100

H 0.78437200 4.81066500 1.39798000

O 0.10072800 2.99510400 0.62685100

H 0.99865000 2.69590400 0.33250500

C 2.40360100 1.80199800 -1.71517900

H 2.08968500 0.76366200 -1.87194200

H 1.68397800 2.46399600 -2.19938600

H 3.38350200 1.95504400 -2.17693700

O 2.43092900 2.13315900 -0.32576200

H 3.09590000 1.56019300 0.11399800

C -3.99501300 1.50155500 -2.68313300

H -4.49017300 0.91682400 -3.46311200

H -4.72775500 2.15172400 -2.19501300

H -3.22363100 2.11796500 -3.14497400

O -3.34764600 0.63931100 -1.73665900

H -4.00361900 0.08471300 -1.26244000

C -5.88885000 -1.69756400 0.04721700

H -6.72992300 -1.21521000 0.55437100

H -6.16584700 -1.88944600 -0.98890900

H -5.66623500 -2.65288700 0.53239300

O -4.73434900 -0.84626300 0.02441400

H -4.42394100 -0.66122200 0.92400600

Bridged (4-ABA)•(MeOH)7•H+ (Isomer 1)

Electronic: −1287.2412159hartree

ZPE corrected: −1286.720682hartree

Enthalpy (298 K): −1286.680203hartree

Gibbs (298 K): −1286.804003hartree

XYZ Atomic Coordinates:

C 0.87275500 1.31889000 -0.05722400

C 0.45661300 2.52744300 -0.60897000

C -0.85792600 2.94012900 -0.42010100

C -1.74848200 2.13415800 0.29920200

C -1.30778500 0.92697100 0.85183000

C 0.00715600 0.51658600 0.67987600

H 1.15184700 3.13323700 -1.17764300

H -1.19813300 3.87700500 -0.84075200

H -1.99484700 0.30615200 1.41069600

H 0.34930600 -0.41912100 1.10558000

C -3.17635000 2.51232700 0.46711400

O -4.05126700 1.75193800 0.83615500

O -3.42628100 3.79361300 0.15867400

H -4.37535900 3.95570500 0.27569000

N 2.23819500 0.85141500 -0.28297900

H 2.85588100 1.61883200 -0.60173300

H 2.64140500 0.40009100 0.58037900

H 2.23540300 0.06915200 -1.00300000

C 3.78372400 -0.59981700 2.97516800

H 4.33673500 -1.50887700 3.22864500

H 4.48904000 0.22954000 2.91399000

H 3.05330100 -0.38642800 3.76272800

O 3.15174300 -0.72787200 1.69694500

H 2.51824800 -1.48036500 1.70153200

C 0.59979300 -3.39956200 2.51087400

H -0.49098100 -3.30586700 2.50657500

H 0.87439800 -4.44940300 2.36809000

H 0.97504400 -3.06880900 3.47974500

O 1.19297800 -2.56532500 1.50957400

H 0.83328500 -2.79199800 0.62544900

C 3.34191600 -2.06047800 -2.06163700

H 3.21927400 -2.82533300 -2.83325500

H 4.14209400 -1.38602100 -2.36802200

H 3.61809100 -2.53330300 -1.11349800

O 2.14393700 -1.28027000 -1.92618800

H 1.40729100 -1.87668700 -1.66218800

C -5.17517500 -1.75915900 0.61769700

H -5.90208800 -1.40377500 -0.11938400

H -4.94676700 -2.80518100 0.41293000

H -5.60526700 -1.68043800 1.62022300

O -3.94301500 -1.03026200 0.53144600

H -4.10347700 -0.08367500 0.69257100

C 4.00100800 4.15721000 -0.09398800

H 5.00476300 4.04117600 0.32302200

H 3.89379400 5.15121400 -0.53511600

H 3.26656000 4.04405300 0.70343800

O 3.71614100 3.12928300 -1.06457400

H 4.32336900 3.20681200 -1.80787200

C -2.12462800 -0.62733100 -2.33998600

H -1.36029200 -0.87895500 -3.07688400

H -3.10493500 -0.66570800 -2.82423200

H -1.93956300 0.38915100 -1.97598300

O -2.03673300 -1.58187300 -1.28104900

H -2.74064200 -1.40945500 -0.61271300

C 0.02639600 -4.22612900 -1.58921000

H 0.97647600 -4.75049500 -1.48240600

H -0.22155600 -4.14321400 -2.65077800

H -0.75552000 -4.79449200 -1.07904300

O 0.17753100 -2.92325400 -0.99694500

H -0.68791000 -2.42967900 -1.06211400

Bridged (4-ABA)•(MeOH)7•H+ (Isomer 2)

Electronic: −1287.239921hartree

ZPE corrected: −1286.719437hartree

Enthalpy (298 K): −1286.678884hartree

Gibbs (298 K): −1286.801729hartree

XYZ Atomic Coordinates:

C -1.06038000 -1.33396300 0.13023600

C -0.25460800 -2.04204900 -0.75795900

C 1.12343300 -1.86931900 -0.70355600

C 1.68026000 -0.97282900 0.21716400

C 0.85524300 -0.29394700 1.11569800

C -0.52175000 -0.47695200 1.08043100

H -0.70026600 -2.71203200 -1.48393600

H 1.76960300 -2.40641700 -1.38532400

H 1.28706800 0.39075200 1.83272200

H -1.16934200 0.05464300 1.76554900

C 3.14489400 -0.68438200 0.22785500

O 3.60866300 0.34063100 0.71930900

O 3.87966600 -1.61409000 -0.34915900

H 4.84614100 -1.34652000 -0.29900900

N -2.51687400 -1.46877500 0.02676000

H -2.79295000 -2.47047600 0.00984500

H -2.99640000 -0.96292700 0.80463600

H -2.85207400 -0.97790000 -0.84250600

C -4.56433600 0.67944000 2.69643100

H -5.52008600 0.93354300 2.22699500

H -4.69210400 -0.22802200 3.28669800

H -4.25987700 1.49086600 3.36404600

O -3.55435800 0.41666100 1.71481800

H -3.37852300 1.21448000 1.17142100

C 7.48566700 -0.49772700 -0.70631200

H 7.35801900 0.22006500 -1.52216600

H 8.30449900 -0.17959900 -0.05616300

H 7.72485100 -1.47522100 -1.12253300

O 6.27235700 -0.65534800 0.04748800

H 6.00156700 0.17666200 0.45566400

C -3.99925500 0.45100900 -3.06867400

H -3.61683000 1.25510200 -3.70458600

H -3.95471900 -0.48399400 -3.62726400

H -5.04163700 0.65913700 -2.80715400

O -3.18671200 0.29413500 -1.89979400

H -3.16814400 1.12046700 -1.37045700

C 2.75583000 3.88144500 0.98978000

H 3.43236400 4.02657200 0.14089000

H 2.02805200 4.69312000 1.00145400

H 3.32967300 3.91063100 1.92099000

O 2.02549600 2.65520300 0.87482600

H 2.64274800 1.90028600 0.85478300

C -1.94669800 -5.02456500 0.79050600

H -2.42468500 -5.34783800 1.71879300

H -1.58984400 -5.89313900 0.23175300

H -1.09848700 -4.38299300 1.02698900

O -2.84857800 -4.23361800 -0.01174100

H -3.60372100 -4.76871400 -0.27690700

C 0.12307200 1.85405200 -1.79106800

H -0.78185600 1.70298800 -2.38087200

H 0.80611500 2.50546700 -2.34474400

H 0.59762000 0.88058200 -1.63324100

O -0.26194700 2.44846400 -0.54939900

H 0.53578400 2.55389000 0.01791000

C -3.41953000 3.65175200 -0.19511600

H -4.50376400 3.53503000 -0.20145500

H -3.10736000 4.15400700 -1.11470500

H -3.13024000 4.26216100 0.66458000

O -2.83808400 2.33901300 -0.10811300

H -1.84617200 2.41657300 -0.16836900

Bridged (4-ABA)•(MeOH)8•H+ (Isomer 1)

Electronic: −1403.0310092hartree

ZPE corrected: −1402.457547hartree

Enthalpy (298 K): −1402.412358hartree

Gibbs (298 K): −1402.548819hartree

XYZ Atomic Coordinates:

C 0.89454700 1.45724500 -0.09758700

C 0.05540500 2.37240200 -0.72672600

C -1.32202300 2.22574400 -0.59889400

C -1.85046900 1.15856500 0.13590900

C -0.98873600 0.25461500 0.76456300

C 0.38814100 0.40234300 0.65507400

H 0.47509700 3.18475100 -1.30809300

H -1.99138200 2.92800000 -1.07773500

H -1.39520300 -0.56900100 1.33604900

H 1.05527400 -0.29989400 1.14084300

C -3.32494000 0.94592300 0.23924900

O -3.81878500 -0.10935700 0.61828500

O -4.03983200 1.99355400 -0.12424200

H -5.01815800 1.79075900 -0.06828800

N 2.34304700 1.57572000 -0.25563500

H 2.85148000 1.34421900 0.63680900

H 2.69352500 0.84669800 -0.94384900

H 2.61375700 2.52039800 -0.58054400

C 4.19485700 0.91993900 3.10291200

H 5.05035000 0.31244300 3.41264300

H 4.51355500 1.96095700 3.04057700

H 3.40021300 0.83742000 3.85211600

O 3.73412400 0.52799500 1.80587600

H 3.44752300 -0.41317100 1.81576200

C 2.47498000 -2.94807400 2.62005300

H 1.44211700 -3.31093300 2.60874400

H 3.15732900 -3.79209900 2.47754700

H 2.67625200 -2.49677800 3.59209000

O 2.67825900 -1.94010900 1.62409700

H 2.46309500 -2.29675000 0.73539800

C -3.51113400 -3.66364800 0.24261500

H -4.25934900 -3.52814900 -0.54541800

H -2.92981300 -4.56015800 0.02558200

H -4.01700000 -3.79586600 1.20382700

O -2.59739700 -2.56224500 0.29295200

H -3.08802700 -1.73216900 0.45086200

C 4.64993100 -0.68951600 -1.76398400

H 4.98266700 -0.96157300 -0.75687900

H 4.92437700 -1.47891700 -2.46905700

H 5.14943200 0.23170100 -2.06563400

O 3.23499300 -0.44800900 -1.79876300

H 2.76886600 -1.27789700 -1.54926100

C -7.13245100 0.44458400 0.86077800

H -7.97017100 -0.07545300 0.38946000

H -6.30763500 -0.24868900 1.01348800

H -7.44289600 0.85821600 1.82429600

O -6.62533800 1.47720300 -0.00863100

H -7.29365100 2.15472800 -0.15185600

C 2.54329100 5.32865600 -0.18780000

H 3.45104000 5.66068300 0.32295900

H 2.08791600 6.16757000 -0.71993800

H 1.83436300 4.95265300 0.54982000

O 2.81932000 4.23639200 -1.08740300

H 3.41536800 4.53121200 -1.78374400

C -0.88977400 -1.49463000 -2.45988200

H -1.09750400 -0.48585300 -2.08761800

H -1.76604500 -1.86895000 -2.99757600

H -0.04859000 -1.44654500 -3.15321800

O -0.52586600 -2.37741400 -1.39686300

H -1.27702100 -2.46468900 -0.76261400

C 2.41156500 -3.96678800 -1.45252000

H 3.47979000 -4.07961800 -1.26405500

H 1.87455200 -4.79013000 -0.97448900

H 2.23159500 -3.99688200 -2.53054200

O 2.00122100 -2.70270000 -0.90178500

H 1.01683900 -2.58892500 -1.03976500

Bridged (4-ABA)•(MeOH)8•H+ (Isomer 2)

Electronic: −1403.0301356hartree

ZPE corrected: −1402.456287hartree

Enthalpy (298 K): −1402.411278hartree

Gibbs (298 K): −1402.546305hartree

XYZ Atomic Coordinates:

C -0.97257100 1.40102200 -0.35013700

C -0.19737600 2.42886000 0.17891400

C 1.18939800 2.32637500 0.12576700

C 1.78881300 1.19361300 -0.43632800

C 0.99053100 0.18107600 -0.97602900

C -0.39343700 0.28127400 -0.93638800

H -0.67283600 3.29630600 0.62181100

H 1.81026900 3.11586600 0.52807600

H 1.45035300 -0.68850300 -1.42457800

H -1.01222400 -0.50574400 -1.34744000

C 3.27166500 1.02976600 -0.44933400

O 3.81864700 -0.05317100 -0.64407300

O 3.93628600 2.14529700 -0.22194000

H 4.92064900 1.95509900 -0.25804500

N -2.43042200 1.46909500 -0.25323200

H -2.89500300 1.02292000 -1.09162700

H -2.74645100 0.90487800 0.58156900

H -2.75673800 2.44694600 -0.15325100

C 3.49390900 -3.60932700 -0.05488800

H 4.23418200 -3.45225000 0.73665100

H 2.89780300 -4.48813800 0.19185200

H 4.00866900 -3.78759000 -1.00374000

O 2.59558400 -2.49872600 -0.16090900

H 3.09528700 -1.68306600 -0.35954900

C -3.18823500 -0.06136700 3.15427800

H -3.55686700 0.94662500 3.34872500

H -3.88715400 -0.77714300 3.59688000

H -2.20614700 -0.17337200 3.62609700

O -3.11084800 -0.23114900 1.73610400

H -2.76969200 -1.12972300 1.52327900

C -4.15097500 4.61094200 1.07104400

H -5.11575300 4.76889600 0.58191400

H -4.25215400 3.81485100 1.80852200

H -3.83608400 5.52616700 1.57836900

O -3.15150000 4.17502400 0.12800100

H -3.02843100 4.84968100 -0.54827500

C -4.78493100 0.11333000 -2.93224700

H -5.06071800 1.16199600 -3.04980000

H -4.75149700 -0.35057100 -3.92210200

H -5.54248600 -0.38875100 -2.32192300

O -3.49719700 0.07132300 -2.30747800

H -3.21020000 -0.85879000 -2.16713000

C -1.62982100 -3.19795200 -2.39983500

H -1.96898600 -4.23470000 -2.31228500

H -1.69197100 -2.89677800 -3.44575900

H -0.58546800 -3.13089600 -2.07404600

O -2.46756600 -2.31485800 -1.64642600

H -2.36817900 -2.49825800 -0.68897100

C 7.65952500 1.50574100 0.17517600

H 8.47334400 1.08593800 -0.42145300

H 7.80703300 2.58088200 0.26621100

H 7.65957100 1.05638100 1.17280600

O 6.39738000 1.31670300 -0.48485900

H 6.20026800 0.37961100 -0.60660300

C -2.43644300 -3.83779300 1.68937700

H -1.92939000 -4.70180100 1.25179500

H -3.51119700 -3.93963000 1.53843400

H -2.22395800 -3.80121000 2.76137900

O -2.01916500 -2.62130900 1.04317100

H -1.03942800 -2.49131400 1.18260700

C 0.84480100 -1.13400000 2.40577200

H 0.82861400 -0.16577500 1.89387600

H 0.10004000 -1.12640800 3.20343400

H 1.83032200 -1.28855900 2.85477200

O 0.51686500 -2.20065400 1.51476900

H 1.25855500 -2.33491900 0.87840700

Figure S6. Relative Gibbs’ Energies

Figure S6.Standard Gibbs’ energies of the (centre) bridged and (right) O-protonated isomers of (4-ABA•H+)(CH3OH)n (n = 1 – 8) relative to the associated N-protonated structures [B3LYP-GD3/6-311++G(d,p)].

1