Assessment of Gaussian-4 theory for the computation of enthalpies of formation of large organic molecules

Olga V. Dorofeeva, Inna N. Kolesnikova, Ilya I. Marochkin, Oxana N. Ryzhova

Supporting Information

The G4(0) electronic energies, ZPE and thermal corrections, symmetry and relative energies of low-lying stable conformers for all 122 molecules studied in this work.

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Number Symmetry of most
№ Compound Formula of non- G4(0) ZPE H(298)-H(0) stable conformers and
hydrogen hartree hartree hartree energies of other
atoms stable conformers
1 Nitroethane C2H5NO2 5 -284.194282 0.077277 0.006430 Cs
2 1,2-Dinitroethane C2H4N2O4 8 -488.641913 0.080489 0.008797 C2
3 Tetranitromethane CN4O8 13 -858.200337 0.054785 0.012535 S4
4 N,N-Dinitromethanamine CH3N3O4 8 -504.628417 0.067524 0.008594 C1
5 N-Nitrodimethylamine C2H6N2O2 6 -339.491482 0.093583 0.007743 Cs
6 Nitrobenzene C6H5NO2 9 -436.551630 0.101631 0.007788 C2v
7 2-Chloronitrobenzene C6H4ClNO2 10 -896.031079 0.091912 0.009043 C1
8 3-Chloronitrobenzene C6H4ClNO2 10 -896.039970 0.092101 0.008997 Cs
9 4-Chloronitrobenzene C6H4ClNO2 10 -896.040653 0.092151 0.008997 C2v
10 2,4-Dichloronitrobenzene C6H3Cl2NO2 11 -1355.519062 0.082376 0.010285 C1
11 2,5-Dichloronitrobenzene C6H3Cl2NO2 11 -1355.518453 0.082355 0.010299 C1
12 3,4-Dichloronitrobenzene C6H3Cl2NO2 11 -1355.526286 0.082619 0.010210 Cs
13 3,5-Dichloronitrobenzene C6H3Cl2NO2 11 -1355.527412 0.082506 0.010260 C2v
14 2,4,6-Trichloronitrobenzene C6H2Cl3NO2 12 -1815.003998 0.072507 0.011785 C2v
15 2,3,5,6-Tetrachloronitrobenzene C6HCl4NO2 13 -2274.487768 0.062952 0.013069 C2v
16 Pentachloronitrobenzene C6Cl5NO2 14 -2733.969989 0.053370 0.014307 C2v
17 2-Chloro-4-nitrophenol C6H4ClNO3 11 -971.249056 0.096622 0.010057 Cs
18 4-Chloro-2-nitrophenol C6H4ClNO3 11 -971.249262 0.096847 0.009765 Cs
19 4-Chloro-3-nitrophenol C6H4ClNO3 11 -971.235426 0.096118 0.010244 C1
20 4,5-Dichloro-2-nitroaniline C6H4Cl2N2O2 12 -1410.862518 0.098666 0.011932 Cs
21 2,5-Dichloro-4-nitroaniline C6H4Cl2N2O2 12 -1410.856464 0.098843 0.011828 C1
22 2,6-Dichloro-4-nitroaniline C6H4Cl2N2O2 12 -1410.868185 0.099090 0.011772 C1
23 2-Methoxy-5-nitrophenol C7H7NO4 12 -626.228278 0.138140 0.011530 Cs
24 4-Methoxy-2-nitrophenol C7H7NO4 12 -626.228634 0.138202 0.011156 Cs 6.0 (C1)
25 1H-Pyrazole C3H4N2 5 -226.082563 0.070242 0.004716 Cs
26 1-Methylpyrazole C4H6N2 6 -265.358928 0.097336 0.006404 C1
27 1H-Imidazole C3H4N2 5 -226.100072 0.070109 0.004737 Cs
28 1-Methylimidazole C4H6N2 6 -265.373643 0.097422 0.006383 Cs
29 1H-1,2,4-Triazole C2H3N3 5 -242.141644 0.059036 0.004522 Cs
30 1-Methyl-1H-tetrazole C2H4N4 6 -297.430083 0.073543 0.006207 Cs
31 2-Methyl-2H-tetrazole C2H4N4 6 -297.436091 0.074200 0.006145 Cs
32 5-Methyl-1H-tetrazole C2H4N4 6 -297.441181 0.073552 0.006145 Cs
33 Imidazolidin-2-one C3H6N2O 6 -302.519740 0.098578 0.006152 C2
34 Parabanic acid C3H2N2O3 8 -450.580046 0.061168 0.007233 C2v
35 2,3-Dihydroxypyridine C5H5NO2 8 -398.563360 0.096479 0.007335 Cs
36 2-Acetylpyridine C7H7NO 9 -400.718584 0.123810 0.008812 Cs
37 4-Acetylpyridine C7H7NO 9 -400.714166 0.124033 0.008735 Cs
38 Pyridazine C4H4N2 6 -264.148800 0.074996 0.005217 C2v
39 2-Chloropyrimidine C4H3ClN2 7 -723.674837 0.066179 0.006234 C2v
40 2,4-Dichloropyrimidine C4H2Cl2N2 8 -1183.166112 0.056649 0.007379 Cs
41 4,6-Dichloropyrimidine C4H2Cl2N2 8 -1183.167516 0.056857 0.007380 C2v
42 2,4,6-Trichloropyrimidine C4HCl3N2 9 -1642.656662 0.047054 0.008584 C2v
43 2,4,5,6-Tetrachloropyrimidine C4Cl4N2 10 -2102.139106 0.037541 0.009797 C2v
44 2-Chloropyrazine C4H3ClN2 7 -723.668212 0.066129 0.006249 Cs
45 2,6-Dichloropyrazine C4H2Cl2N2 8 -1183.158332 0.056548 0.007414 C2v
46 1,3,5-Triazine C3H3N3 6 -280.234348 0.064293 0.005094 D3h
47 N,N'-Trimethyleneurea C4H8N2O 7 -341.801352 0.126997 0.007436 Cs 13.0 (C1)
48 Barbituric acid C4H4N2O3 9 -489.873828 0.089731 0.008488 C2v
49 5,5-Dimethylbarbituric acid C6H8N2O3 11 -568.439263 0.145127 0.011311 C2v
50 Barbital C8H12N2O3 13 -646.986507 0.201026 0.014159 C2v 5.1 (C1), 13.8 (C2)
51 Indole C8H7N 9 -363.609508 0.127456 0.007354 Cs
52 5-Nitroindole C8H6N2O2 12 -568.069972 0.130404 0.009792 Cs
53 Oxindole C8H7NO 10 -438.835129 0.131669 0.008400 Cs
54 1H-Benzotriazole C6H5N3 9 -395.673809 0.104363 0.006937 Cs
55 2,3-Dichloroquinoxaline C8H4Cl2N2 12 -1336.723585 0.102405 0.010022 C2v
56 Caffeine C8H10N4O2 14 -680.048571 0.188358 0.014239 Cs 0.2 (Cs)
57 1-(2-nitrophenyl)pyrrole C10H8N2O2 14 -645.408914 0.162783 0.011965 C1 3.4 (C1)
58 1-(4-nitrophenyl)pyrrole C10H8N2O2 14 -645.418208 0.163357 0.011812 C2
59 N-Methylcarbazole C13H11N 14 -556.453811 0.200979 0.011673 Cs
60 Phenazine C12H8N2 14 -571.301327 0.167320 0.010216 D2h
61 Oxazole C3H3NO 5 -245.960224 0.057751 0.004513 Cs
62 Isoxazole C3H3NO 5 -245.923522 0.057166 0.004543 Cs
63 1,3-Oxazolidine-2-thione C3H5NOS 6 -645.236719 0.083672 0.006440 C1
64 1,3-Thiazolidine-2-thione C3H5NS2 6 -968.116530 0.080376 0.006879 C1
65 2-Thiopheneacetic acid C6H6O2S 9 -780.595313 0.108245 0.009347 C1 1.0 (C1), 1.3 (C1)
66 3-Thiopheneacetic acid C6H6O2S 9 -780.596553 0.108294 0.009338 C1 0.8 (C1), 1.0 (C1)
67 2,5-Thiophenedicarboxylic acid C6H4O4S 11 -929.846023 0.095556 0.010790 C2v 0.5 (Cs), 1.5 (C2v)
68 2,2′-Bithiophene C8H6S2 10 -1104.417902 0.112236 0.009417 C2
69 3,3′-Bithiophene C8H6S2 10 -1104.418108 0.112295 0.009362 C2
70 5-Methyl-1,3-benzodioxole C8H8O2 10 -459.852419 0.141056 0.009401 C1
71 5-Nitro-1,3-benzodioxole C7H5NO4 12 -625.027504 0.116879 0.010110 Cs
72 5-Cyano-1,3-benzodioxole C8H5NO2 11 -512.795932 0.112840 0.009418 Cs
73 Benzoxazole C7H5NO 9 -399.527786 0.104188 0.006781 Cs
74 Anthranil C7H5NO 9 -399.469499 0.103316 0.006905 Cs
75 3H-1,3-Benzoxazole-2-thione C7H5NOS 10 -797.611200 0.106601 0.008265 Cs
76 Benzothiazole C7H5NS 9 -722.411694 0.100856 0.007322 Cs
77 3H-1,3-Benzthiazole-2-thione C7H5NS2 10 -1120.496158 0.103604 0.008842 Cs
78 Chromanone C9H8O2 11 -497.963017 0.148227 0.009268 C1
79 Dibenzofuran C12H8O 13 -537.041407 0.161512 0.009583 C2v
80 Dibenzothiophene C12H8S 13 -859.929942 0.158493 0.010207 C2v
81 1,2,3,4-tetrahydrodibenzothiophene C12H12S 13 -862.301561 0.204066 0.011307 C1
82 4-Methyldibenzothiophene C13H10S 14 -899.216046 0.185453 0.011986 Cs
83 Dibenzo-p-dioxin C12H8O2 14 -612.219905 0.165154 0.010664 D2h
84 2-Chlorodibenzo-p-dioxin C12H7ClO2 15 -1071.709333 0.155729 0.011933 Cs
85 1,2-Dimethylbenzene C8H10 8 -310.660454 0.153062 0.008597 C2v
86 1,3-Dimethylbenzene C8H10 8 -310.660788 0.152331 0.007370 C2v
87 1,4-Dimethylbenzene C8H10 8 -310.660421 0.152399 0.009153 C2h
88 Ethylbenzene C8H10 8 -310.655777 0.153969 0.008388 Cs 4.4 (Cs)
89 Norbornane C7H12 7 -273.745607 0.174101 0.006648 C2v
90 Cyclopropylbenzene C9H10 9 -348.712588 0.160053 0.008502 Cs 3.6 (Cs)
91 Diphenylmethane C13H12 13 -502.295920 0.206102 0.011382 C2
92 Dipropyl ether C6H14O 7 -312.037517 0.190392 0.010398 C2 0.4 (Cs), 0.8 (C1), 1.6 (C2v), 5.3 (C1), 5.6 (C1), 6.3 (C1), 6.4 (C1), 7.2 (C1)
93 tert-Amyl methyl ether C6H14O 7 -312.041700 0.189029 0.010534 C1 0.1 (C1), 2.8 (Cs), 3.8 (C1), 11.6 (C1), 11.8 (C1)
94 Di-tert-butyl ether C8H18O 9 -390.606416 0.243767 0.012871 C2
95 Methoxybenzene C7H8O 8 -346.562138 0.130837 0.007885 Cs
96 2-Methoxyphenol C7H8O2 9 -421.769670 0.135333 0.009034 Cs
97 1,2-Dimethoxybenzene C8H10O2 10 -461.025454 0.162809 0.010478 C2v 4.6 (C1), 8.6 (C2)
98 1,3-Dimethoxybenzene C8H10O2 10 -461.031062 0.162847 0.010474 Cs 2.0 (C2v), 2.5 (C2v)
99 Triethylamine C6H15N 7 -292.158135 0.201964 0.010581 C3 0.1 (C1), 2.8 (Cs)
100 4-Aminotoluene C7H9N 8 -326.709780 0.141944 0.008740 Cs
101 Aminoadamantane C10H17N 11 -445.755418 0.255380 0.009525 Cs
102 1,1,1-Tricyanoethane C5H3N3 8 -356.373474 0.069748 0.009012 C3v
103 Tetracyanomethane C5N4 9 -409.278496 0.040159 0.009414 Td
104 Cyanobenzene C7H5N 8 -324.320133 0.097577 0.007106 C2v
105 Benzamide C7H7NO 9 -400.742536 0.125608 0.008527 C1
106 (E)-1,2-Diphenyldiazene C12H10N2 14 -572.437728 0.187522 0.011931 C2h
107 Leucine C6H13NO2 9 -441.423735 0.189861 0.012025 C1 25 stable conformers with E<20 kJ/mol
108 Methionine C5H11NO2S 9 -800.213234 0.163100 0.012318 C1 46 stable conformers with E<20 kJ/mol
109 Proline C5H9NO2 8 -400.945748 0.142917 0.008241 C1 10 stable conformers with E<20 kJ/mol
110 α-Phenylglycine C8H9NO2 11 -515.223400 0.158460 0.010971 C1 13 stable conformers with E<20 kJ/mol
111 Phenylalanine C9H11NO2 12 -554.506159 0.187399 0.011728 C1 20 stable conformers with E<20 kJ/mol
112 1,2-Dichlorobenzene C6H4Cl2 8 -1151.071798 0.080070 0.007667 C2v
113 1,3-Dichlorobenzene C6H4Cl2 8 -1151.074157 0.080050 0.007667 C2v
114 1,4-Dichlorobenzene C6H4Cl2 8 -1151.073874 0.080050 0.007703 D2h
115 1,2,3,4-Tetrachlorobenzene C6H2Cl4 10 -2070.043918 0.061109 0.010108 C2v
116 1,2,3,5-Tetrachlorobenzene C6H2Cl4 10 -2070.046489 0.061094 0.010145 C2v
117 1,2,4,5-Tetrachlorobenzene C6H2Cl4 10 -2070.046183 0.061137 0.010149 D2h
118 Pentachlorobenzene C6HCl5 11 -2529.529309 0.053370 0.011375 C2v
119 2-Chlorobenzoic acid C7H5ClO2 10 -880.103648 0.104182 0.009407 C1 1.1 (C1)
120 3-Chlorobenzoic acid C7H5ClO2 10 -880.111561 0.104346 0.009344 Cs 0.2 (Cs)
121 4-Chlorobenzoic acid C7H5ClO2 10 -880.112203 0.104394 0.009333 Cs
122 3,5-Dichloroanisole C7H6Cl2O 10 -1265.542540 0.112041 0.010319 Cs

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