Formation and Isomerization of Dicyclopenta[de,mn]anthracene. Electronic Structure Study
Sonja Stanković,*Svetlana Marković, Slavko Radenković, and Ivan Gutman
Faculty of Science, University of Kragujevac, P.O. Box 60, 34000 Kragujevac, Serbia
Electronic Supplementary Material:Total energies, enthalpies, free energies (Table 1)and Cartesian coordinates for all computed species (I1, TS1, I2, TS2, I3, TS3, I4, TS4, P1, TS5, I5, TS6, I6, TS7, I7, TS8, and P3),IRC calculation for TS1 (Fig. 1).
1
Table 1. The values in kJ/mol of free energy (ΔG298), total energy (ΔE), and enthalpy (ΔH298) for all investigated species.
I1 / TS1 / I2 / TS2 / I3 / TS3 / I4 / TS4 / P1 / TS5 / I5 / TS6 / I6 / TS7 / I7 / TS8 / P3ΔG298 / 153.98 / 464.69 / 308.92 / 345.55 / 45.26 / 385.02 / 245.03 / 294.28 / 0.00 / 354.89 / 332.20 / 349.64 / 42.12 / 354.20 / 212.45 / 266.98 / -95.79
ΔE / 161.48 / 468.95 / 313.65 / 349.13 / 48.49 / 387.46 / 246.66 / 294.60 / 0.00 / 355.09 / 332.23 / 348.52 / 42.96 / 356.09 / 215.96 / 267.15 / -96.94
ΔH298 / 167.46 / 472.74 / 317.61 / 351.95 / 51.28 / 389.66 / 247.84 / 294.59 / 0.00 / 355.49 / 333.00 / 348.01 / 43.00 / 357.63 / 219.19 / 268.03 / -97.55
The energies are calculated relative to P1.
1
Fig. 1. The results of the IRC calculation for the TS1
Cartesian coordinates for all investigated species
I1E= -691.773761 HartreeH= -691.759012 HartreeG= -691.813974 Hartree
0 1
H -4.08480500 -1.23627600 0.00002800
C -3.14133800 -0.70468000 0.00001600
C -1.96271200 -1.42280100 0.00002400
C -1.96270600 1.42281000 -0.00002100
C -0.69908000 -0.72124700 0.00001400
C -3.14133500 0.70469400 -0.00001200
C -0.69907700 0.72125100 -0.00001200
C 0.52171000 -1.39944800 0.00002600
H -4.08479900 1.23629300 -0.00002200
H 0.51870600 2.48321100 -0.00004400
C 1.74397500 -0.71978600 0.00001400
H 0.51869400 -2.48321400 0.00004500
C 2.99663400 -1.40567000 0.00002600
C 1.74397800 0.71977900 -0.00001300
H 2.99396100 2.49051100 -0.00004200
C 0.52171600 1.39944500 -0.00002500
C 4.17440100 -0.71212500 0.00001200
H 2.99395000 -2.49052500 0.00004400
H 5.11971400 -1.24310200 0.00002000
C 4.17440400 0.71210500 -0.00001300
H 5.11972000 1.24307800 -0.00002400
C 2.99664100 1.40565600 -0.00002500
C -2.00106300 -2.84667100 0.00004400
C -2.04283400 -4.05100400 -0.00006700
H -2.08600100 -5.11254600 -0.00008000
C -2.00105100 2.84668000 -0.00003900
C -2.04279400 4.05101400 0.00004800
H -2.08595500 5.11255600 0.00008700
TS1E=-691.656628 HartreeH=-691.642718 HartreeG=-691.695607Hartree
0 1
H -0.01094400 0.04513000 -0.04389400
C -0.01241000 0.05500200 1.04035300
C 1.18383600 0.08271300 1.74283700
C -1.31675400 0.09926100 3.13306700
C 1.09729700 0.05843100 3.16002500
C -1.24008100 0.05000000 1.74093100
C -0.09603000 0.10823000 3.90250200
C 2.37292700 0.01636800 3.74553600
H -2.16663000 0.03866000 1.17975900
H -0.86593600 0.36985000 5.90209700
C 2.51225200 0.16729100 5.15171100
H 2.98328500 -0.92291900 3.21534100
C 3.75262700 0.16353400 5.83637800
C 1.28761800 0.31341700 5.91528000
H 0.48452400 0.61724400 7.90190700
C 0.02390100 0.25898200 5.29248500
C 3.80367600 0.32567100 7.19844500
H 4.66816500 0.04850700 5.26724900
H 4.76160100 0.33250900 7.70582900
C 2.61387200 0.49402300 7.95195200
H 2.67569200 0.62797700 9.02559400
C 1.39566300 0.48814100 7.32778300
C -2.58136700 0.16142700 3.78077300
C -3.65021800 0.21027300 4.33549200
H -4.59786700 0.25252700 4.81423500
C 2.57282400 0.19140600 1.30202200
C 3.36405100 0.09100000 2.40766300
H 4.43108600 0.15870600 2.55713400
I2E= -691.715793 HartreeH= -691.701814 HartreeG= -691.754950 Hartree
0 1
H -3.63322800 2.43469700 -0.00011500
C -2.90048000 1.63568400 -0.00003700
C -1.54395000 1.93179300 -0.00004900
C -2.40563800 -0.77847800 0.00008200
C -0.61729500 0.84276800 0.00002400
C -3.31256300 0.28676800 0.00005000
C -0.98655200 -0.52383600 0.00005500
C 0.68920700 1.30383400 0.00001100
H -4.37001700 0.05209600 0.00006000
H -0.17038600 -2.52352400 0.00006000
C 1.73796500 0.37491300 -0.00001200
H 1.07866300 3.29681300 -0.86772300
C 3.11709000 0.74123400 -0.00001600
C 1.39200800 -1.03952000 0.00000100
H 2.20618900 -3.04703200 -0.00000600
C 0.05069900 -1.46217100 0.00004500
C 4.09875100 -0.21068500 -0.00002500
H 3.37501200 1.79418400 -0.00001100
H 5.14188400 0.08474700 -0.00003000
C 3.76528100 -1.59422800 -0.00002700
H 4.55840800 -2.33314700 -0.00003100
C 2.45777700 -1.99178900 -0.00001300
C -2.89329100 -2.11475700 0.00011700
C -3.30032000 -3.24875400 -0.00013900
H -3.66748500 -4.24608300 -0.00024000
C -0.87692000 3.21887600 -0.00022800
C 0.59535500 2.82678300 0.00011800
H 1.07820400 3.29664000 0.86830300
TS2E= -691.702276 HartreeH= -691.688730 HartreeG= -691.740996 Hartree
0 1
H -0.01104300 -0.01901400 -0.03239600
C -0.01828400 -0.00963400 1.05192600
C 1.15960100 -0.00027400 1.76449400
C -1.33840000 0.02607100 3.14007100
C 1.07733200 0.02394900 3.18371300
C -1.25574400 0.00513100 1.75093900
C -0.12398100 0.03113500 3.92268800
C 2.34884000 0.01784100 3.74540500
H -2.17956600 0.00330900 1.18518800
H -0.88818000 0.04524400 5.94041000
C 2.48871500 0.01935200 5.14320600
H 3.23975300 -1.02961800 1.88122600
C 3.73952500 0.00501000 5.82393300
C 1.26625900 0.03734500 5.93120000
H 0.47313600 0.06080900 7.94581500
C -0.00145600 0.04041600 5.31589200
C 3.79605200 0.01186900 7.19161700
H 4.65289800 -0.01157800 5.24044300
H 4.75689400 0.00104100 7.69380600
C 2.60499200 0.03366000 7.96703100
H 2.67291000 0.04013000 9.04875200
C 1.38248700 0.04551400 7.35453100
C -2.60895900 0.04456600 3.78216300
C -3.67916400 0.06011300 4.33534700
H -4.62827100 0.07434100 4.81289700
C 2.57648700 0.06354100 1.31222400
C 3.27721300 -0.00023500 2.57466000
H 4.34873100 0.15918800 2.64914000
I3E= -691.816806 HartreeH= -691.803274 HartreeG= -691.855392 Hartree
0 1
H 3.64900400 2.39217200 -0.00009300
C 2.88937500 1.61746000 -0.00009900
C 1.54716500 1.91488000 -0.00000300
C 2.40276900 -0.80764500 -0.00004100
C 0.62460200 0.82944800 -0.00001900
C 3.29894800 0.25425700 -0.00012100
C 0.98347500 -0.52614100 -0.00007100
C -0.68615700 1.31445900 0.00002100
H 4.35887400 0.02978600 -0.00020200
H 0.14282300 -2.51611900 -0.00011900
C -1.74884500 0.39431100 0.00001200
C -3.12484600 0.76313100 0.00005000
C -1.40813400 -1.02072300 -0.00003900
H -2.22477100 -3.02583100 -0.00008700
C -0.06860900 -1.45251300 -0.00008000
C -4.10990500 -0.18687100 0.00003900
H -3.38260500 1.81608100 0.00008800
H -5.15223000 0.11248300 0.00006800
C -3.78315600 -1.57093600 -0.00001100
H -4.57926400 -2.30676300 -0.00001900
C -2.47600000 -1.97032800 -0.00004800
C 2.87574200 -2.14993500 -0.00003600
C 3.26822900 -3.28957400 0.00024500
H 3.62179100 -4.29142600 0.00037800
C -0.57982600 2.78103200 -0.00009100
H -1.41407500 3.46905600 -0.00015100
C 0.73737400 3.13518900 0.00024600
H 1.12724200 4.14355700 0.00041300
TS3E= -691.687672 HartreeH= -691.674366 HartreeG= -691.725958 Hartree
0 1
H 0.03654600 0.02058100 -0.00524600
C 0.00887300 -0.00420600 1.07879400
C 1.17416900 -0.00571800 1.83106200
C -1.35939100 -0.16181600 3.12991600
C 1.05852000 -0.04698400 3.25521100
C -1.24219500 -0.08114000 1.73467900
C -0.15270500 -0.15288300 3.93981100
C 2.31276200 -0.13078400 3.85358400
H -2.15129600 -0.11384200 1.14590100
H -1.97689100 0.72243100 5.64271400
C 2.38089200 -0.26929100 5.25355100
C 3.59537900 -0.36232600 5.98907500
C 1.11065900 -0.26228100 6.00200200
H 0.24211000 -0.28049100 7.97555400
C -0.10965400 -0.18611300 5.31917900
C 3.59235700 -0.42459700 7.35725700
H 4.53451900 -0.37888500 5.44691200
H 4.53118800 -0.49432800 7.89564900
C 2.37314600 -0.38939900 8.08680700
H 2.39836400 -0.43232000 9.16962900
C 1.17751100 -0.30243000 7.42871700
C -2.54968600 -0.21262400 3.88372400
C -2.55392700 -0.12048000 5.20838900
H -3.12023100 -0.71777900 5.91087300
C 3.27755700 -0.11208100 2.74132900
H 4.35312400 -0.16545900 2.84444200
C 2.60662700 -0.04286000 1.55000000
H 3.05564700 -0.01341500 0.56754100
I4E= -691.741310 HartreeH= -691.728392 HartreeG= -691.779288 Hartree
0 1
H 4.32873300 -1.15748000 0.00011200
C 3.36362300 -0.66168900 0.00006000
C 2.17952900 -1.39815800 -0.00001700
C 2.12818500 1.47976200 -0.00001600
C 0.96758100 -0.66099900 -0.00008700
C 3.33797000 0.77074300 0.00005600
C 0.94551800 0.70291000 -0.00007400
C -0.16723000 -1.45125600 -0.00005200
H 4.27819000 1.31180200 0.00012300
H -0.08728400 3.47745200 0.86929200
C -1.41299000 -0.77479400 -0.00003600
C -2.66276500 -1.45517800 -0.00000300
C -1.43691700 0.70939700 -0.00002200
H -2.73047300 2.44114000 0.00001800
C -0.22814200 1.43705900 -0.00002700
C -3.85133600 -0.77440000 0.00003000
H -2.66018400 -2.53947200 -0.00001100
H -4.78690400 -1.32252800 0.00005000
C -3.87713700 0.64575800 0.00003500
H -4.83006400 1.16223900 0.00006000
C -2.70904800 1.35696700 0.00001100
C 1.79763300 2.89820700 -0.00003400
C 0.25558800 2.90047400 0.00001400
H -0.08752500 3.47767900 -0.86900100
C 0.36627100 -2.83191400 0.00006400
H -0.22456500 -3.73833900 0.00012800
C 1.73946100 -2.80047800 -0.00002700
H 2.38531200 -3.66695900 -0.00002200
TS4E= -691.723047 HartreeH= -691.710582 HartreeG= -691.760527 Hartree
0 1
H -0.01504000 -0.03063400 -0.02783800
C -0.01862900 -0.00683600 1.05696600
C 1.16202600 0.01741300 1.77988000
C -1.39397600 0.01355200 3.10988900
C 1.03964000 0.04357400 3.18668200
C -1.30490900 -0.01057500 1.72867700
C -0.17266300 0.04738400 3.81452600
C 2.24919100 0.01870700 3.85954100
H -2.20206800 -0.03332800 1.11903400
H -2.31937600 0.11996000 6.31407600
C 2.19701000 -0.00214400 5.27553400
C 3.36734900 -0.03111500 6.08629500
C 0.88119600 -0.00786900 5.96012700
H -0.08346300 -0.05255600 7.89372600
C -0.30600800 0.02079000 5.18949000
C 3.29421100 -0.06543700 7.45295000
H 4.33386500 -0.02549000 5.59495800
H 4.20263600 -0.08633700 8.04419200
C 2.03498900 -0.07435000 8.10817800
H 1.99789800 -0.10249600 9.19124900
C 0.87359800 -0.04658000 7.38398900
C -2.52175300 0.04836800 4.10880300
C -1.81027700 -0.01799500 5.36494200
H -2.39184900 -1.04912000 4.95430200
C 3.26259400 -0.00811500 2.76941300
H 4.33541500 -0.02736700 2.90426000
C 2.62998500 -0.00669600 1.55862700
H 3.12223100 -0.02598700 0.59635700
P1E= -691.835277 HartreeH= -691.822808 HartreeG= -691.872633 Hartree
0 1
H -4.81309800 1.24325800 0.00001700
C -3.86899900 0.71024900 0.00001800
H -2.70061800 2.48977400 0.00000800
C -2.69036800 1.40550100 0.00001600
C -2.69036700 -1.40550100 -0.00000200
C -1.42880500 0.74242500 0.00001700
C -3.86899900 -0.71024900 0.00000800
C -1.42880500 -0.74242400 0.00001000
C -0.19995400 1.44312700 -0.00001300
H -4.81309800 -1.24325800 0.00000100
H -2.70061800 -2.48977400 -0.00002200
C 0.95827500 0.68045300 -0.00002700
C 2.14840800 1.44195200 -0.00001700
C 0.95827500 -0.68045300 -0.00003100
C -0.19995500 -1.44312700 -0.00002400
C 3.33051200 0.72819900 -0.00004900
H 4.29390500 1.22758300 -0.00000300
C 3.33051200 -0.72819900 -0.00004700
H 4.29390500 -1.22758400 0.00001600
C 2.14840800 -1.44195300 -0.00000900
C 1.66202200 -2.84862200 0.00017400
H 2.28654400 -3.73115600 0.00029700
C 0.29769100 -2.84826900 -0.00011200
H -0.31942600 -3.73635500 -0.00017200
C 0.29769200 2.84826900 -0.00005400
H -0.31942600 3.73635500 -0.00007800
C 1.66202200 2.84862200 0.00010200
H 2.28654500 3.73115600 0.00018000
TS5E= -691.700003 HartreeH= -691.687385 HartreeG= -691.737437 Hartree
0 1
H 0.00240900 -0.02555800 0.01019500
C 0.00325600 -0.01338700 1.09423200
H 2.12893600 0.00487700 1.23391300
C 1.19103700 0.00424300 1.77799200
C -1.25099000 -0.00113900 3.16372100
C 1.23306700 0.02332100 3.19954000
C -1.22957700 -0.01792500 1.79313200
C -0.05264300 0.02968600 3.92788600
C 2.44936800 -0.02001800 3.93086400
H -2.15952100 -0.03278800 1.23625500
H -2.19897300 -0.00026200 3.69007900
C 2.35472400 0.00409600 5.30870200
C 3.59398300 -0.26107400 5.97611200
C 1.17595100 0.07782600 5.97478500
C -0.05176300 0.03258400 5.34951200
C 3.55741200 -0.44824600 7.33552200
H 4.47503000 -0.65094500 7.88105200
C 2.29675100 -0.54956600 8.14014200
C 1.11848800 -0.16658000 7.39864800
C -0.37098600 -0.31337500 7.63920100
H -0.81857500 -0.48970000 8.60701400
C -1.02598100 -0.18556300 6.45883300
H -2.09871100 -0.26125400 6.34141400
C 3.90098800 -0.23617800 3.67488100
H 4.36246400 -0.30422400 2.69868300
C 4.56678300 -0.36849100 4.85777800
H 5.62568600 -0.55645200 4.96462500
H 1.57044800 0.67801100 8.16528300
I5E= -691.708715 HartreeH= -691.695950 HartreeG= -691.746080 Hartree
0 1
H 4.78375100 -1.27900500 -0.18874000
C 3.84781300 -0.73711400 -0.11203700
H 2.67358100 -2.50875900 0.08167300
C 2.66594300 -1.42495700 0.04090800
C 2.66714200 1.37100400 -0.07223400
C 1.42589400 -0.74978100 0.14769700
C 3.84866700 0.67195200 -0.17245900
C 1.42848100 0.71013100 0.10679800
C 0.16849300 -1.42914400 0.19873500
H 4.78506700 1.20486300 -0.29258900
H 2.67813100 2.45477900 -0.10900000
C -0.97154100 -0.66408300 0.33817800
C -2.18085200 -1.42438300 0.05367200
C -0.96185200 0.69503000 0.43688900
C 0.18745900 1.42353300 0.21059100
C -3.36666600 -0.70575500 -0.12375100
H -4.30849500 -1.22340900 -0.29431600
C -3.28555000 0.67480100 -0.42015600
C -2.21344100 1.49092900 0.25225800
C -1.62412400 2.81299400 -0.22735200
H -2.22144200 3.68519700 -0.45825200
C -0.27156800 2.77582800 -0.15878200
H 0.37692100 3.61340200 -0.38179300
C -0.33325200 -2.77943600 -0.10690800
H 0.28381900 -3.65416200 -0.26932100
C -1.70785800 -2.77074400 -0.20511700
H -2.32575200 -3.62005100 -0.45821900
H -2.66471200 1.68231500 1.24898000
TS6E= -691.702506 HartreeH= -691.690233 HartreeG= -691.739437 Hartree
0 1
H 0.00167900 -0.00865200 0.00982400
C 0.00288600 -0.00438800 1.09411100
H 2.13340500 0.00448800 1.23188000
C 1.19742100 0.00301300 1.77931000
C -1.22627400 0.00225000 3.17060800
C 1.24180800 0.01464400 3.19316200
C -1.22009400 -0.00371600 1.79413900
C -0.02339700 0.01081500 3.91714000
C 2.47259400 -0.03596100 3.93046400
H -2.15584400 -0.00528500 1.24700500
H -2.17099800 0.00586800 3.70304300
C 2.38846300 0.01986200 5.31232200
C 3.61422400 -0.36798900 5.95667700
C 1.19356100 0.06946700 5.99273900
C -0.02859500 -0.00190900 5.35407500
C 3.34572200 -0.79984900 7.25430100
H 4.07782600 -1.20991000 7.94401600
C -0.49363500 -0.03943500 7.62518200
H -1.02092900 -0.09720200 8.56704400
C -1.05708200 -0.06916100 6.39597100
H -2.11932600 -0.16198200 6.21071400
C 3.87431400 -0.35871300 3.66938500
H 4.32811000 -0.45276000 2.69183200
C 4.54079100 -0.57333800 4.86456900
H 5.57546900 -0.87390600 4.95249400
C 1.00387100 0.14732900 7.54262600
C 1.96557900 -0.93701000 7.54386800
H 1.33579900 1.12172600 7.92758400
I6E= -691.818912 HartreeH= -691.806427 HartreeG= -691.856587 Hartree
0 1
C -0.10754200 -1.32473300 0.12940900
C -0.80750300 0.96892400 0.26137300
C 1.51041600 0.66390000 0.05132600
C 1.25961900 -0.78002900 0.08863100
C 2.84237500 1.11294100 -0.05196700
C 3.90447200 0.23128000 -0.10230500
C 3.66968300 -1.14975000 -0.05239100
C 2.37704600 -1.63365500 0.03919600
C -3.02945200 0.91752700 -0.03388100
C -1.96710900 1.78475200 0.07502600
C -1.10228000 -0.37791400 0.23517000
C -1.37246400 3.13367800 -0.12225700
C -0.00797500 3.01597600 -0.11013900
H 3.02542200 2.18156700 -0.08337100
H 4.91870900 0.60690600 -0.17672900
H 4.50308000 -1.84229200 -0.08703000
H 2.21617700 -2.70530100 0.07444900
H 0.67627300 3.84283300 -0.24789700
H -1.90869800 4.06121200 -0.26521000
H -4.06553400 1.15861300 -0.23578300
C -2.95588500 -1.78972800 -0.12065200
C -2.50034700 -0.50120700 0.06549300
H -4.00051300 -2.02939300 -0.28869400
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1