Supporting information
Thermodynamic investigation of tautomerism in triazine oximes
Roxana-Diana Paşca1*, Atena Moldovan2, Ossi Horovitz1, Alexandru Lupan2
1 Department of Chemical Engineering, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University,Cluj-Napoca, Romania
2 Department of Chemistry, Faculty of Chemistry and Chemical Engineering,
Babeş-Bolyai University,Cluj-Napoca, Romania
Email:
Table S1. Energy ranking for all of the monoxime computed structures.
Table S2. The optimized monoxime structures up to 19 kcal/mol from the global minimum.
Table S3. Energy ranking for all of the dioxime computed structures.
Table S4. The optimized dioxime structures up to 9 kcal/mol from the global minimum.
Table S1. Energy ranking for all of the monoxime computed structures.
Nr / Compound / ZPcorr Energy (a.u.) / ΔEglobal(kcal/mol) / ΔEcmpd
(kcal/mol) / Rank / Enthalpy
(a.u.) / ΔHglobal
(kcal/mol) / Free Energy
(a.u.) / ΔGglobal
(kcal/mol)
1 / Cmpd_C_AAa / -579.439517 / 0.00 / 0.00 / 1 / -579.428965 / 0.00 / -579.474731 / 0.00
2 / Cmpd_C_BAa / -579.439516 / 0.00 / 0.00 / ##### / ####
3 / Cmpd_D_ABb2 / -579.436933 / 1.62 / 0.00 / 2 / -579.426926 / 1.28 / -579.471410 / 2.08
4 / Cmpd_D_BBb1 / -579.436496 / 1.90 / 0.27 / 3 / -579.426443 / 1.58 / -579.471059 / 2.30
5 / Cmpd_D_CBb1 / -579.436495 / 1.90 / 0.27 / ##### / ####
6 / Cmpd_D_AAa1 / -579.436040 / 2.18 / 0.56 / 4 / -579.425490 / 2.18 / -579.471255 / 2.18
7 / Cmpd_D_CAa1 / -579.435798 / 2.33 / 0.71 / 5 / -579.425143 / 2.40 / -579.471209 / 2.21
8 / Cmpd_D_BAa1 / -579.435796 / 2.33 / 0.71 / ##### / ####
9 / Cmpd_C_BBa / -579.435704 / 2.39 / 2.39 / 6 / -579.425291 / 2.31 / -579.470896 / 2.41
10 / Cmpd_C_ABa / -579.435703 / 2.39 / 2.39 / ##### / ####
11 / Cmpd_D_BBb2 / -579.435598 / 2.46 / 0.84 / 7 / -579.425501 / 2.17 / -579.470215 / 2.83
12 / Cmpd_D_CBb2 / -579.435596 / 2.46 / 0.84 / ##### / ####
13 / Cmpd_D_ABb1 / -579.435464 / 2.54 / 0.92 / 8 / -579.425432 / 2.22 / -579.469994 / 2.97
14 / Cmpd_D_BAa2 / -579.435170 / 2.73 / 1.11 / 9 / -579.424477 / 2.82 / -579.470688 / 2.54
15 / Cmpd_D_CAa2 / -579.435168 / 2.73 / 1.11 / ##### / ####
16 / Cmpd_D_AAa2 / -579.434421 / 3.20 / 1.58 / 10 / -579.423845 / 3.21 / -579.469693 / 3.16
17 / Cmpd_A_AAb1 / -579.433130 / 4.01 / 0.00 / 11 / -579.422869 / 3.83 / -579.468270 / 4.05
18 / Cmpd_A_BAb1 / -579.433127 / 4.01 / 0.00 / ##### / ####
19 / Cmpd_C_CBb / -579.432741 / 4.25 / 4.25 / 12 / -579.422538 / 4.03 / -579.467637 / 4.45
20 / Cmpd_C_AAb / -579.431562 / 4.99 / 4.99 / 13 / -579.421119 / 4.92 / -579.466606 / 5.10
21 / Cmpd_C_BAb / -579.431561 / 4.99 / 4.99 / ##### / ####
22 / Cmpd_C_CAa / -579.430801 / 5.47 / 5.47 / 14 / -579.420075 / 5.58 / -579.466590 / 5.11
23 / Cmpd_D_ABa1 / -579.429687 / 6.17 / 4.55 / 15 / -579.419280 / 6.08 / -579.465015 / 6.10
24 / Cmpd_D_BBa1 / -579.429687 / 6.17 / 4.55 / ##### / ####
25 / Cmpd_D_CBa1 / -579.429408 / 6.34 / 4.72 / 16 / -579.419019 / 6.24 / -579.464729 / 6.28
26 / Cmpd_D_BBa2 / -579.428746 / 6.76 / 5.14 / 17 / -579.418317 / 6.68 / -579.464131 / 6.65
27 / Cmpd_D_CBa2 / -579.428746 / 6.76 / 5.14 / ##### / ####
28 / Cmpd_A_ABb1 / -579.428675 / 6.80 / 2.80 / 18 / -579.418559 / 6.53 / -579.463914 / 6.79
29 / Cmpd_A_BBb1 / -579.428675 / 6.80 / 2.80 / ##### / ####
30 / Cmpd_D_AAb1 / -579.428072 / 7.18 / 5.56 / 19 / -579.417636 / 7.11 / -579.463089 / 7.31
31 / Cmpd_D_ABa2 / -579.427785 / 7.36 / 5.74 / 20 / -579.417316 / 7.31 / -579.463290 / 7.18
32 / Cmpd_D_BAb1 / -579.427773 / 7.37 / 5.75 / 21 / -579.417272 / 7.34 / -579.462895 / 7.43
33 / Cmpd_D_CAb1 / -579.427773 / 7.37 / 5.75 / ##### / ####
34 / Cmpd_D_BAb2 / -579.427639 / 7.45 / 5.83 / 22 / -579.417105 / 7.44 / -579.462846 / 7.46
35 / Cmpd_D_CAb2 / -579.427639 / 7.45 / 5.83 / ##### / ####
36 / Cmpd_D_AAb2 / -579.426038 / 8.46 / 6.84 / 23 / -579.415551 / 8.42 / -579.461155 / 8.52
37 / Cmpd_A_BBb2 / -579.425534 / 8.77 / 4.77 / 24 / -579.415631 / 8.37 / -579.460379 / 9.01
38 / Cmpd_A_CBb2 / -579.425534 / 8.77 / 4.77 / ##### / ####
39 / Cmpd_A_BAb2 / -579.425481 / 8.81 / 4.80 / 25 / -579.415343 / 8.55 / -579.460447 / 8.96
40 / Cmpd_A_AAb2 / -579.425480 / 8.81 / 4.80 / ##### / ####
41 / Cmpd_C_CBa / -579.425198 / 8.99 / 8.99 / 26 / -579.414664 / 8.97 / -579.461058 / 8.58
42 / Cmpd_A_AAa1 / -579.424752 / 9.27 / 5.26 / 27 / -579.414453 / 9.11 / -579.459958 / 9.27
43 / Cmpd_A_BAa1 / -579.424751 / 9.27 / 5.26 / ##### / ####
44 / Cmpd_A_CAb1 / -579.422394 / 10.74 / 6.74 / 28 / -579.411939 / 10.68 / -579.458204 / 10.37
45 / Cmpd_C_CAb / -579.421051 / 11.59 / 11.59 / 29 / -579.410441 / 11.62 / -579.456528 / 11.42
46 / Cmpd_A_ABa1 / -579.420435 / 11.97 / 7.97 / 30 / -579.410268 / 11.73 / -579.455763 / 11.90
47 / Cmpd_A_ABa2 / -579.420434 / 11.97 / 7.97 / ##### / ####
48 / Cmpd_A_BBa1 / -579.420434 / 11.97 / 7.97 / ##### / ####
49 / Cmpd_C_BBb / -579.419639 / 12.47 / 12.47 / 31 / -579.409195 / 12.41 / -579.454847 / 12.48
50 / Cmpd_C_ABb / -579.419638 / 12.47 / 12.47 / ##### / ####
51 / Cmpd_A_BBa2 / -579.418963 / 12.90 / 8.89 / 32 / -579.409040 / 12.50 / -579.453811 / 13.13
52 / Cmpd_A_CBa2 / -579.418963 / 12.90 / 8.89 / ##### / ####
53 / Cmpd_A_AAa2 / -579.417493 / 13.82 / 9.81 / 33 / -579.407325 / 13.58 / -579.452512 / 13.94
54 / Cmpd_A_BAa2 / -579.417493 / 13.82 / 9.81 / ##### / ####
55 / Cmpd_A_CBb1 / -579.417287 / 13.95 / 9.94 / 34 / -579.406994 / 13.79 / -579.453286 / 13.46
56 / Cmpd_A_CAa1 / -579.413057 / 16.60 / 12.60 / 35 / -579.402543 / 16.58 / -579.448990 / 16.15
57 / Cmpd_A_CAb2 / -579.412262 / 17.10 / 13.09 / 36 / -579.401832 / 17.03 / -579.448021 / 16.76
58 / Cmpd_A_ABb2 / -579.412017 / 17.26 / 13.25 / 37 / -579.401783 / 17.06 / -579.447317 / 17.20
59 / Cmpd_B_CAb21 / -579.410964 / 17.92 / 0.00 / 38 / -579.401224 / 17.41 / -579.445420 / 18.39
60 / Cmpd_B_ABb22 / -579.410389 / 18.28 / 0.36 / 39 / -579.400143 / 18.09 / -579.445451 / 18.37
61 / Cmpd_B_BBb22 / -579.410388 / 18.28 / 0.36 / ##### / ####
62 / Cmpd_B_CBb22 / -579.407948 / 19.81 / 1.89 / ##### / ####
63 / Cmpd_A_CBa1 / -579.407857 / 19.87 / 15.86 / ##### / ####
64 / Cmpd_B_AAb21 / -579.407077 / 20.36 / 2.44 / ##### / ####
65 / Cmpd_B_BAb21 / -579.407077 / 20.36 / 2.44 / ##### / ####
66 / Cmpd_B_BBb21 / -579.402787 / 23.05 / 5.13 / ##### / ####
67 / Cmpd_B_ABb21 / -579.402782 / 23.05 / 5.13 / ##### / ####
68 / Cmpd_B_AAb22 / -579.402675 / 23.12 / 5.20 / ##### / ####
69 / Cmpd_B_BAb22 / -579.402672 / 23.12 / 5.20 / ##### / ####
70 / Cmpd_A_CAa2 / -579.402602 / 23.16 / 19.16 / ##### / ####
71 / Cmpd_B_CAb22 / -579.402271 / 23.37 / 5.45 / ##### / ####
72 / Cmpd_B_CAa21 / -579.402103 / 23.48 / 5.56 / ##### / ####
73 / Cmpd_B_ABa22 / -579.399926 / 24.84 / 6.93 / ##### / ####
74 / Cmpd_B_BBa22 / -579.399926 / 24.84 / 6.93 / ##### / ####
75 / Cmpd_B_CBb21 / -579.399566 / 25.07 / 7.15 / ##### / ####
76 / Cmpd_B_CAb11 / -579.398455 / 25.77 / 7.85 / ##### / ####
77 / Cmpd_B_ABb12 / -579.397239 / 26.53 / 8.61 / ##### / ####
78 / Cmpd_B_BBb12 / -579.397239 / 26.53 / 8.61 / ##### / ####
79 / Cmpd_B_BAb11 / -579.396838 / 26.78 / 8.86 / ##### / ####
80 / Cmpd_B_AAb11 / -579.396837 / 26.78 / 8.86 / ##### / ####
81 / Cmpd_B_CBa22 / -579.396616 / 26.92 / 9.00 / ##### / ####
82 / Cmpd_B_AAa21 / -579.395978 / 27.32 / 9.40 / ##### / ####
83 / Cmpd_B_BAa21 / -579.395977 / 27.32 / 9.40 / ##### / ####
84 / Cmpd_B_CBb12 / -579.395776 / 27.45 / 9.53 / ##### / ####
85 / Cmpd_B_ABa21 / -579.392692 / 29.38 / 11.47 / ##### / ####
86 / Cmpd_B_BBa21 / -579.392692 / 29.38 / 11.47 / ##### / ####
87 / Cmpd_B_AAa22 / -579.392229 / 29.67 / 11.76 / ##### / ####
88 / Cmpd_B_BAa22 / -579.392229 / 29.67 / 11.76 / ##### / ####
89 / Cmpd_B_CAa22 / -579.390818 / 30.56 / 12.64 / ##### / ####
90 / Cmpd_B_CAb12 / -579.390130 / 30.99 / 13.07 / ##### / ####
91 / Cmpd_B_AAb12 / -579.389241 / 31.55 / 13.63 / ##### / ####
92 / Cmpd_B_BAb12 / -579.389241 / 31.55 / 13.63 / ##### / ####
93 / Cmpd_B_ABb11 / -579.389105 / 31.63 / 13.72 / ##### / ####
94 / Cmpd_B_BBb11 / -579.389103 / 31.63 / 13.72 / ##### / ####
95 / Cmpd_B_CAa11 / -579.388085 / 32.27 / 14.36 / ##### / ####
96 / Cmpd_B_CBb11 / -579.387860 / 32.41 / 14.50 / ##### / ####
97 / Cmpd_B_CBa21 / -579.387857 / 32.42 / 14.50 / ##### / ####
98 / Cmpd_B_ABa12 / -579.385267 / 34.04 / 16.12 / ##### / ####
99 / Cmpd_B_BBa12 / -579.385265 / 34.04 / 16.13 / ##### / ####
100 / Cmpd_B_BAa11 / -579.384160 / 34.74 / 16.82 / ##### / ####
101 / Cmpd_B_AAa11 / -579.384159 / 34.74 / 16.82 / ##### / ####
102 / Cmpd_B_CBa12 / -579.383038 / 35.44 / 17.52 / ##### / ####
103 / Cmpd_B_ABa11 / -579.377545 / 38.89 / 20.97 / ##### / ####
104 / Cmpd_B_BBa11 / -579.377545 / 38.89 / 20.97 / ##### / ####
105 / Cmpd_B_AAa12 / -579.377375 / 38.99 / 21.08 / ##### / ####
106 / Cmpd_B_BAa12 / -579.377375 / 38.99 / 21.08 / ##### / ####
107 / Cmpd_B_CAa12 / -579.377298 / 39.04 / 21.13 / ##### / ####
108 / Cmpd_B_CBa11 / -579.374739 / 40.65 / 22.73 / ##### / ####
Table S2. The optimized monoxime structures up to +19 kcal/mol from the global minimum. The ranking order and the relative energies (reported to the global minimum and then to each compound minimum) are presented:
01-Cmpd_C_AAa 0.00 0.00 /
02-Cmpd_D_ABb2 +1.62 0.00 /
03-Cmpd_D_BBb1 +1.90 +0.27
04-Cmpd_D_AAa1 +2.18 +0.56 /
05-Cmpd_D_CAa1 +2.33 +0.71 /
06-Cmpd_C_BBa +2.39 +2.39
07-Cmpd_D_BBb2 +2.46 +0.84 /
08-Cmpd_D_ABb1 +2.54 +0.92 /
09-Cmpd_D_BAa2 +2.73 +1.11
10-Cmpd_D_AAa2 +3.20 +1.58 /
11-Cmpd_A_AAb1 +4.01 0.00 /
12-Cmpd_C_CBb +4.25 +4.25
13-Cmpd_C_AAb +4.99 +4.99 /
14-Cmpd_C_CAa +5.47 +5.47 /
15-Cmpd_D_ABa1 +6.17 +4.55
16-Cmpd_D_CBa1 +6.34 +4.72 /
17-Cmpd_D_BBa2 +6.76 +5.14 /
18-Cmpd_A_ABb1 +6.80 +2.80
19-Cmpd_D_AAb1 +7.18 +5.56 /
20-Cmpd_D_ABa2 +7.36 +5.74 /
21-Cmpd_D_BAb1 +7.37 5.75
22-Cmpd_D_BAb2 +7.45 +5.83 /
23-Cmpd_D_AAb2 +8.46 +6.84 /
24-Cmpd_A_BBb2 +8.77 +4.77
25-Cmpd_A_BAb2 +8.81 +4.80 /
26-Cmpd_C_CBa +8.99 +8.99 /
27-Cmpd_A_AAa1 +9.27 +5.26
28-Cmpd_A_CAb1 +10.74 +6.74 /
29-Cmpd_C_CAb1 +11.59 +11.59 /
30-Cmpd_A_ABa1 +11.97 +7.97
31-Cmpd_C_BBb +12.47 +12.47 /
32-Cmpd_A_BBa2 +12.9 +8.89 /
33-Cmpd_A_AAa2 +13.82 +9.81
34-Cmpd_A_CBb1 +13.95 +9.94 /
35-Cmpd_A_CAa +16.60 +12.60 /
36-Cmpd_A_CAb2 +17.10 +13.09
37-Cmpd_A_ABb2 +17.26 +13.25 /
38-Cmpd_B_CAb21 +17.92 0.00 /
39-Cmpd_B_ABb22 +18.28 +0.36
Table S3. Energy ranking for all of the dioxime computed structures.
Nr / Cmpd / Zpcorr Energy / Dgl / D cm / Rank / Enthalpy / DH / Free Energy / DG1 / Cmpd_OH_A_BAa1a / -654.596012 / 0.00 / 0.00 / 1 / -654.584659 / 0.00 / -654.632466 / 0.00
2 / Cmpd_OH_A_AAa1a / -654.596011 / 0.00 / 0.00 / ######## / #####
3 / Cmpd_OH_A_BAa1b / -654.596010 / 0.00 / 0.00 / ######## / #####
4 / Cmpd_OH_A_AAa1b / -654.596009 / 0.00 / 0.00 / ######## / #####
5 / Cmpd_OH_A_ABa1a / -654.591922 / 2.57 / 2.57 / 2 / -654.580676 / 2.50 / -654.628305 / 2.61
6 / Cmpd_OH_A_ABa1b / -654.591922 / 2.57 / 2.57 / ######## / #####
7 / Cmpd_OH_A_BBa1b / -654.591921 / 2.57 / 2.57 / ######## / #####
8 / Cmpd_OH_A_BBa1a / -654.591920 / 2.57 / 2.57 / ######## / #####
9 / Cmpd_OH_A_AAb1a / -654.590227 / 3.63 / 3.63 / 3 / -654.578883 / 3.62 / -654.626807 / 3.55
10 / Cmpd_OH_A_BAb1a / -654.590226 / 3.63 / 3.63 / ######## / #####
11 / Cmpd_OH_A_CBa2b / -654.589320 / 4.20 / 4.20 / 4 / -654.578240 / 4.03 / -654.625505 / 4.37
12 / Cmpd_OH_A_CBa2a / -654.589319 / 4.20 / 4.20 / ######## / #####
13 / Cmpd_OH_A_BBa2b / -654.589318 / 4.20 / 4.20 / ######## / #####
14 / Cmpd_OH_A_BBa2a / -654.589317 / 4.20 / 4.20 / ######## / #####
15 / Cmpd_OH_C_AAaa / -654.589285 / 4.22 / 0.00 / 5 / -654.577819 / 4.29 / -654.625734 / 4.22
16 / Cmpd_OH_C_BAaa_r-202 / -654.589284 / 4.22 / 0.00 / ######## / #####
17 / Cmpd_OH_C_AAab / -654.589282 / 4.22 / 0.00 / ######## / #####
18 / Cmpd_OH_C_BAab / -654.589280 / 4.22 / 0.00 / ######## / #####
19 / Cmpd_OH_A_AAb1b / -654.589272 / 4.23 / 4.23 / 6 / -654.577704 / 4.36 / -654.62612 / 3.98
20 / Cmpd_OH_A_BAb1b / -654.589272 / 4.23 / 4.23 / ######## / #####
21 / Cmpd_OH_A_AAa2a / -654.588704 / 4.59 / 4.59 / 7 / -654.577426 / 4.54 / -654.625061 / 4.65
22 / Cmpd_OH_A_BAa2a / -654.588704 / 4.59 / 4.59 / ######## / #####
23 / Cmpd_OH_A_AAa2b / -654.588702 / 4.59 / 4.59 / ######## / #####
24 / Cmpd_OH_A_BAa2b / -654.588699 / 4.59 / 4.59 / ######## / #####
25 / Cmpd_OH_A_ABb1a / -654.585801 / 6.41 / 6.41 / 8 / -654.574593 / 6.32 / -654.622472 / 6.27
26 / Cmpd_OH_A_ABb2a / -654.585799 / 6.41 / 6.41 / ######## / #####
27 / Cmpd_OH_A_BBb1a / -654.585799 / 6.41 / 6.41 / ######## / #####
28 / Cmpd_OH_C_ABba / -654.585422 / 6.64 / 2.42 / 9 / -654.574120 / 6.61 / -654.621756 / 6.72
29 / Cmpd_OH_C_ABaa / -654.585421 / 6.65 / 2.42 / ######## / #####