Thermochemistry of CH3CN, CH3NC, and their cyclic isomers and related radicals, cations, and anions: Some curious discrepancies between theory and experiment

Journal of Physical Chemistry A

Volumn 102, Issue 35, 1998, Pages 7074-7080

  Mayer, Paul M ^a,b   Taylor, Mark S ^a   Wong, Ming Wah ^a,c   Radom, Leo ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF OTTAWA   (Canada)

^c NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000865949     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp982272i     Document Type: Article

References (59)

1. (a) Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
2. For reviews of the application of G2 theory, see: (b) Curtiss, L. A.; Raghavachari, K. In Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy; Langhoff, S. R., Ed.; Kluwer Academic Publishers: Dordrecht, 1995. (c) Raghavachari, K.; Curtiss, L. A. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995.
3. For reviews of the application of G2 theory, see: (b) Curtiss, L. A.; Raghavachari, K. In Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy; Langhoff, S. R., Ed.; Kluwer Academic Publishers: Dordrecht, 1995. (c) Raghavachari, K.; Curtiss, L. A. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995.
4. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
5. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
6. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
7. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
8. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
9. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
10. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
11. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
12. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
13. For recent examples of the application of G2 theory to the derivation of thermochemical properties, see: (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. (b) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (c) Wong, M. W.; Radom, L. J. Am. Chem. Soc. 1993, 115, 1507. (d) Bauschlicher, C. W.; Partridge, H. Chem. Phys. Lett. 1995, 245, 158. (e) Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838. (f) Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327. (g) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063. (h) Armstrong, D. A.; Yu, D.; Rauk, A. J. Phys. Chem. A 1997, 101, 4761. (i) Mayer, P. M.; Glukhovtsev, M. N.; Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 12889. (j) Mayer, P. M.; Radom, L. J. Phys. Chem. A 1998, 102, 4918.
14. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 17 (Suppl. 1).
15. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
16. (a) Moran, S.; Ellis, H. B.; DeFrees, D. J.; McLean, A. D.; Ellison, G. B. J. Am. Chem. Soc. 1987, 109, 5996.
17. (b) Moran, S.; Ellis, H. B.; DeFrees, D. J.; McLean, A. D.; Paulson, S. E.; Ellison, G. B. J. Am. Chem. Soc. 1987, 109, 6004.
18. (c) Filley, J.; DePuy, C. H.; Bierbaum, V. J. Am. Chem. Soc. 1987, 109, 5992.
19. (d) Matimba, H. E. K.; Crabbendam, A. M.; Ingemann, S.; Nibbering, N. M. M. Int. J. Mass Spectrom. Ion Processes 1992, 114, 85.
20. (e) Holmes, J. L.; Lossing, F. P.; Mayer, P. M. Chem. Phys. Lett. 1993, 212, 134, and references therein.
21. (f) Holmes, J. L.; Mayer, P. M. J. Phys. Chem. 1995, 99, 1366.
22. (a) Pasto, D. J. J. Am. Chem. Soc. 1988, 110, 8164.
23. (b) Leroy, G.; Sana, M.; Wilante, C. J. Mol. Struct. (THEOCHEM) 1991, 228, 37.
24. (c) Lehd, M.; Jensen, F. J. Org. Chem. 1991, 56, 884.
25. (d) Jursic, B. S.; Timberlake, J. W.; Engel, P. S. Tetrahedron Lett. 1996, 37, 6473.
26. (e) Korth, H.-G.; Sicking, W. J. Chem. Soc., Perkin Trans. 2 1997, 715.
27. Bordwell, F. G.; Zhang, X.-M.; Alnajjar, M. S. J. Am. Chem. Soc. 1992, 114, 7623.
28. (a) Smith, D. Chem. Rev. 1992, 92, 1473.
29. (b) Herbst, E. Annu. Rev. Phys. Chem. 1995, 46, 27.
30. Horn, M.; Oswald, M.; Oswald, R.; Botschwina, P. Ber. Bunsen-Ges. Phys. Chem. 1995, 99, 323.
31. (a) Shea, D. A.; Steenvoorden, R. J. J. M.; Chen, P. J. Phys. Chem. A 1997, 101, 9728.
32. (b) Thorn, R. P.; Monks, P. S.; Stief, L. J.; Kuo, S. C.; Zhang, Z.; Ross, S. K.; Klemm, R. B. J. Phys. Chem. A 1998, 102, 846.
33. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B G.; Robb, M. A.; Cheesman, J. R.; Keith, T.; Petersson, A.; Montgomery, A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94; Gaussian Inc.; Pittsburgh, PA, 1995.
35. Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1995, 103 4192.
36. Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. J. Chem. Phys. 1996 104, 2598.
37. Mayer, P. M.; Parkinson, C. J.; Smith, D. M.; Radom, L. J. Chem. Phys. 1998, 108, 604.
38. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
39. Nicolaides, A.; Rauk, A.; Glukhovtsev, M. N.; Radom, L. J. Phys. Chem. 1996, 100, 17460.
40. Wagman, D. D.; Evans, W. H.; Parker, V. B.; Schumm, R. H.; Halow, I.; Bailey, S. M.; Churney, K. L.; Nuttall, R. L. J. Phys. Chem. Ref. Data 1982, 11 (Suppl. 2).
41. 3NC, see: (a) Delbeq. F. J. Mol. Struct. 1983, 93, 353. (b) Dixon, D. A.; Eades, R. A.; Frey, R.; Gassman, P. G.; Hendewerk, M. L.; Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 3885. (c) Palmer, M. H. J. Mol. Struct. (THEOCHEM) 1989, 200, 1. (d) Gutsev, G. L.; Sobolewski, A. L.; Adamowicz, L. Chem. Phys. 1995, 196, 1, and references therein.
42. 3NC, see: (a) Delbeq. F. J. Mol. Struct. 1983, 93, 353. (b) Dixon, D. A.; Eades, R. A.; Frey, R.; Gassman, P. G.; Hendewerk, M. L.; Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 3885. (c) Palmer, M. H. J. Mol. Struct. (THEOCHEM) 1989, 200, 1. (d) Gutsev, G. L.; Sobolewski, A. L.; Adamowicz, L. Chem. Phys. 1995, 196, 1, and references therein.
43. 3NC, see: (a) Delbeq. F. J. Mol. Struct. 1983, 93, 353. (b) Dixon, D. A.; Eades, R. A.; Frey, R.; Gassman, P. G.; Hendewerk, M. L.; Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 3885. (c) Palmer, M. H. J. Mol. Struct. (THEOCHEM) 1989, 200, 1. (d) Gutsev, G. L.; Sobolewski, A. L.; Adamowicz, L. Chem. Phys. 1995, 196, 1, and references therein.
44. 3NC, see: (a) Delbeq. F. J. Mol. Struct. 1983, 93, 353. (b) Dixon, D. A.; Eades, R. A.; Frey, R.; Gassman, P. G.; Hendewerk, M. L.; Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 3885. (c) Palmer, M. H. J. Mol. Struct. (THEOCHEM) 1989, 200, 1. (d) Gutsev, G. L.; Sobolewski, A. L.; Adamowicz, L. Chem. Phys. 1995, 196, 1, and references therein.
45. (a) Landolt-Börnstein, New Series, Vol. II/23 (3,152) (polyatomic molecules): Kuchitsu, K., Ed. Structure Data of Free Polyatomic Molecules; 1995.
46. (b) Landolt-Börnstein, New Series, Vol. II/15 (3,282) (polyatomic molecules): Hellwege, K.-H., Hellwege, A. M., Eds. Structure Data of Free Polyatomic Molecules; 1987.
47. See also: Byun, Y.-G.; Saebo, S.; Pittman, C. U. J. Am. Chem. Soc. 1991, 113, 3689, and references therein.
48. See also references 5a (1) and 5b (2), and references therein.
49. Saito, S.; Yamamoto, S. J. Chem. Phys. 1997, 107, 1732.
50. See, for example: (a) Glukhovtsev, M. N.; Laiter, S.; Pross, A. J. Phys. Chem. 1996, 100, 17801. (b) Kass, S. R.; Merrill, G. N. J. Am. Chem. Soc. 1997 119, 12322.
51. See, for example: (a) Glukhovtsev, M. N.; Laiter, S.; Pross, A. J. Phys. Chem. 1996, 100, 17801. (b) Kass, S. R.; Merrill, G. N. J. Am. Chem. Soc. 1997 119, 12322.
52. 2N cations, see: (a) Swanton, D. J.; Bacskay, G. B.; Willet, G. D.; Hush, N. S. J. Mol. Struct. (THEOCHEM) 1983, 91, 313. (b) Harland, P. W.; Maclagan, R. G. A. R.; Schaefer, H. F. J. Chem. Soc., Faraday Trans. 2 1989, 85, 187.
53. 2N cations, see: (a) Swanton, D. J.; Bacskay, G. B.; Willet, G. D.; Hush, N. S. J. Mol. Struct. (THEOCHEM) 1983, 91, 313. (b) Harland, P. W.; Maclagan, R. G. A. R.; Schaefer, H. F. J. Chem. Soc., Faraday Trans. 2 1989, 85, 187.
54. Bartmess, J. E.; Scott, J. A.; McIver, R. T. J. Am. Chem. Soc. 1979, 101, 6046.
55. -1.
56. Joshi, R. M. J. Macramol. Sci., Chem. 1982, A18, 861.
57. 30
58. 2 surface, see: Watch S. P.; Partridge, H Chem. Phys. Lett. 1995, 233, 331.
59. 2 surface, see: Watch S. P.; Partridge, H Chem. Phys. Lett. 1995, 233, 331.