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Supporting Information Reply to Comment on Estimated Gas-Phase Standard State Enthalpies of Formation for Organic Compounds Using the Gaussian-4 (G4) and W1BD Theoretical Methods Sierra Rayne*, and Kaya Forest Ecologica Research, Kelowna, British Columbia, Canada V1Y 1R9; Department of Chemistry, Okanagan College, Penticton, British Columbia, Canada V2A 8E1 * Corresponding author. E-mail: rayne.sierra@gmail.com. Ecologica Research. Okanagan College. S1

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Kormos, B. L.; Liebman, J. F.; Cramer, C. J. 298 K enthalpies of formation of monofluorinated alkanes: Theoretical predictions for methyl, ethyl, isopropyl and tert-butyl fluoride. J. Phys. Org. Chem. 2004, 17, 656-664. Lazarou, Y. G.; Prosmitis, A. V.; Papadimitriou, V. C.; Papagiannakopoulous, P. Theoretical calculation of bond dissociation energies and enthalpies of formation for halogenated molecules. J. Phys. Chem. A 2001, 105, 6729-6742. Li, H. X.; Zhang, R. Z.; Yang, X. D.; Zhang, H. Density functional studies of the heats of formation of several nitroester compounds. J. Mol. Struct. (Theochem) 2007, 815, 151-156. Liu, M. H.; Chen, C.; Liu, C. W.; Hong, Y. S. Theoretical study on thermodynamic properties of C1-C16 alkanes: A 3-parameter least-squared calibration. J. Phys. Chem. A 2004, 108, 6784-6787. Matulis, V. E.; Ivashkevich, O. A.; Gaponik, P. N.; Elkind, P. D.; Sukhanov, G. T.; Bazyleva, A. B.; Zaitsau, D. H. Theoretical study of gas-phase formation enthalpies and isomerism for 4(5)-nitro-1,2,3-triazole and its N-alkyl derivatives and experimental determination of formation enthalpy for 2-methyl-4-nitro-1,2,3triazole. J. Mol. Struct. (Theochem) 2008, 854, 18-25. Mo, O.; Yanez, M.; Elguero, J.; Roux, M. V.; Jimenez, P.; Davalos, J. Z.; da Silva, M. A. V. R.; da Silva, M. D. D. M. C. R.; Cabildo, P.; Claramunt, R. Substituent effects on enthalpies of formation: Benzene derivatives. J. Phys. Chem. A 2003, 107, 366-371. Notario, R.; Castano, O.; Gomperts, R.; Frutos, L. M.; Palmeiro, R. Organic thermochemistry at high ab initio levels. 3. A G3 study of cyclic saturated and unsaturated hydrocarbons (including aromatics). J. Org. Chem. 2000, 65, 4298-4302. Novak, I.; Pratt, L. M. Computational study of lithioprismanes. Chem. Phys. Lett. 400, 2004, 558-562. Parthiban, S.; Martin, J. M. L. Assessment of W1 and W2 theories for the computation of electron affinities, ionization potentials, heats of formation, and proton affinities. J. Chem. Phys. 2001, 114, 6014-6029. Poutsma, J. C.; Schroeder, O. E.; Squires, R. R. Experimental chloride ion affinities and theoretical predictions for the absolute heats of formation of SiCl2 and SiClF. Chem. Phys. Lett. 2004, 389, 433-437. Sabbe, M. K.; Saeys, M.; Reyniers, M. F.; Marin, G. B.; van Speybroeck, V.; Waroquier, M. Group additive values for the gas phase standard enthalpy of formation of hydrocarbons and hydrocarbon radicals. J. Phys. Chem. A 2005, 109, 7466-7480. Sicre, J. E.; Cobos, C. J. Thermochemistry of the higher chlorine oxides ClOx (x=3,4) and Cl2Ox (x=3-7). J. Mol. Struct. (Theochem) 2003, 620, 215-226. Simmie, J. M.; Black, G.; Curran, H. J.; Hinde, J. P. Enthalpies of formation and bond dissociation energies of lower alkyl hydroperoxides and related hydroperoxy and alkoxy radicals. J. Phys. Chem. A 2008, 112, 5010-5016. Su, X.; Cheng, X.; Liu, Y.; Li, Q. Theoretical calculation of bond dissociation energies and heats of formation for nitromethane and polynitromethanes with density functional theory. Int. J. Quant. Chem. 2007, 107, 515-521. S3

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Table S1. Gas phase total energies at 0 K and enthalpies at 298.15 K for all compounds from ref. [1] at the G4 level of theory. compound chlorotrifluoromethane cyanogen chloride difluorodichloromethane phosgene fluorotrichloromethane tetrachloromethane carbonic difluoride tetrafluoromethane trichloromethane trifluoromethane hydrogen cyanide dichloromethane difluoromethane formaldehyde formic acid chloromethane methane methanol methanethiol methylamine carbon monoxide carbon dioxide carbon disulfide chlorotrifluoroethene tetrachloroethene trifluoroacetonitrile tetrafluoroethene trichloroethene trifluoroethene acetylene 1,1-dichloroethene cis-1,2-dichloroethene trans-1,2-dichloroethene 1,1-difluoroethene chloroethene 1,1,1-trichloroethane fluoroethene 1,1,1-trifluoroethane acetonitrile ethylene acetaldehyde ethylene oxide acetic acid ethane ethanol dimethyl sulfoxide dimethylamine propyne cyclopropene propene cyclopropane acetone oxetane S5 E0-797.637056-552.869940-1157.881521-1033.449616-1518.130334-1878.384330-312.943594-437.395959-1418.907239-338.154623-93.392736-959.426517-238.910265-114.453190-189.692991-499.944810-40.465305-115.651773-438.529305-95.778304-113.289426-188.535266-834.235285-835.666121-1916.462008-430.355386-475.402479-1456.980033-376.184346-77.290355-997.495731-997.496553-997.495829-276.976697-538.010543-1458.195076-177.746588-377.445972-132.683797-78.521873-153.743784-153.700317-228.982902-79.738111-154.934235-552.986068-135.046735-116.576743-116.538353-117.803881-117.790194-193.033145-192.980010 H298-797.631741-552.865765-1157.875761-1033.444690-1518.124129-1878.377674-312.939353-437.391064-1418.901777-338.150206-93.389268-959.421970-238.906193-114.449376-189.688872-499.940833-40.461490-115.647496-438.524737-95.773933-113.286121-188.531709-834.231249-835.659605-1916.454495-430.349330-475.396249-1456.973679-376.178897-77.286490-997.490468-997.491299-997.490320-276.972019-538.006038-1458.188160-177.742280-377.440160-132.679247-78.517874-153.738936-153.696203-228.977339-79.733661-154.928937-552.979400-135.041353-116.571771-116.534088-117.798825-117.785848-193.026763-192.974908

propylene oxide trimethylamine pyrazine pyrimidine pyridazine furan diketene thiophene pyrrole cyclopropanecarbonitrile cyclobutene methylenecyclopropane 1-methylcyclopropene bicyclo[1.1.0]butane cis-2-butene trans-2-butene 2-methyl-1-propene tetrahydrofuran butane isobutane pyridine bicyclo[1.1.0]butane-1-carbonitrile 1,3-cyclopentadiene 2-methyl-1-buten-3-yne cyclopropylacetylene bicyclo[2.1.0]pent-2-ene spiropentane bicyclo[2.1.0]pentane 1,1-dimethylcyclopropane pentane isopentane neopentane benzene fulvene 3,4-dimethylenecyclobut-1-ene tris(methylene)cyclopropane phenol aniline 2-methylpyridine bicyclo[2.1.0]pentane-1-carbonitrile hexane 2,2-dimethylbutane 2,3-dimethylbutane toluene 2,5-norbornadiene quadricyclane spiro[2,4]hepta-4,6-diene anti-tricyclo[3.2.0.02,4]hept-6-ene tetracyclo[4.1.0.02,4.03,5]heptane 1,2-bis(methylene)cyclobutane 3-methylenecyclopentene bicyclo[2.1.1]hex-2-ene bicyclo[2.2.0]hex-1(4)-ene benzyne phenylacetylene bicyclo[4.2.0]octa-1,3,5-triene 3,6-bis(methylene)-1,4-cyclohexadiene S6-192.986056-174.320274-264.177118-264.184175-264.148800-229.902630-305.102249-552.792971-210.044092-210.015692-155.854011-155.843071-155.825399-155.830849-157.083688-157.085722-157.087982-232.287981-158.293861-158.297011-248.137306-248.057828-193.969354-193.926192-193.909436-193.895999-195.115993-195.125904-196.355118-197.572048-197.574422-197.580466-232.093992-232.044651-231.998333-231.960240-307.299819-287.427285-287.423830-287.355669-236.850298-236.856654-236.853758-271.377407-271.304759-271.268362-271.310351-271.253901-271.255909-233.211920-233.248750-233.203105-233.145981-230.787514-308.216364-309.425442-309.417883-192.980657-174.313802-264.171963-264.179006-264.143583-229.897932-305.096107-552.787918-210.039125-210.009934-155.849212-155.837830-155.819675-155.826121-157.077201-157.079268-157.081679-232.282037-158.287090-158.290276-248.132047-248.051580-193.964214-193.919374-193.903271-193.890896-195.110067-195.120503-196.348155-197.563941-197.566343-197.572420-232.088591-232.038697-231.991811-231.953138-307.293306-287.420475-287.416758-287.348595-236.840848-236.847378-236.844357-271.370144-271.298869-271.262749-271.303503-271.247649-271.249970-233.204871-233.242167-233.197671-233.139463-230.781988-308.208840-309.418432-309.410135

1-cyclopropylpenta-1,3-diyne cyclopropylbenzenea trans-bicyclo[6.1.0]nona-2,4,6-triene cis-bicyclo[4.3.0]nona-3,7-diene octahydrodicyclopropa[cd,gh]pentalene (1α,2α,4α,5α)-tricyclo[3.2.1.02,4]oct-6-ene bicyclo[3.2.1]octa-2,6-diene 2,3-bis(methylene)bicyclo[2.2.0]hexane 7-methylenebicyclo[2.2.1]heptane anti-tricyclo[4.2.0.02,5]octane 1-propynylbenzene hexafluorobenzene 1,2,3-trichlorobenzene 1,2,4-trichlorobenzene 1,3,5-trichlorobenzene o-dichlorobenzene m-dichlorobenzene p-dichlorobenzene o-difluorobenzene m-difluorobenzene p-difluorobenzene chlorobenzene 1-buten-3-yne bicyclo[1.1.0]but-1(3)-ene (Z)-3-penten-1-yne (Z)-hexa-1,5-diyne-3-ene (E)-hexa-1,5-diyne-3-ene 1,2-bis(methylene)cyclobutane trans-2,3,4-hexatriene cis-2,3,4-hexatriene bicyclo[2.2.0]hexane 1,1-diethynylcyclopropane bicyclo[3.2.0]hepta-2,6-diene 3-methylene-1,4-cyclohexadiene 6-methylfulvene 2-norbornene nortricyclene tricyclo[4.1.0.02,4]heptane dispiro[2.0.2.1]heptane 5,5-dimethyl-1,3-cyclopentadiene tricyclo[4.1.0.02,7]heptane spiro[cyclopropane(1,5')bicyclo[2.1.0]pentane anti-tricyclo[4.1.0.02,4]heptane anti-tricyclo[3.2.0.02,4]heptane 3-(cis-ethylidene)-1-cyclopentene bicyclo[3.2.0]hept-1(5)-ene bicyclo[3.2.0]hept-1-ene styrene 5-(1-methylethylidene)-1,3-cyclopentadiene 2,3-dihydrothiophene 2,5-dihydrothiophene 1,3-dioxol-2-one cyclopropanone 1,3,5-trioxane carbon suboxide 4-methylene-2-oxetanone norbornan-7-one S7-309.321419-348.712594-348.641101-349.893549-310.598513-310.576670-310.609590-310.550296-311.812361-311.748297-347.502698-827.398115-1610.558402-1610.560542-1610.562734-1151.071801-1151.074140-1151.073883-430.539073-430.545037-430.543785-691.584550-154.642407-154.536018-193.926141-230.763494-230.763908-233.211920-233.194550-233.194521-234.405969-270.025792-271.296428-271.332604-271.328314-272.529374-272.533031-272.501576-272.443079-272.531230-272.486166-272.453861-272.501576-272.470142-272.529476-272.491500-272.495841-309.445516-310.612841-553.969548-553.968724-341.048817-191.777950-343.405165-264.630230-305.102249-347.754080-309.311500-348.704098-348.632600-349.884996-310.592165-310.570097-310.602636-310.541964-311.804612-311.740515-347.493270-827.387352-1610.549530-1610.551639-1610.553808-1151.064134-1151.066452-1151.066179-430.532097-430.538115-430.536846-691.578041-154.636915-154.531212-193.919293-230.756203-230.756440-233.204871-233.185978-233.185970-234.399409-270.017605-271.289964-271.325632-271.320803-272.523120-272.527130-272.494982-272.435315-272.523274-272.479552-272.446635-272.494982-272.463436-272.521233-272.484139-272.488875-309.437701-310.603726-553.963749-553.962859-341.043553-191.772981-343.399388-264.624653-305.096107-347.746566

2-propenenitrile 1,3,5-triazine 1H-imidazole 1H-pyrazole propiolonitrile 2-methyl-1H-imidazole 2-butynedinitrile 2,3-diazabicyclo[2.2.1]-hept-2-ene cyclobutadiene 1,2,3-butatriene methylenecyclopropene methylcyclopropane 1,3-pentadiyne penta-1,4-diyne 1,2,3,4-pentatetraene 1-penten-3-yne [1.1.1]propellane bicyclo[1.1.1]pentane 1-methylcyclobutene 3,3-dimethylcyclopropene 1,2-dimethylcyclopropene methylmethylenecyclopropane ethylidenecyclopropane hex-3-en-1,5-diyne 1,4-hexadiyne bicyclo[2.2.0]hexa-2,5-diene benzvalene 1-methyl-1,3-cyclopentadiene 5-methyl-1,3-cyclopentadiene bicyclo[2.2.0]hex-2-ene 1,3-bis(methylene)cyclobutane 2-methyl-1-penten-3-yne cyclopropylidene cyclopropane ethynylcyclobutane tricyclo[3.1.0.02,6]hexane bicyclo[2.1.1]hexane 1,3-dimethylbicyclo[1.1.0]butane 1,1-dimethyl-2-methylenecyclopropane 3,3-dimethylcyclobutene bicyclo[4.1.0]hepta-1,3,5-triene 5-ethenylidene-1,3-cyclopentadiene trans-1,2-diethynylcyclopropane bicyclo[3.2.0]hepta-1,4,6-triene cis-1,2-diethynylcyclopropane 5-methylenebicyclo[2.2.0]hex-2-ene spiro[3.3]hepta-2,5-diene tricyclo[4.1.0.02,7]hept-3-ene tricyclo[4.1.0.01,3]heptane tricyclo[3.1.1.03,6]heptane 1-methyl-1,2-propadienylcyclopropane cyclopentyl acetylene (1α,4α,5β)-5-methyl-2-methylenebicyclo[2.1.0]pentane endo-2-methylene-5-methylbicyclo[2.1.0]pentane 5,5-dimethylbicyclo[2.1.0]pent-2-ene syn-tricyclo[3.2.0.02,4]heptane bicyclo[4.2.0]octa-1,3,5,7-tetraene 2,4,6-octatriyne S8-170.746084-280.234365-226.100076-226.082554-169.510679-265.386966-261.726421-304.610935-154.588298-154.630310-154.604355-157.071408-192.700994-192.685383-192.687974-193.928556-193.884206-195.108770-195.140846-195.103507-195.111818-195.124627-195.125269-230.763909-231.971311-231.972585-231.979513-233.253631-233.248843-233.191764-233.207937-233.212257-233.163895-233.190511-233.203711-234.432532-234.398447-234.408704-234.420068-270.087380-270.098152-270.028196-270.062032-270.026666-271.262059-271.257907-271.277416-272.469198-272.471507-272.473284-272.498067-272.463349-272.477939-272.461337-272.455555-308.181591-308.113804-170.740978-280.229272-226.095337-226.077839-169.505708-265.380503-261.719903-304.604893-154.583532-154.624604-154.599350-157.065772-192.694201-192.678813-192.681356-193.921213-193.879234-195.103815-195.134505-195.096542-195.104510-195.117971-195.118534-230.756440-231.962897-231.967026-231.974222-233.246869-233.242316-233.185762-233.200851-233.203605-233.156843-233.183432-233.198041-234.426788-234.390698-234.400626-234.412531-270.081134-270.091126-270.020028-270.055800-270.018547-271.255116-271.250835-271.271148-272.462325-272.465264-272.464375-272.489813-272.455465-272.470146-272.453440-272.449013-308.174843-308.103310

(1α,2α,5α,6α)-tricyclo[4.2.0.02,5]octa-3,7-diene (1α,2β,5β,6α)-tricyclo[4.2.0.02,5]octa-3,7-diene bicyclo[2.2.2]octa-2,5,7-triene 2a,2b,4a,4b-tetrahydrocyclopropa[cd]pentalene pentacyclo[3.3.0.02,4.03,7.06,8]octane 7-methylenebicyclo[2.2.1]hepta-2,5-diene tricyclo[4.1.1.07,8]octa-2,4-diene cycloocta-1,5-dien-3-yne cycloocta-1,3-dien-6-yne 3-methylenetetracyclo[3.2.0.02,7.04,6]heptane 1,5-dihydropentalene 1-ethynyl-1-(1-propynyl)cyclopropane tetrakis(methylene)cyclobutane heptafulvene 5-methylenebicyclo[2.2.1]hept-2-ene 1,5-dimethyl-3-exo-methylenetricyclo[2.1.0.0]pentane tricyclo[4.1.1.07,8]oct-3-ene 1-methylnorbornadiene 2-methylnorbornadiene tricyclo[4.1.1.07,8]oct-2-ene 6-methyltricyclo[4.1.0.02,7]hept-3-ene 1-methyltricyclo[4.1.0.02,7]hept-3-ene 7-methylenebicyclo[3.2.0]hept-1-ene bicyclo[3.3.0]octa-2,6-diene 5-methyl-3H-1,2-dithiole-3-thione 4-methyl-3H-1,2-dithiole-3-thione dihydro-2(3h)-thiophenthione 2,2-dimethylthiirane 2-methylthietane 3-methylthietane 2-methyl-1,3-dithiacyclopentane 4-methyl-1,3-dithiolane 3-methyl-1,2-dithiolane 4-methyl-1,2-dithiolane trimethylthiirane 3,3-dimethylthietane 7-thiabicyclo[4.1.0]heptane 2-(1,1-dimethylethyl)thiirane thieno[3,2-b]thiophene thieno[2,3-b]thiophene thieno[3,4-b]thiophene dithio-p-benzoquinone benzodithiete methyl-oxirane cyclopropylidenemethanone 2(3H)-furanone 1,4-dioxin 3(2H)-furanone cyclobutane-1,3-dione 1,2-cyclobutanedione 2,5-dihydrofuran 2-methyl-1-propen-1-one 3-methyleneoxetane 4-methylene-1,3-dioxolane α-trimethylethylene oxide 7-oxabicyclo[2.2.1]heptane 2-oxaspiro[3,3]heptane S9-309.310455-309.320668-309.388729-309.385682-309.330918-309.370899-309.346573-309.349708-309.336736-309.338090-309.412548-309.311865-309.356319-309.400994-310.595196-310.507818-310.549631-310.589374-310.590608-310.550064-310.562966-310.562201-310.565851-310.616455-1348.948472-1348.949084-952.060394-555.165325-555.155925-555.154819-953.252208-953.251655-953.255358-953.253861-594.447686-594.439618-632.490462-633.723552-1027.052521-1027.049502-1027.045312-1027.014773-1027.038966-192.986057-229.850427-305.123861-305.060352-305.107732-305.098736-305.093519-231.078370-231.089683-231.046785-306.279011-271.557350-309.661372-309.610258-309.303510-309.313783-309.382194-309.379279-309.325241-309.363925-309.339613-309.341857-309.328607-309.331510-309.405498-309.301788-309.347513-309.393342-310.587845-310.498584-310.542144-310.581891-310.583069-310.542627-310.555165-310.554280-310.557924-310.609084-1348.939947-1348.940717-952.053441-555.158256-555.149239-555.148155-953.244311-953.243635-953.247290-953.245948-594.439069-594.431670-632.483093-633.713836-1027.045305-1027.042269-1027.038097-1027.006964-1027.031609-192.980657-229.844397-305.118140-305.054476-305.101988-305.092192-305.087005-231.072901-231.082632-231.040969-306.272650-271.548973-309.654894-309.602669

1,2,4-triazine 1,2,3-triazine 2-aziridinecarbonitrile 1-azetine cyclopropanimine dimethylcyanamide 3,3-dimethyldiazirine 1-pyrazoline 2-pyrazoline azetidine 1-methylaziridine 5-(dimethylamino)tetrazole 3,3-dimethyldiaziridine cyanoallene 1,1-dicyanoethane 3-methyl-1,2,4-triazine 6-methyl-1,2,4-triazine 4-methyl-1,2,3-triazine 4-aminopyrimidine 1-methyl-1H-imidazole 4-methylimidazole 4-methylpyrazole 2,5-dihydro-1H-pyrrole isopropyl isocyanide 1-methyl-5-aminopyrazole 1-methyl-3-aminopyrazole 1,1'-biaziridine N-methylazetidine 2-methyl-1,5-diazabicyclo[3.1.0]hexane pyrrole-2-carbonitrile 1-methylcyclopropene-3-carbonitrile 1-methylcyclopropanecarbonitrile a based on revised geometry presented herein. S10-280.192105-280.167289-226.048360-171.907008-171.895868-227.263020-227.228274-227.245979-227.247469-173.106692-173.099428-392.029807-228.424012-208.687789-264.171579-319.481203-319.479691-319.455624-319.531961-265.373642-265.385488-265.364443-211.206058-211.241107-320.689034-320.692408-266.449752-212.382564-305.772623-302.270916-248.048523-249.298958-280.186959-280.162065-226.042740-171.902340-171.890823-227.255951-227.221448-227.240441-227.242178-173.101691-173.094002-392.020939-228.417315-208.681053-264.164372-319.474318-319.472769-319.448590-319.525431-265.367261-265.379058-265.357948-211.200403-211.234132-320.681216-320.684591-266.442968-212.376216-305.764932-302.264369-248.041368-249.291766

Table S2. Gas phase total energies at 0 K and enthalpies at 298.15 K for compounds from ref. [1] at the W1BD level of theory. compound chlorotrifluoromethane cyanogen chloride phosgene carbonic difluoride tetrafluoromethane trichloromethane trifluoromethane hydrogen cyanide dichloromethane difluoromethane formaldehyde formic acid chloromethane methane methanol methanethiol methylamine carbon monoxide carbon dioxide carbon disulfide acetylene 1,1-dichloroethene cis-1,2-dichloroethene trans-1,2-dichloroethene 1,1-difluoroethene chloroethene fluoroethene acetonitrile ethylene acetaldehyde ethylene oxide acetic acid ethane ethanol dimethyl sulfoxide dimethylamine propyne cyclopropene propene cyclopropane acetone oxetane propylene oxide trimethylamine furan pyrrole cyclopropanecarbonitrile cyclobutene methylenecyclopropane 1-methylcyclopropene bicyclo[1.1.0]butane cis-2-butene trans-2-butene S11 E0-799.398776-554.343470-1036.373472-313.243369-437.845399-1423.184182-338.495212-93.446576-962.283360-239.141787-114.534541-189.841676-501.380555-40.479078-115.732362-439.629836-95.829469-113.372554-188.684961-836.420670-77.325127-1000.370459-1000.371779-1000.371059-277.227678-539.464749-177.888606-132.754347-78.554617-153.842538-153.798850-229.148599-79.769173-155.031769-554.169737-135.113938-116.628248-116.590555-117.853582-117.840025-193.148996-193.095726-193.101331-174.403419-230.040207-210.152035-210.121580-155.923441-155.911373-155.893933-155.899188-157.150403-157.152190 H298-799.393451-554.339285-1036.368544-313.239113-437.840490-1423.178707-338.490777-93.443083-962.278806-239.137702-114.530727-189.837549-501.376575-40.475262-115.728060-439.625259-95.825074-113.369249-188.681389-836.416619-77.321361-1000.365198-1000.366529-1000.365553-277.222989-539.460248-177.884296-132.749769-78.550623-153.837683-153.794731-229.143043-79.764719-155.026457-554.163102-135.108529-116.623331-116.586258-117.848524-117.835682-193.142544-193.090599-193.095932-174.396941-230.035520-210.147082-210.115814-155.918635-155.906116-155.888177-155.894456-157.143880-157.145727

2-methyl-1-propene S12-157.154238-157.147924

Table S3. Gas phase (298.15 K, 101.325 kpa) enthalpies of formation ( fh (g)) for all compounds from ref. [1] estimated at the G4 level of theory using the respective atomization energy approaches in ref. [2, 3] and ref. [4-6]. compound chlorotrifluoromethane cyanogen chloride difluorodichloromethane phosgene fluorotrichloromethane tetrachloromethane carbonic difluoride tetrafluoromethane trichloromethane trifluoromethane hydrogen cyanide dichloromethane difluoromethane formaldehyde formic acid chloromethane methane methanol methanethiol methylamine carbon monoxide carbon dioxide carbon disulfide chlorotrifluoroethene tetrachloroethene trifluoroacetonitrile tetrafluoroethene trichloroethene trifluoroethene acetylene 1,1-dichloroethene cis-1,2-dichloroethene trans-1,2-dichloroethene 1,1-difluoroethene chloroethene 1,1,1-trichloroethane fluoroethene 1,1,1-trifluoroethane acetonitrile ethylene acetaldehyde ethylene oxide acetic acid ethane ethanol dimethyl sulfoxide dimethylamine propyne cyclopropene propene cyclopropane acetone S13 fh (g) [2, -707.6 129.3-492.2-220.7-288.3-98.0-606.0-931.7-100.4-695.2 128.5-92.5-450.3-111.2-377.6-81.1-74.4-200.3-21.6-19.3-113.7-396.0 105.8-505.6-24.6-498.5-670.2-14.1-495.4 229.1 2.8 0.6 3.2-348.1 22.8-146.1-140.7-750.3 73.3 52.6-165.3-53.1-428.8-82.9-233.1-146.7-15.3 186.2 285.1 21.1 55.2-214.9 3] fh (g) [4-6] -708.9 128.9-493.3-221.8-289.2-98.7-607.5-933.2-101.0-696.4 128.1-93.0-451.3-112.1-379.0-81.5-74.8-201.2-22.6-19.7-114.5-397.4 104.2-507.3-25.6-500.1-672.1-15.0-496.96 228.4 1.9-0.3 2.3-349.3 22.0-147.1-141.7-751.9 72.6 51.9-166.5-54.3-430.5-83.6-234.3-148.5-16.0 185.2 284.1 20.1 54.2-216.4

oxetane propylene oxide trimethylamine pyrazine pyrimidine pyridazine furan diketene thiophene pyrrole cyclopropanecarbonitrile cyclobutene methylenecyclopropane 1-methylcyclopropene bicyclo[1.1.0]butane cis-2-butene trans-2-butene 2-methyl-1-propene tetrahydrofuran butane isobutane pyridine bicyclo[1.1.0]butane-1-carbonitrile 1,3-cyclopentadiene 2-methyl-1-buten-3-yne cyclopropylacetylene bicyclo[2.1.0]pent-2-ene spiropentane bicyclo[2.1.0]pentane 1,1-dimethylcyclopropane pentane isopentane neopentane benzene fulvene 3,4-dimethylenecyclobut-1-ene tris(methylene)cyclopropane phenol aniline 2-methylpyridine bicyclo[2.1.0]pentane-1-carbonitrile hexane 2,2-dimethylbutane 2,3-dimethylbutane toluene 2,5-norbornadiene quadricyclane spiro[2,4]hepta-4,6-diene anti-tricyclo[3.2.0.02,4]hept-6-ene tetracyclo[4.1.0.02,4.03,5]heptane 1,2-bis(methylene)cyclobutane 3-methylenecyclopentene bicyclo[2.1.1]hex-2-ene bicyclo[2.2.0]hex-1(4)-ene benzyne phenylacetylene bicyclo[4.2.0]octa-1,3,5-triene S14-78.7-93.8-24.4 205.3 186.8 279.8-32.6-190.4 112.7 109.7 186.3 163.9 193.8 241.5 224.6-3.6-9.0-15.3-178.9-123.6-132.0 140.8 352.1 137.1 254.8 297.1 329.6 185.2 157.8-8.8-144.3-150.6-166.6 85.6 216.6 339.7 441.3-89.4 89.7 99.5 278.4-165.2-182.3-174.4 52.6 239.7 334.5 227.5 374.2 368.1 211.4 113.5 230.3 383.1 459.6 320.1 200.9-80.3-95.4-25.5 203.9 185.4 278.4-34.5-192.9 110.7 108.3 184.9 162.6 192.4 240.1 223.2-5.0-10.4-16.7-180.9-125.0-133.4 139.1 350.4 135.4 253.1 295.4 327.9 183.5 156.1-10.6-146.1-152.4-168.3 83.6 214.6 337.7 439.2-92.0 87.6 97.4 276.4-167.3-184.4-176.5 50.2 237.3 332.1 225.1 371.8 365.7 209.3 111.4 228.2 381.1 457.5 317.4 198.2

3,6-bis(methylene)-1,4-cyclohexadiene 1-cyclopropylpenta-1,3-diyne cyclopropylbenzenea trans-bicyclo[6.1.0]nona-2,4,6-triene cis-bicyclo[4.3.0]nona-3,7-diene octahydrodicyclopropa[cd,gh]pentalene (1α,2α,4α,5α)-tricyclo[3.2.1.02,4]oct-6-ene bicyclo[3.2.1]octa-2,6-diene 2,3-bis(methylene)bicyclo[2.2.0]hexane 7-methylenebicyclo[2.2.1]heptane anti-tricyclo[4.2.0.02,5]octane 1-propynylbenzene hexafluorobenzene 1,2,3-trichlorobenzene 1,2,4-trichlorobenzene 1,3,5-trichlorobenzene o-dichlorobenzene m-dichlorobenzene p-dichlorobenzene o-difluorobenzene m-difluorobenzene p-difluorobenzene chlorobenzene 1-buten-3-yne bicyclo[1.1.0]but-1(3)-ene (Z)-3-penten-1-yne (Z)-hexa-1,5-diyne-3-ene (E)-hexa-1,5-diyne-3-ene 1,2-bis(methylene)cyclobutane trans-2,3,4-hexatriene cis-2,3,4-hexatriene bicyclo[2.2.0]hexane 1,1-diethynylcyclopropane bicyclo[3.2.0]hepta-2,6-diene 3-methylene-1,4-cyclohexadiene 6-methylfulvene 2-norbornene nortricyclene tricyclo[4.1.0.02,4]heptane dispiro[2.0.2.1]heptane 5,5-dimethyl-1,3-cyclopentadiene tricyclo[4.1.0.02,7]heptane spiro[cyclopropane(1,5')bicyclo[2.1.0]pentane anti-tricyclo[4.1.0.02,4]heptane anti-tricyclo[3.2.0.02,4]heptane 3-(cis-ethylidene)-1-cyclopentene bicyclo[3.2.0]hept-1(5)-ene bicyclo[3.2.0]hept-1-ene styrene 5-(1-methylethylidene)-1,3-cyclopentadiene 2,3-dihydrothiophene 2,5-dihydrothiophene 1,3-dioxol-2-one cyclopropanone 1,3,5-trioxane carbon suboxide 4-methylene-2-oxetanone S15 222.7 481.6 157.0 344.7 113.1 175.8 233.7 148.3 307.6 49.1 217.4 279.5-949.3 5.5-0.1-5.8 28.0 22.0 22.7-287.1-302.9-299.6 52.4 290.3 567.8 255.0 527.3 526.6 211.4 261.0 261.0 131.7 547.1 263.1 169.4 182.1 82.0 71.5 155.9 312.5 81.6 196.4 282.8 155.9 238.7 86.9 184.3 171.9 150.3 145.5 82.2 84.5-396.2 20.4-468.3-89.9-190.4 219.9 478.9 153.9 341.7 110.0 173.1 231.0 145.6 304.9 46.3 214.6 276.4-953.0 3.2-2.3-8.0 25.8 19.7 20.5-289.7-305.5-302.2 50.3 288.9 566.4 253.3 525.2 524.6 209.3 258.9 259.0 129.6 544.7 260.7 167.0 179.7 79.6 69.1 153.5 310.1 79.2 194.0 280.4 153.5 236.3 84.5 181.9 169.5 147.6 142.7 80.1 82.5-398.8 18.8-470.9-91.9-192.9

norbornan-7-one 2-propenenitrile 1,3,5-triazine 1H-imidazole 1H-pyrazole propiolonitrile 2-methyl-1H-imidazole 2-butynedinitrile 2,3-diazabicyclo[2.2.1]-hept-2-ene cyclobutadiene 1,2,3-butatriene methylenecyclopropene methylcyclopropane 1,3-pentadiyne penta-1,4-diyne 1,2,3,4-pentatetraene 1-penten-3-yne [1.1.1]propellane bicyclo[1.1.1]pentane 1-methylcyclobutene 3,3-dimethylcyclopropene 1,2-dimethylcyclopropene methylmethylenecyclopropane ethylidenecyclopropane hex-3-en-1,5-diyne 1,4-hexadiyne bicyclo[2.2.0]hexa-2,5-diene benzvalene 1-methyl-1,3-cyclopentadiene 5-methyl-1,3-cyclopentadiene bicyclo[2.2.0]hex-2-ene 1,3-bis(methylene)cyclobutane 2-methyl-1-penten-3-yne cyclopropylidene cyclopropane ethynylcyclobutane tricyclo[3.1.0.02,6]hexane bicyclo[2.1.1]hexane 1,3-dimethylbicyclo[1.1.0]butane 1,1-dimethyl-2-methylenecyclopropane 3,3-dimethylcyclobutene bicyclo[4.1.0]hepta-1,3,5-triene 5-ethenylidene-1,3-cyclopentadiene trans-1,2-diethynylcyclopropane bicyclo[3.2.0]hepta-1,4,6-triene cis-1,2-diethynylcyclopropane 5-methylenebicyclo[2.2.0]hex-2-ene spiro[3.3]hepta-2,5-diene tricyclo[4.1.0.02,7]hept-3-ene tricyclo[4.1.0.01,3]heptane tricyclo[3.1.1.03,6]heptane 1-methyl-1,2-propadienylcyclopropane cyclopentyl acetylene (1α,4α,5β)-5-methyl-2-methylenebicyclo[2.1.0]pentane endo-2-methylene-5-methylbicyclo[2.1.0]pentane 5,5-dimethylbicyclo[2.1.0]pent-2-ene syn-tricyclo[3.2.0.02,4]heptane bicyclo[4.2.0]octa-1,3,5,7-tetraene S16-142.2 186.3 224.1 131.4 177.3 373.0 88.8 530.1 205.8 430.4 322.6 388.9 26.4 415.0 455.4 448.7 250.0 360.2 201.6 121.1 220.7 199.8 164.5 163.0 526.6 415.6 404.8 385.9 101.1 113.1 261.6 222.0 214.7 337.5 267.7 229.3 59.8 154.6 128.5 97.3 380.3 354.1 540.7 446.8 544.6 354.6 365.8 312.5 241.6 233.9 236.2 169.4 259.6 221.1 264.9 276.6 409.4-145.2 185.3 223.0 130.3 176.3 371.9 87.4 528.7 204.1 429.1 321.2 387.5 25.0 413.3 453.7 447.0 248.3 358.5 199.9 119.3 219.0 198.1 162.7 161.3 524.6 413.6 402.8 383.9 99.1 111.0 259.5 219.9 212.7 335.4 265.6 227.3 57.7 152.5 126.4 95.2 377.9 351.7 538.4 444.4 542.2 352.2 363.4 310.1 239.2 231.5 233.8 167.0 257.2 218.7 262.5 274.1 406.7

2,4,6-octatriyne (1α,2α,5α,6α)-tricyclo[4.2.0.02,5]octa-3,7-diene (1α,2β,5β,6α)-tricyclo[4.2.0.02,5]octa-3,7-diene bicyclo[2.2.2]octa-2,5,7-triene 2a,2b,4a,4b-tetrahydrocyclopropa[cd]pentalene pentacyclo[3.3.0.02,4.03,7.06,8]octane 7-methylenebicyclo[2.2.1]hepta-2,5-diene tricyclo[4.1.1.07,8]octa-2,4-diene cycloocta-1,5-dien-3-yne cycloocta-1,3-dien-6-yne 3-methylenetetracyclo[3.2.0.02,7.04,6]heptane 1,5-dihydropentalene 1-ethynyl-1-(1-propynyl)cyclopropane tetrakis(methylene)cyclobutane heptafulvene 5-methylenebicyclo[2.2.1]hept-2-ene 1,5-dimethyl-3-exo-methylenetricyclo[2.1.0.0]pentane tricyclo[4.1.1.07,8]oct-3-ene 1-methylnorbornadiene 2-methylnorbornadiene tricyclo[4.1.1.07,8]oct-2-ene 6-methyltricyclo[4.1.0.02,7]hept-3-ene 1-methyltricyclo[4.1.0.02,7]hept-3-ene 7-methylenebicyclo[3.2.0]hept-1-ene bicyclo[3.3.0]octa-2,6-diene 5-methyl-3H-1,2-dithiole-3-thione 4-methyl-3H-1,2-dithiole-3-thione dihydro-2(3h)-thiophenthione 2,2-dimethylthiirane 2-methylthietane 3-methylthietane 2-methyl-1,3-dithiacyclopentane 4-methyl-1,3-dithiolane 3-methyl-1,2-dithiolane 4-methyl-1,2-dithiolane trimethylthiirane 3,3-dimethylthietane 7-thiabicyclo[4.1.0]heptane 2-(1,1-dimethylethyl)thiirane thieno[3,2-b]thiophene thieno[2,3-b]thiophene thieno[3,4-b]thiophene dithio-p-benzoquinone benzodithiete methyl-oxirane cyclopropylidenemethanone 2(3H)-furanone 1,4-dioxin 3(2H)-furanone cyclobutane-1,3-dione 1,2-cyclobutanedione 2,5-dihydrofuran 2-methyl-1-propen-1-one 3-methyleneoxetane 4-methylene-1,3-dioxolane α-trimethylethylene oxide 7-oxabicyclo[2.2.1]heptane S17 597.2 502.6 475.6 296.0 303.7 445.6 344.0 407.8 401.9 436.7 429.1 234.8 507.1 387.1 266.8 187.1 421.5 307.1 202.8 199.7 305.9 273.0 275.3 265.7 131.4 151.5 149.4 65.6 2.5 26.2 29.1-4.5-2.7-12.3-8.8-28.6-9.2 130.9-43.8 206.1 214.1 225.0 306.8 242.0-93.8 108.0-248.3-81.1-205.9-180.2-166.6-60.9-86.5 22.9-222.9-173.6-176.6 594.5 499.9 472.9 293.3 300.9 442.8 341.3 405.1 399.2 434.0 426.4 232.1 504.4 384.4 264.0 184.4 418.8 304.4 200.0 196.9 303.1 270.2 272.5 263.0 128.6 148.2 146.1 62.9 0.5 24.2 27.0-7.1-5.4-15.0-11.4-31.0-11.5 128.2-46.6 202.8 210.7 221.7 303.4 238.7-95.4 106.1-250.7-83.6-208.3-182.6-169.0-62.8-88.4 21.0-225.3-175.9-179.2

2-oxaspiro[3,3]heptane 1,2,4-triazine 1,2,3-triazine 2-aziridinecarbonitrile 1-azetine cyclopropanimine dimethylcyanamide 3,3-dimethyldiazirine 1-pyrazoline 2-pyrazoline azetidine 1-methylaziridine 5-(dimethylamino)tetrazole 3,3-dimethyldiaziridine cyanoallene 1,1-dicyanoethane 3-methyl-1,2,4-triazine 6-methyl-1,2,4-triazine 4-methyl-1,2,3-triazine 4-aminopyrimidine 1-methyl-1H-imidazole 4-methylimidazole 4-methylpyrazole 2,5-dihydro-1H-pyrrole isopropyl isocyanide 1-methyl-5-aminopyrazole 1-methyl-3-aminopyrazole 1,1'-biaziridine N-methylazetidine 2-methyl-1,5-diazabicyclo[3.1.0]hexane pyrrole-2-carbonitrile 1-methylcyclopropene-3-carbonitrile 1-methylcyclopropanecarbonitrile a based on revised geometry presented herein. S18-39.5 335.2 400.5 269.5 193.7 224.0 140.7 231.3 181.5 176.9 101.4 121.6 327.5 148.1 618.7 225.2 286.9 290.9 354.4 152.7 123.6 92.6 148.0 117.3 28.8 174.7 165.9 355.9 86.8 216.7 237.8 378.9 152.5-42.1 334.1 399.5 268.4 192.7 222.9 139.7 230.3 180.4 175.8 100.3 120.5 326.4 147.1 617.4 223.8 285.5 289.5 353.0 151.3 122.2 91.2 146.6 115.9 27.4 173.3 164.4 354.5 85.4 215.0 236.0 377.2 150.8

Table S4. Gas phase (298.15 K, 101.325 kpa) enthalpies of formation ( fh (g)) for compounds from ref. [1] estimated at the W1BD level of theory using the respective atomization energy approaches in ref. [2, 3] and ref. [4-6]. compound chlorotrifluoromethane cyanogen chloride phosgene carbonic difluoride tetrafluoromethane trichloromethane trifluoromethane hydrogen cyanide dichloromethane difluoromethane formaldehyde formic acid chloromethane methane methanol methanethiol methylamine carbon monoxide carbon dioxide carbon disulfide acetylene 1,1-dichloroethene cis-1,2-dichloroethene trans-1,2-dichloroethene 1,1-difluoroethene chloroethene fluoroethene acetonitrile ethylene acetaldehyde ethylene oxide acetic acid ethane ethanol dimethyl sulfoxide dimethylamine propyne cyclopropene propene cyclopropane acetone oxetane propylene oxide trimethylamine furan pyrrole cyclopropanecarbonitrile cyclobutene methylenecyclopropane 1-methylcyclopropene bicyclo[1.1.0]butane cis-2-butene S19 fh (g) [2, -720.9 132.7-226.6-612.3-944.5-110.6-705.4 131.2-102.5-457.5-110.5-381.0-88.3-76.4-205.1-28.2-24.6-110.1-394.6 114.4 228.3-5.1-8.6-6.0-357.2 16.3-147.0 73.8 50.0-168.6-55.9-435.3-88.6-240.7-157.4-21.0 183.3 280.6 15.6 49.3-221.2-84.9-98.9-30.4-39.6 102.6 184.7 155.8 188.6 235.7 219.3-12.0 3] fh (g) [4-6] -722.2 132.3-227.6-613.7-946.1-111.2-706.7 130.8-103.0-458.5-111.4-382.4-88.7-76.8-205.9-29.2-25.0-111.0-396.0 112.8 227.6-6.0-9.5-6.9-358.5 15.5-148.0 73.1 49.3-169.9-57.1-437.0-89.3-241.9-159.3-21.8 182.3 279.6 14.6 48.3-222.8-86.4-100.4-31.5-41.5 101.3 183.4 154.4 187.3 234.4 217.9-13.4

trans-2-butene 2-methyl-1-propene S20-16.9-22.7-18.3-24.0

G09 archive entries at the CBS-Q//B3 level of theory for methane, ethyne, ethene, ethane, propyne, propene, and benzene methane Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.044132 E(Thermal)= 0.047003 E(SCF)= -40.212152 DE(MP2)= -0.192065 DE(CBS)= -0.019397 DE(MP34)= -0.022193 DE(CCSD)= -0.003629 DE(Int)= 0.007329 DE(Empirical)= -0.012035 CBS-QB3 (0 K)= -40.410009 CBS-QB3 Energy= -40.407138 CBS-QB3 Enthalpy= -40.406194 CBS-QB3 Free Energy= -40.429673 0,1\C,0,-1.1427914343,0.261705665,-0.004288340 5\H,0,-0.0521121111,0.2617331756,0.0039123063\H,0,-1.5068436429,1.2898 335659,0.0039140305\H,0,-1.5137600693,-0.2632063591,0.8768880142\H,0,1.4991327424,-0.2425060473,-0.9037960105\\Version=EM64L-G09RevA.02\Sta te=1-a\hf/cbsb3=-40.2121516\e2(cbs)/cbsb3=-0.2114613\cbs-int/cbsb3=0.0 073295\OIii/CbsB3=2.0786409\MP2/CbsB4=-40.3674683\MP4(SDQ)/CbsB4=-40.3 896612\MP4(SDQ)/6-31+G(d')=-40.3561342\QCISD(T)/6-31+G(d')=-40.3597631 \CBSQB3=-40.4100085\FreqCoord=-2.1595628378,0.4945520343,-0.0081037891,-0.0984776182,0.4946040217,0.0073931875,-2.8475218102,2.4374321965,0. 0073964457,-2.8605919618,-0.4973879352,1.6570781961,-2.8329503201,-0.4 58270015,-1.7079269399\PG=C01 [X(C1H4)]\NImag=0\\ ethyne Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.026714 E(Thermal)= 0.029536 E(SCF)= -76.848478 DE(MP2)= -0.305771 DE(CBS)= -0.028886 DE(MP34)= -0.015555 DE(CCSD)= -0.012038 DE(Int)= 0.010951 DE(Empirical)= -0.014368 CBS-QB3 (0 K)= -77.187430 CBS-QB3 Energy= -77.184609 CBS-QB3 Enthalpy= -77.183665 CBS-QB3 Free Energy= -77.207044 1\1\GINC-CL1N048\Mixed\CBS-QB3\CBS-QB3\C2H2\KFOREST\27-Dec-2010\0\\# C BS-QB3\\<< job name >>\\0,1\C,0,-1.1514339031,0.1710312935,-0.27822632 52\C,0,-0.0606816401,-0.104000256,0.1343033404\H,0,-2.1190389328,0.415 0114527,-0.6441808989\H,0,0.9069234603,-0.347980433,0.5002579409\\Vers ion=em64l-g09reva.02\state=1-sg\hf/cbsb3=-76.8484776\e2(cbs)/cbsb3=-0. 3346578\CBS-Int/CbsB3=0.0109514\OIii/CbsB3=2.4814645\MP2/CbsB4=-77.086 5517\MP4(SDQ)/CbsB4=-77.1021068\MP4(SDQ)/6-31+G(d')=-77.0874429\QCISD( T)/6-31+G(d')=-77.0994804\CBSQB3=-77.1874302\FreqCoord=-2.175894737,0. 323202305,-0.5257715576,-0.1146716811,-0.1965320017,0.2537965322,-4.00 44032479,0.7842579876,-1.2173254789,1.7138369635,-0.657587718,0.945350 504\PG=C*V [C*(H1C1C1H1)]\NImag=0\\ ethene Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.050304 E(Thermal)= 0.053355 E(SCF)= -78.062195 DE(MP2)= -0.328700 DE(CBS)= -0.031914 DE(MP34)= -0.027882 DE(CCSD)= -0.010530 DE(Int)= 0.011839 DE(Empirical)= -0.017557 CBS-QB3 (0 K)= -78.416635 CBS-QB3 Energy= -78.413585 CBS-QB3 Enthalpy= -78.412641 CBS-QB3 Free Energy= -78.438814 1\1\GINC-CL1N119\Mixed\CBS-QB3\CBS-QB3\C2H4\KFOREST\27-Dec-2010\0\\# C BS-QB3\\<< job name >>\\0,1\C,0,-0.9845641425,0.1269298546,-0.21898717 74\C,0,0.2339353313,-0.1699329049,0.2141575404\H,0,-1.3145675235,1.153 S21

7947064,-0.3362902937\H,0,-1.7035073571,-0.6443811079,-0.4745536259\H, 0,0.9528767948,0.6013779025,0.4697283815\H,0,0.5639372566,-1.196797791 1,0.3314646156\\Version=EM64L-G09RevA.02\State=1-A\HF/CbsB3=-78.062194 7\E2(CBS)/CbsB3=-0.3606138\CBS-Int/CbsB3=0.0118387\OIii/CbsB3=3.032347 9\MP2/CbsB4=-78.3239418\MP4(SDQ)/CbsB4=-78.3518238\MP4(SDQ)/6-31+G(d') =-78.3187008\QCISD(T)/6-31+G(d')=-78.329231\CBSQB3=-78.4166351\FreqCoo rd=-1.8605565897,0.2398626633,-0.4138257919,0.4420737112,-0.3211266413,0.4046991014,-2.4841726025,2.1803560087,-0.6354965563,-3.2191623703,1.2177038191,-0.8967763883,1.8006761805,1.1364395381,0.8876579979,1.06 56869711,-2.2616200617,0.6263773462\PG=C01 [X(C2H4)]\NImag=0\\ ethane Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.073633 E(Thermal)= 0.077138 E(SCF)= -79.257252 DE(MP2)= -0.360337 DE(CBS)= -0.035502 DE(MP34)= -0.035149 DE(CCSD)= -0.008155 DE(Int)= 0.013093 DE(Empirical)= -0.020903 CBS-QB3 (0 K)= -79.630573 CBS-QB3 Energy= -79.627068 CBS-QB3 Enthalpy= -79.626124 CBS-QB3 Free Energy= -79.653704 1\1\GINC-CL1N119\Mixed\CBS-QB3\CBS-QB3\C2H6\KFOREST\27-Dec-2010\0\\# C BS-QB3\\<< job name >>\\0,1\C,0,-0.8666458831,0.0921802571,-0.18395326 01\C,0,0.5278105891,-0.2748202541,0.3318532638\H,0,-1.0020783531,1.176 2379129,-0.2264990859\H,0,-1.6491242164,-0.3129457095,0.4633000364\H,0,-1.0343998972,-0.3010842316,-1.190209565\H,0,0.6955654555,0.118444632 9,1.3381093161\H,0,1.3102892016,0.1303052953,-0.3154000569\H,0,0.66324 31036,-1.3588779029,0.3743993516\\Version=EM64L-G09RevA.02\State=1-A\H F/CbsB3=-79.2572525\E2(CBS)/CbsB3=-0.3958386\CBS-Int/CbsB3=0.0130926\O Iii/CbsB3=3.6101479\MP2/CbsB4=-79.5480209\MP4(SDQ)/CbsB4=-79.5831702\M P4(SDQ)/6-31+G(d')=-79.5327308\QCISD(T)/6-31+G(d')=-79.5408862\CBSQB3= -79.6305733\FreqCoord=-1.6377233733,0.1741954407,-0.3476212828,0.99741 74635,-0.5193350161,0.6271117849,-1.893653651,2.2227675225,-0.42802124 17,-3.1163931282,-0.5913816854,0.8755101862,-1.9547325175,-0.568966740 6,-2.2491701185,1.3144282184,0.2238279181,2.5286601434,2.476087746,0.2 462413217,-0.5960197299,1.2533478253,-2.5679070845,0.7075122388\PG=C01 [X(C2H6)]\NImag=0\\ propyne Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.054921 E(Thermal)= 0.058896 E(SCF)= -115.906126 DE(MP2)= -0.474799 DE(CBS)= -0.045243 DE(MP34)= -0.027644 DE(CCSD)= -0.016344 DE(Int)= 0.016745 DE(Empirical)= -0.023242 CBS-QB3 (0 K)= -116.421732 CBS-QB3 Energy= -116.417757 CBS-QB3 Enthalpy= -116.416813 CBS-QB3 Free Energy= -116.445951 1\1\GINC-CL1N119\Mixed\CBS-QB3\CBS-QB3\C3H4\KFOREST\27-Dec-2010\0\\# C BS-QB3\\<< job name >>\\0,1\C,0,-1.0159876863,0.079940635,-0.157129556 4\C,0,0.2948075034,-0.3086866506,0.3473465132\H,0,0.3945563836,-0.0637 954259,1.4084930893\H,0,1.0919763417,0.2088472221,-0.193597866\H,0,0.4 549433314,-1.38453731,0.2339884677\C,0,-2.0962493904,0.4001924697,-0.5 72622942\H,0,-3.0515364835,0.6834390596,-0.9402377057\\Version=EM64L-G 09RevA.02\State=1-A\HF/CbsB3=-115.9061257\E2(CBS)/CbsB3=-0.5200423\CBS -Int/CbsB3=0.0167451\OIii/CbsB3=4.014239\MP2/CbsB4=-116.2798306\MP4(SD Q)/CbsB4=-116.3074743\MP4(SDQ)/6-31+G(d')=-116.2759816\QCISD(T)/6-31+G (d')=-116.2923259\cbsqb3=-116.4217322\freqcoord=-1.9199384814,0.151065 9071,-0.296931829,0.5571054433,-0.5833332305,0.6563897832,0.745603509, S22

-0.1205558834,2.6616661988,2.0635362295,0.3946640534,-0.3658469466,0.8 597183023,-2.6163963367,0.4421741221,-3.961337254,0.7562541683,-1.0821 005378,-5.7665682383,1.2915126511,-1.7767917636\PG=C01 [X(C3H4)]\NImag =0\\ propene Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.078518 E(Thermal)= 0.082630 E(SCF)= -117.113448 DE(MP2)= -0.499448 DE(CBS)= -0.048165 DE(MP34)= -0.039656 DE(CCSD)= -0.015252 DE(Int)= 0.017624 DE(Empirical)= -0.026405 CBS-QB3 (0 K)= -117.646232 CBS-QB3 Energy= -117.642121 CBS-QB3 Enthalpy= -117.641177 CBS-QB3 Free Energy= -117.671256 1\1\GINC-CL1N048\Mixed\CBS-QB3\CBS-QB3\C3H6\KFOREST\27-Dec-2010\0\\# C BS-QB3\\<< job name >>\\0,1\C,0,0.6766967591,0.9904807556,0.8644228359 \C,0,1.7717488125,1.9657164304,1.182073534\C,0,3.0714276771,1.68629527 52,1.1866004129\H,0,-0.0175556239,0.8899252675,1.7061426477\H,0,0.0829 781647,1.3300273721,0.0083875778\H,0,1.0764099905,0.0006849103,0.63151 1368\H,0,1.4520858329,2.9777936031,1.4255022751\H,0,3.8145451745,2.438 6114952,1.4256245192\H,0,3.4401633468,0.6921754781,0.9507325632\\Versi on=em64l-g09reva.02\state=1-a\hf/cbsb3=-117.1134482\e2(cbs)/cbsb3=-0.5 476134\CBS-Int/CbsB3=0.0176236\OIii/CbsB3=4.5603661\MP2/CbsB4=-117.512 5534\MP4(SDQ)/CbsB4=-117.5522097\MP4(SDQ)/6-31+G(d')=-117.5026096\QCIS D(T)/6-31+G(d')=-117.5178617\CBSQB3=-117.6462325\FreqCoord=1.278771549 7,1.8717373681,1.6335224227,3.3481200319,3.7146657083,2.2337952482,5.8 041571469,3.1866362499,2.2423498071,-0.0331753213,1.6817150344,3.22414 23478,0.1568060062,2.5133874825,0.0158502249,2.0341200887,0.0012942928,1.1933835352,2.7440445456,5.6272143899,2.6938089024,7.2084457013,4.60 83078705,2.6940399097,6.5009665779,1.3080220895,1.7966241701\PG=C01 [X (C3H6)]\NImag=0\\ benzene Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.099185 E(Thermal)= 0.103619 E(SCF)= -230.773869 DE(MP2)= -0.939373 DE(CBS)= -0.090273 DE(MP34)= -0.035529 DE(CCSD)= -0.038115 DE(Int)= 0.031373 DE(Empirical)= -0.043126 CBS-QB3 (0 K)= -231.789728 CBS-QB3 Energy= -231.785295 CBS-QB3 Enthalpy= -231.784351 CBS-QB3 Free Energy= -231.817204 1\1\GINC-CL1N102\Mixed\CBS-QB3\CBS-QB3\C6H6\KFOREST\27-Dec-2010\0\\# C BS-QB3\\<< job name >>\\0,1\C,0,-3.6386452727,0.8501326996,-1.29035279 39\C,0,-4.1210486895,-0.3353312377,-0.7391506175\C,0,-3.254022064,-1.1 944245495,-0.0667920014\C,0,-1.9047347273,-0.8680726996,0.0543827939\C,0,-1.4223313105,0.3173912377,-0.4968193825\C,0,-2.289357936,1.1764845 495,-1.1691779986\H,0,-4.3133439927,1.5186025871,-1.8134439599\H,0,-5. 1709394581,-0.5892976248,-0.8334882141\H,0,-3.6292476223,-2.1170127146,0.3618905019\H,0,-1.2300360073,-1.5365425871,0.5774739599\H,0,-0.3724 405419,0.5713576248,-0.4024817859\H,0,-1.9141323777,2.0990727146,-1.59 78605019\\Version=EM64L-G09RevA.02\State=1-AG\HF/CbsB3=-230.7738693\E2 (CBS)/CbsB3=-1.0296464\CBS-Int/CbsB3=0.031373\OIii/CbsB3=7.4484387\MP2 /CbsB4=-231.5216532\MP4(SDQ)/CbsB4=-231.5571825\MP4(SDQ)/6-31+G(d')=-2 31.5089651\QCISD(T)/6-31+G(d')=-231.5470806\CBSQB3=-231.7897285\FreqCo ord=-6.8760430601,1.6065179789,-2.4384133952,-7.7876534034,-0.63368420 31,-1.396792238,-6.1492105314,-2.2571352849,-0.1262185906,-3.599426990 4,-1.6404196657,0.1027685867,-2.6878166471,0.5997825163,-0.9388525704, S23

-4.3262595192,2.2232335981,-2.2094262179,-8.1510388632,2.8697429943,-3.4269124416,-9.7716594256,-1.1136111216,-1.5750644596,-6.8582840746,-4.0005742505,0.6838739387,-2.3244311873,-2.9036446811,1.0912676332,-0.7 038106249,1.0797094348,-0.7605803489,-3.6171859759,3.9666725636,-3.019 5187471\PG=CI [X(C6H6)]\NImag=0\\ S24

Revised G09 archive entry and visualized geometry at the Gaussian-4 (G4) level of theory for cyclopropylbenzene Temperature= 298.150000 Pressure= 1.000000 E(ZPE)= 0.160044 E(Thermal)= 0.167596 E(CCSD(T))= -347.864018 E(Empiric)= -0.159781 DE(Plus)= -0.020921 DE(2DF)= -0.284450 E(Delta-G3XP)= -0.510047 DE(HF)= -0.033422 G4(0 K)= -348.712594 G4 Energy= -348.705042 G4 Enthalpy= -348.704098 G4 Free Energy= -348.744912 1\1\GINC-CL1N142\Mixed\G4\G4\C9H10\KFOREST\30-Dec-2010\0\\# G4\\<< job name >>\\0,1\C,0,-0.7009892089,0.890707462,0.308811964\C,0,-0.7563718 364,-0.4987048824,0.4658953455\C,0,-1.8237862281,1.5358333103,-0.22655 89827\C,0,-1.8894874459,-1.221432319,0.1026654321\C,0,-2.9572268469,0. 8166377119,-0.5903527566\C,0,-2.9971190593,-0.5668111381,-0.4279894662 \H,0,0.1031328391,-1.0186102848,0.8792520075\H,0,-1.8167638683,2.61305 14123,-0.3625596414\H,0,-1.9045619087,-2.2985239159,0.2355994875\H,0,3.8140441113,1.3398600626,-1.0029292064\H,0,-3.881758811,-1.1266151828,-0.7121076239\C,0,0.5298322134,1.6250834677,0.7099697547\C,0,1.025902 472,2.8332686505,-0.0618129561\C,0,0.4688942583,3.0129844248,1.3192103 767\H,0,1.306557427,0.979139315,1.1074696855\H,0,0.4271350371,3.162099 6671,-0.9043743896\H,0,2.0955155026,2.9355373971,-0.2084291748\H,0,-0. 5112055636,3.465747024,1.4238618418\H,0,1.1528151388,3.2393078177,2.12 98483025\\Version=EM64L-G09RevA.02\State=1-A\MP2/GTBas1=-347.7535394\M P4/GTBas1=-347.8657864\CCSD(T)/G3Bas1=-347.8640179\MP2/GTBas2=-347.774 1105\MP4/GTBas2=-347.886707\MP2/GTBas3=-348.02485\MP4/GTBas3=-348.1502 366\HF/GTLargeXP=-346.7127745\MP2/GTLargeXP=-348.5554678\HF/GFHFB1=-34 6.7398546\HF/GFHFB2=-346.7449537\G4=-348.7125945\FreqCoord=-1.32467762 7,1.6831931677,0.5835700386,-1.4293356253,-0.942415649,0.8804146096,-3.446456496,2.9023043423,-0.4281344303,-3.5706138042,-2.3081725728,0.19 40095499,-5.5883488534,1.5432216254,-1.1156050318,-5.6637342097,-1.071 11782,-0.8087828789,0.1948928213,-1.9248944745,1.6615454959,-3.4331861 592,4.9379515404,-0.6851384291,-3.5991004106,-4.343580711,0.4452185084,-7.2074988291,2.5319685747,-1.8952615308,-7.3354610667,-2.1289941526, -1.3456883863,1.0012377797,3.0709626971,1.3416483991,1.9386747112,5.35 41018104,-0.1168095585,0.8860817334,5.6937154055,2.4929463237,2.469035 7139,1.8503051512,2.0928144061,0.807168242,5.9755023758,-1.709019918,3.9599504071,5.5473617333,-0.3938740585,-0.9660385127,6.5493127213,2.69 07089322,2.1785048941,6.1214046355,4.0248299963\PG=C01 [X(C9H10)]\NIma g=0\\ S25

Visualization of optimized Gaussian-4 (G4) geometries for all compounds as published in ref. [1]: Note: Geometries visualized using Gabedit v.2.2.12 [7] (bond orders assigned automatically by the software while reading the G09 output files, and may not be accurate representations of actual bond orders). chlorotrifluoromethane cyanogen chloride difluorodichloromethane phosgene fluorotrichloromethane tetrachloromethane S26

carbonic difluoride tetrafluoromethane trichloromethane trifluoromethane hydrogen cyanide dichloromethane difluoromethane S27

formaldehyde formic acid chloromethane methane methanol methanethiol methylamine S28

carbon monoxide carbon dioxide carbon disulfide chlorotrifluoroethene tetrachloroethene trifluoroacetonitrile tetrafluoroethene S29

trichloroethene trifluoroethene acetylene 1,1-dichloroethene cis-1,2-dichloroethene trans-1,2-dichloroethene 1,1-difluoroethene S30

chloroethene 1,1,1-trichloroethane fluoroethene 1,1,1-trifluoroethane acetonitrile ethylene acetaldehyde S31

ethylene oxide acetic acid ethane ethanol dimethyl sulfoxide dimethylamine propyne S32

cyclopropene propene cyclopropane acetone oxetane propylene oxide trimethylamine S33

pyrazine pyrimidine pyridazine furan diketene thiophene pyrrole S34

cyclopropanecarbonitrile cyclobutene methylenecyclopropane 1-methylcyclopropene bicyclo[1.1.0]butane cis-2-butene trans-2-butene S35

2-methyl-1-propene tetrahydrofuran butane isobutane pyridine bicyclo[1.1.0]butane-1-carbonitrile 1,3-cyclopentadiene S36

2-methyl-1-buten-3-yne cyclopropylacetylene bicyclo[2.1.0]pent-2-ene spiropentane bicyclo[2.1.0]pentane 1,1-dimethylcyclopropane pentane S37

isopentane neopentane benzene fulvene 3,4-dimethylenecyclobut-1-ene tris(methylene)cyclopropane phenol S38

aniline 2-methylpyridine bicyclo[2.1.0]pentane-1-carbonitrile hexane 2,2-dimethylbutane 2,3-dimethylbutane toluene S39

2,5-norbornadiene quadricyclane spiro[2,4]hepta-4,6-diene anti-tricyclo[3.2.0.02,4]hept-6-ene tetracyclo[4.1.0.02,4.03,5]heptane 1,2-bis(methylene)cyclobutane 3-methylenecyclopentene S40

bicyclo[2.1.1]hex-2-ene bicyclo[2.2.0]hex-1(4)-ene benzyne phenylacetylene bicyclo[4.2.0]octa-1,3,5-triene 3,6-bis(methylene)-1,4-cyclohexadiene 1-cyclopropylpenta-1,3-diyne S41

cyclopropylbenzene trans-bicyclo[6.1.0]nona-2,4,6-triene cis-bicyclo[4.3.0]nona-3,7-diene octahydrodicyclopropa[cd,gh]pentalene (1α,2α,4α,5α)-tricyclo[3.2.1.02,4]oct-6-ene bicyclo[3.2.1]octa-2,6-diene 2,3-bis(methylene)bicyclo[2.2.0]hexane S42

7-methylenebicyclo[2.2.1]-heptane anti-tricyclo[4.2.0.02,5]octane 1-propynylbenzene hexafluorobenzene 1,2,3-trichlorobenzene 1,2,4-trichlorobenzene 1,3,5-trichlorobenzene S43

o-dichlorobenzene m-dichlorobenzene p-dichlorobenzene o-difluorobenzene m-difluorobenzene p-difluorobenzene chlorobenzene S44

1-buten-3-yne bicyclo[1.1.0]but-1(3)-ene (Z)-3-penten-1-yne (Z)-hexa-1,5-diyne-3-ene (E)-hexa-1,5-diyne-3-ene 1,2-bis(methylene)cyclobutane S45

trans-2,3,4-hexatriene cis-2,3,4-hexatriene bicyclo[2.2.0]hexane 1,1-diethynylcyclopropane bicyclo[3.2.0]hepta-2,6-diene 3-methylene-1,4-cyclohexadiene S46

6-methylfulvene 2-norbornene nortricyclene tricyclo[4.1.0.02,4]-heptane dispiro[2.0.2.1]heptane 5,5-dimethyl-1,3-cyclopentadiene tricyclo[4.1.0.02,7]heptane S47

spiro[cyclopropane(1,5')bicyclo[2.1.0]pentane] anti-tricyclo[4.1.0.02,4]heptane anti-tricyclo[3.2.0.02,4]heptane 3-(cis-ethylidene)-1-cyclopentene bicyclo[3.2.0]hept-1(5)-ene bicyclo[3.2.0]hept-1-ene styrene S48

5-(1-methylethylidene)-1,3-cyclopentadiene 2,3-dihydrothiophene 2,5-dihydrothiophene 1,3-dioxol-2-one cyclopropanone 1,3,5-trioxane carbon suboxide S49

4-methylene-2-oxetanone norbornan-7-one 2-propenenitrile 1,3,5-triazine 1H-imidazole 1H-pyrazole propiolonitrile S50

2-methyl-1H-imidazole 2-butynedinitrile 2,3-diazabicyclo[2.2.1]-hept-2-ene cyclobutadiene 1,2,3-butatriene methylenecyclopropene methylcyclopropane S51

1,3-pentadiyne penta-1,4-diyne 1,2,3,4-pentatetraene 1-penten-3-yne [1.1.1]propellane bicyclo[1.1.1]pentane 1-methylcyclobutene S52

3,3-dimethylcyclopropene 1,2-dimethylcyclopropene methylmethylenecyclopropane ethylidenecyclopropane hex-3-en-1,5-diyne 1,4-hexadiyne S53

bicyclo[2.2.0]hexa-2,5-diene benzvalene 1-methyl-1,3-cyclopentadiene 5-methyl-1,3-cyclopentadiene bicyclo[2.2.0]hex-2-ene 1,3-bis(methylene)cyclobutane 2-methyl-1-penten-3-yne S54

cyclopropylidene cyclopropane ethynylcyclobutane tricyclo[3.1.0.02,6]hexane bicyclo[2.1.1]hexane 1,3-dimethylbicyclo[1.1.0]butane 1,1-dimethyl-2-methylenecyclopropane 3,3-dimethylcyclobutene S55

bicyclo[4.1.0]hepta-1,3,5-triene 5-ethenylidene-1,3-cyclopentadiene trans-1,2-diethynylcyclopropane bicyclo[3.2.0]hepta-1,4,6-triene cis-1,2-diethynylcyclopropane bicyclo[2.2.0]hex-2-ene,5-methylene spiro[3.3]hepta-2,5-diene S56

tricyclo[4.1.0.02,7]hept-3-ene tricyclo[4.1.0.01,3]heptane tricyclo[3.1.1.03,6]heptane (1-methyl-1,2-propadienyl)cyclopropane cyclopentyl acetylene (1α, 4α, 5β)-5-methyl-2-methylenebicyclo[2.1.0]pentane endo-2-methylene-5-methylbicyclo[2.1.0]pentane S57

5,5-dimethylbicyclo[2.1.0]pent-2-ene syn-tricyclo[3.2.0.02,4]heptane bicyclo[4.2.0]octa-1,3,5,7-tetraene 2,4,6-octatriyne (1α,2α,5α,6α)-tricyclo[4.2.0.02,5]octa-3,7-diene (1α,2β,5β,6α)-tricyclo[4.2.0.02,5]octa-3,7-diene S58

bicyclo[2.2.2]octa-2,5,7-triene 2a,2b,4a,4b-tetrahydrocyclopropa[cd]pentalene pentacyclo[3.3.0.02,4.03,7.06,8]octane 7-methylenebicyclo[2.2.1]hepta-2,5-diene tricyclo[4.1.1.07,8]octa-2,4-diene cycloocta-1,5-dien-3-yne cycloocta-1,3-dien-6-yne S59

3-methylenetetracyclo[3.2.0.02,7.04,6]heptane 1,5-dihydropentalene 1-ethynyl-1-(1-propynyl)cyclopropane tetrakis(methylene)cyclobutane heptafulvene 5-methylenebicyclo[2.2.1]hept-2-ene 1,5-dimethyl-3-exo-methylenetricyclo[2.1.0.0]pentane S60

tricyclo[4.1.1.07,8]oct-3-ene 1-methylnorbornadiene 2-methylnorbornadiene tricyclo[4.1.1.07,8]oct-2-ene 6-methyltricyclo[4.1.0.02,7]hept-3-ene 1-methyltricyclo[4.1.0.02,7]hept-3-ene 7-methylenebicyclo[3.2.0]hept-1-ene S61

bicyclo[3.3.0]octa-2,6-diene 5-methyl-3H-1,2-dithiole-3-thione 3H-1,2-dithiole-3-thione, 4-methyl- dihydro-2(3h)-thiophenthione 2,2-dimethylthiirane 2-methylthietane 3-methylthietane S62

2-methyl-1,3-dithiacyclopentane 4-methyl-1,3-dithiolane 3-methyl-1,2-dithiolane 4-methyl-1,2-dithiolane trimethylthiirane 3,3-dimethylthietane 7-thiabicyclo[4.1.0]heptane S63

2-(1,1-dimethylethyl)thiirane thieno[3,2-b]thiophene thieno[2,3-b]thiophene thieno[3,4-b]thiophene dithio-p-benzoquinone benzodithiete methyloxirane S64

cyclopropylidenemethanone 2(3H)-furanone 1,4-dioxin 3(2H)-furanone cyclobutane-1,3-dione 1,2-cyclobutanedione 2,5-dihydrofuran S65

2-methyl-1-propen-1-one 3-methyleneoxetane 4-methylene-1,3-dioxolane α-trimethylethylene oxide 7-oxabicyclo[2.2.1]heptane 2-oxaspiro[3,3]heptane 1,2,4-triazine S66

1,2,3-triazine 2-aziridinecarbonitrile 1-azetine cyclopropanimine dimethylcyanamide 3,3-dimethyldiazirine 1-pyrazoline S67

2-pyrazoline azetidine 1-methylaziridine 5-(dimethylamino)tetrazole 3,3-dimethyldiaziridine cyanoallene 1,1-dicyanoethane S68

3-methyl-1,2,4-triazine 6-methyl-1,2,4-triazine 4-methyl-1,2,3-triazine pyrimidine, 4-amino-, 1h-imidazole, 1-methyl- 4-methylimidazole 4-methylpyrazole S69

2,5-dihydro-1H-pyrrole isopropyl isocyanide 1-methyl-5-aminopyrazole 1-methyl-3-aminopyrazole 1,1'-biaziridine N-methylazetidine 2-methyl-1,5-diazabicyclo[3.1.0]hexane S70

pyrrole-2-carbonitrile 1-methylcyclopropene-3-carbonitrile 1-methylcyclopropanecarbonitrile S71

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