Estimated gas-phase standard state enthalpies of formation for organic compounds using the gaussian-4 (G4) and W1BD theoretical methods

Journal of Chemical and Engineering Data

Volumn 55, Issue 11, 2010, Pages 5359-5364

  Rayne, Sierra ^b   Forest, Kaya ^a  

^a Ecologica Research   (Canada)

^b OKANAGAN UNIVERSITY COLLEGE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COMPOSITE METHOD; CONFORMATIONAL COMPLEXITY; ENTHALPIES OF FORMATION; EXPERIMENTAL DATA; GAS-PHASE STANDARD; GAUSSIANS; HETEROATOMS;

FUNCTIONAL GROUPS;

ENTHALPY;

EID: 78449307774     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je100768s     Document Type: Article

References (44)

1. Cramer, C. J. Essentials of computational chemistry: Theories and models; Wiley: New York, 2004.
2. Brown, M. E. and Gallagher, P. K. Handbook of thermal analysis and calorimetry: Recent advances, techniques and applications; Elsevier: New York, 2007.
3. Curtiss, L. A.; Jones, C.; Trucks, G. W.; Raghavachari, K.; Pople, J. A. Gaussian-1 theory of molecular energies for second-row compounds J. Chem. Phys. 1990, 93, 2537-2545
4. Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. Gaussian-1 theory: A general procedure for prediction of molecular energies J. Chem. Phys. 1989, 90, 5622-5629
5. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. Gaussian-2 theory for molecular energies of first- and second-row compounds J. Chem. Phys. 1991, 94, 7221-7230
6. Curtiss, L. A.; Raghavachari, K.; Pople, J. A. Gaussian-2 theory using reduced Moller-Plesset orders J. Chem. Phys. 1993, 98, 1293-1298
7. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. Gaussian-3 (G3) theory for molecules containing first and second-row atoms J. Chem. Phys. 1998, 109, 7764-7776
8. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-3 theory using density functional geometries and zero-point energies J. Chem. Phys. 1999, 110, 7650-7657
9. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Rassolov, V.; Pople, J. A. Gaussian-3 theory using reduced Moller-Plesset order J. Chem. Phys. 1999, 110, 4703-4709
10. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. Assessment of Gaussian-2 and density functional theories for the computation of enthalpies of formation J. Chem. Phys. 1997, 106, 1063-1079
11. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. Assessment of Gaussian-3 and density functional theories for a larger experimental test set J. Chem. Phys. 2000, 112, 7374-7383
12. Bond, D. Computational methods in organic thermochemistry. 1. Hydrocarbon enthalpies and free energies of formation J. Org. Chem. 2007, 72, 5555-5566
13. Bond, D. Computational methods in organic thermochemistry. 2. Enthalpies and free energies of formation for functional derivatives of organic hydrocarbons J. Org. Chem. 2007, 72, 7313-7328
14. Bond, D. Computational methods in organic chemistry. 3. Correction of computed enthalpies for multiple conformations J. Phys. Chem. A 2008, 112, 1656-1660
15. Nicolaides, A.; Radom, L. An evaluation of the performance of G2, G2(MP2) and G2(MP2, SVP) theories for heats of formation and heats of reaction in the case of "large" hydrocarbons Mol. Phys. 1996, 88, 759-765
16. Notario, R.; Castano, O.; Abboud, J. L. M.; Gomperts, R.; Frutos, L. M.; Palmeiro, R. Organic thermochemistry at high ab initio levels. 1. A G2(MP2) and G2 study of cyclic saturated and unsaturated hydrocarbons (including aromatics) J. Org. Chem. 1999, 64, 9011-9014
17. 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
18. 16 alkanes J. Phys. Chem. A 2000, 104, 5850-5854
19. Haworth, N. L.; Smith, M. H.; Bacskay, G. B.; Mackie, J. C. Heats of formation of hydrofluorocarbons obtained by Gaussian-3 and related quantum chemical computations J. Phys. Chem. A 2000, 104, 7600-7611
20. Gomes, J. R. B.; Ribeiro da Silva, M. A. V. Thermochemistry of small organosulfur compounds from ab initio calculations J. Phys. Chem. A 2004, 108, 11684-11690
21. Blanquart, G.; Pitsch, H. Thermochemical properties of polycyclic aromatic hydrocarbons (PAH) from G3MP2B3 calculations J. Phys. Chem. A 2007, 111, 6510-6520
22. Taskinen, E.; Taskinen, A. Proximity effects of oxygen atoms on the enthalpies of formation of simple diethers: A computational G3(MP2)//B3 study J. Phys. Org. Chem. 2008, 21, 449-456
23. Taskinen, E. Enthalpies of formation and isomerization of aromatic hydrocarbons and ethers by G3(MP2)//B3LYP calculations J. Phys. Org. Chem. 2009, 22, 632-642
24. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-4 theory J. Chem. Phys. 2007, 126, 84108-84112
25. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-4 theory using reduced order perturbation theory J. Chem. Phys. 2007, 127, 124105-124108
26. Rayne, S.; Forest, K. Gas phase isomerization enthalpies of organic compounds: A semiempirical, density functional theory, and ab initio post-Hartree-Fock theoretical study J. Mol. Struct.: THEOCHEM 2010, 948, 102-107
27. 2 n (n = 1-6) isomers J. Mol. Struct.: THEOCHEM 2010, 948, 111-112
28. 2 chlorofluorocarbons and hydrochlorofluorocarbons J. Mol. Struct.: THEOCHEM 2010, 953, 47-48
29. Dorofeeva, O. V.; Ryzhova, O. N. Enthalpies of formation of β-alanine, sarcosine, and 4-aminobutanoic acid from quantum chemical calculations J. Chem. Thermodyn. 2010, 42, 1056-1062
30. Mayhall, N. J.; Raghavachari, K.; Redfern, P. C.; Curtiss, L. A. Investigation of Gaussian-4 theory for transition metal thermochemistry J. Phys. Chem. A 2009, 113, 5170-5175
31. Martin, J. M. L.; de Oliveira, G. Towards standard methods for benchmark quality ab initio thermochemistry-W1 and W2 theory J. Chem. Phys. 1999, 111, 1843-1856
32. 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
33. Barnes, E. C.; Petersson, G. A.; Montgomery, J. A.; Frisch, M. J.; Martin, J. M. L. Unrestricted coupled cluster and Brueckner doubles variations of W1 theory J. Chem. Theory Comput. 2009, 5, 2687-2693
34. Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. In NIST Chemistry WebBook, NIST standard reference database number 69; Linstrom, P. J.; Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 2010; http://webbook.nist.gov (accessed July 6, 2010).
35. Halgren, T. A. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94 J. Comput. Chem. 1996, 17, 490-519
36. Halgren, T. A. Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94 J. Comput. Chem. 1996, 17, 553-586
37. Halgren, T. A. Merck molecular force field. V. Extension of MMFF94 using experimental data, additional computational data, and empirical rules J. Comput. Chem. 1996, 17, 616-641
38. Halgren, T. A. MMFF VII. Characterization of MMFF94, MMFF94s, and other widely available force fields for conformational energies and for intermolecular-interaction energies and geometries J. Comput. Chem. 1999, 20, 730-748
39. Halgren, T. A.; Nachbar, R. B. Merck molecular force field. IV. Conformational energies and geometries for MMFF94 J. Comput. Chem. 1996, 17, 587-615
40. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
41. Allouche, A. R. Gabedit: A graphical user interface for computational chemistry softwares J. Comput. Chem. 2010, 10.1002/jcc.21600
42. Saeys, M.; Reyniers, M. F.; Marin, G. B.; Van Speybroeck, V.; Waroquier, M. Ab initio calculations for hydrocarbons: Enthalpy of formation, transition state geometry, and activation energy for radical reactions J. Phys. Chem. A 2003, 107, 9147-9159
43. van Speybroeck, V.; Gani, R.; Meier, R. J. The calculation of thermodynamic properties of molecules Chem. Soc. Rev. 2010, 39, 1764-1779
44. Cox, J. D.; Wagman, D. D.; Medvedev, V. A. CODATA key values for thermodynamics; Hemisphere: New York, NY, 1984.