On the Heats of Formation of Alkanes
DOI:
https://doi.org/10.29356/jmcs.v53i3.990Keywords:
MM4, MP4, B3LYP, Dispersion Energy, Heats of FormationAbstract
A broad diverse test set of alkanes and cycloalkanes previously studied with MM4 calculations has had the heats of formation calculated by several different quantum mechanical methods: HartreeFock, MP2, and MP4, and also by B3LYP and B3LYP + dispersion energy. Overall, three computational methods (MM4, MP4, and B3LYP + dispersion) yield results that are generally of experimental accuracy. These results are analyzed and compared in some detail.
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References
1. Benson, S. W. Thermochemical Kinetics, Wiley, New York, 1976.
2. Burkert, U.; Allinger, N. L. Molecular Mechanics, American Chemical Society, Washington, D.C., 1982.
3. Engler, E. M.; Andose, J. D.; Schleyer, P. v. R. J. Am. Chem. Soc. 1973, 95, 8005.
4. Allinger, N. L.; Tribble, M. T.; Miller, M. A.; Wertz, D. H. J. Am. Chem. Soc. 1971, 93, 1637.
5. Allinger, N. L.; Hirsch, J. A.; Miller, M. A.; Tyminski, I. J.; and Van-Catledge, F. A. J. Am. Chem. Soc. 1968, 90, 1199.
6. (a) Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds, Academic Press, London, 1970. (b) Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd Edition, Chapman and Hall Ltd, 1986. (c) National Institute of Standards and Technology (NIST), webbook.nist.gov/chemistry. 7. Allinger, N. L.; Chen, K.; Lii, J.-H. J. Comput. Chem. 1996, 17, 642.
8. (a) Chen, K.-H.; Lii, J.-H.; Fan, Y.; Allinger, N. L. J. Comput. Chem. 2007, 28, 2391, and references therein. (b) Lii, J.-H. J. Phys. Chem. 2002, 106, 8667.
9. Redfern, P. C.; Zapol, P.; Curtiss, L. A.; Raghavachari, K. J. Phys. Chem. A 2000, 104, 5850, and papers cited therein.
10. (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory, John Wiley & Sons, Inc., New York, 1986. (b) Disch, R. L.; Schulman, J. M. J. Phys. Chem. 1996, 100, 3504. (c) Wheeler, S. E.; Houk, K. N.; Schleyer, P. v. R.; Allen, W. D. J. Am. Chem. Soc. 2009, 131, 2547.
11. (a) Wiberg, K. J. Comput. Chem., 5, 197 (1984); Wiberg, K. J. Org. Chem. 1985, 50, 5285. (b) Ibrahim, M. R.; Schleyer, P. v. R. J. Comput. Chem. 1985, 6, 157.
12. Allinger, N. L.; Schmitz, L. R.; Motoc, I.; Bender, C.; Labanowski, J. J. Am. Chem. Soc. 1992, 114, 2880. See especially the Supplementary Material.
13. (a) Allinger, N. L.; Sakakibara, K.; Labanowski, J. J. Phys. Chem. 1995, 99, 9603. (b) Schmitz, L. R.; Chen, K.-H.; Labanowski, J.; Allinger, N. L. J. Phys. Org. Chem. 2001, 14, 90.
14. (a) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1. (b) Chen, K.-H.; Allinger, N. L. J. Mol. Struct. (Theochem), 2002, 581, 215.
15. (a) Pitzer, K. S.; Gwinn, W. D. J. Chem. Phys. 1942, 10, 428. (b) Wertz, D. H.; Allinger, N. L. Tetrahedron, 1979, 35, 3.
16. Gaussian 03, Revision C.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, Jr., T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Wallingford CT, 2004.
17. (a) Labanowski, J.; Schmitz, L. R.; Chen, K.-H.; Allinger, N. L. J. Comput. Chem. 1998, 19, 1421. (b) Schmitz, L. R.; Chen, K.-H.; Labanowski, J.; Allinger, N. L. J. Phys. Org. Chem. 2001, 14, 90. 18. (a) Kristyan, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175. (b) Grimme, S. J. Chem. Phys., 124, 034108 (2006). (c) Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys. 2007, 9, 3397.
19. Verevkin, S. P.; Nolke, M.; Beckhaus, H.-D.; Ruechardt, C. J. Org. Chem. 1997, 62, 4683.
20. (a) Beckhaus, H.-D.; Ruechardt, C.; Lagerwall, D. R.; Paquette, L. A.; Wahl, F.; Prinzbach, H. J. Am. Chem. Soc. 1995, 117, 8885. (b) Beckhaus, H.-D.; Ruechardt, C.; Lagerwall, D. R.; Paquette, L. A.; Wahl, F. Prinzbach, H. J. Am. Chem. Soc. 1994, 116, 11775.
2. Burkert, U.; Allinger, N. L. Molecular Mechanics, American Chemical Society, Washington, D.C., 1982.
3. Engler, E. M.; Andose, J. D.; Schleyer, P. v. R. J. Am. Chem. Soc. 1973, 95, 8005.
4. Allinger, N. L.; Tribble, M. T.; Miller, M. A.; Wertz, D. H. J. Am. Chem. Soc. 1971, 93, 1637.
5. Allinger, N. L.; Hirsch, J. A.; Miller, M. A.; Tyminski, I. J.; and Van-Catledge, F. A. J. Am. Chem. Soc. 1968, 90, 1199.
6. (a) Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds, Academic Press, London, 1970. (b) Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd Edition, Chapman and Hall Ltd, 1986. (c) National Institute of Standards and Technology (NIST), webbook.nist.gov/chemistry. 7. Allinger, N. L.; Chen, K.; Lii, J.-H. J. Comput. Chem. 1996, 17, 642.
8. (a) Chen, K.-H.; Lii, J.-H.; Fan, Y.; Allinger, N. L. J. Comput. Chem. 2007, 28, 2391, and references therein. (b) Lii, J.-H. J. Phys. Chem. 2002, 106, 8667.
9. Redfern, P. C.; Zapol, P.; Curtiss, L. A.; Raghavachari, K. J. Phys. Chem. A 2000, 104, 5850, and papers cited therein.
10. (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory, John Wiley & Sons, Inc., New York, 1986. (b) Disch, R. L.; Schulman, J. M. J. Phys. Chem. 1996, 100, 3504. (c) Wheeler, S. E.; Houk, K. N.; Schleyer, P. v. R.; Allen, W. D. J. Am. Chem. Soc. 2009, 131, 2547.
11. (a) Wiberg, K. J. Comput. Chem., 5, 197 (1984); Wiberg, K. J. Org. Chem. 1985, 50, 5285. (b) Ibrahim, M. R.; Schleyer, P. v. R. J. Comput. Chem. 1985, 6, 157.
12. Allinger, N. L.; Schmitz, L. R.; Motoc, I.; Bender, C.; Labanowski, J. J. Am. Chem. Soc. 1992, 114, 2880. See especially the Supplementary Material.
13. (a) Allinger, N. L.; Sakakibara, K.; Labanowski, J. J. Phys. Chem. 1995, 99, 9603. (b) Schmitz, L. R.; Chen, K.-H.; Labanowski, J.; Allinger, N. L. J. Phys. Org. Chem. 2001, 14, 90.
14. (a) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1. (b) Chen, K.-H.; Allinger, N. L. J. Mol. Struct. (Theochem), 2002, 581, 215.
15. (a) Pitzer, K. S.; Gwinn, W. D. J. Chem. Phys. 1942, 10, 428. (b) Wertz, D. H.; Allinger, N. L. Tetrahedron, 1979, 35, 3.
16. Gaussian 03, Revision C.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, Jr., T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Wallingford CT, 2004.
17. (a) Labanowski, J.; Schmitz, L. R.; Chen, K.-H.; Allinger, N. L. J. Comput. Chem. 1998, 19, 1421. (b) Schmitz, L. R.; Chen, K.-H.; Labanowski, J.; Allinger, N. L. J. Phys. Org. Chem. 2001, 14, 90. 18. (a) Kristyan, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175. (b) Grimme, S. J. Chem. Phys., 124, 034108 (2006). (c) Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys. 2007, 9, 3397.
19. Verevkin, S. P.; Nolke, M.; Beckhaus, H.-D.; Ruechardt, C. J. Org. Chem. 1997, 62, 4683.
20. (a) Beckhaus, H.-D.; Ruechardt, C.; Lagerwall, D. R.; Paquette, L. A.; Wahl, F.; Prinzbach, H. J. Am. Chem. Soc. 1995, 117, 8885. (b) Beckhaus, H.-D.; Ruechardt, C.; Lagerwall, D. R.; Paquette, L. A.; Wahl, F. Prinzbach, H. J. Am. Chem. Soc. 1994, 116, 11775.
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