The proton affinities of imines and the heats of formation of immonium ions investigated with composite ab initio methods

Journal of the American Chemical Society

Volumn 121, Issue 25, 1999, Pages 6002-6009

  Hammerum, Steen ^a   Sølling, Theis I ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; ION; PROTON;

ANALYTIC METHOD; ARTICLE; CALCULATION; ENERGY; HEAT; HYBRIDIZATION; ISOMER; PROTON TRANSPORT; SYNTHESIS;

EID: 0033618112     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984077n     Document Type: Article

References (57)

1. Aue, D. H.; Bowers, M. T. In Gas Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1979; Vol. 2, pp 1-51.
2. Smith, P. A. S. The Chemistry of Open-Chain Organic Nitrogen Compounds; W. A. Benjamin: New York, 1965; Vol. 1, pp 297-306.
3. Peerboom, R. A. L.; Ingemann, S.; Nibbering, N. M. M.; Liebman, J. F. J. Chem. Soc., Perkin Trans. 2 1990, 1825.
4. Bouchoux, G.; Salpin, J.-Y. J. Phys. Chem. 1996, 100, 16555.
5. Lossing, F. P.; Lam, Y.-T.; Maccoll, A. Can. J. Chem. 1981, 59, 2228.
6. (a) Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622.
7. (b) Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
8. Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1993, 98, 1293.
9. Curtiss, L. A.; Redfern, P. C.; Smith, B. J.; Radom, L. J. Chem. Phys. 1996, 104, 5148.
10. (a) Petersson, G. A.; Tensfeldt, T. G.; Montgomery, J. A. J. Chem. Phys. 1991, 94, 6091.
11. (b) Montgomery, J. A.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1994, 101, 5900.
12. Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. J. Chem. Phys. 1996, 104, 2598.
13. Ochterski, J. W.; Petersson, G. A.; Wiberg, K. J. Am. Chem. Soc. 1995, 117, 11299.
14. (a) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885.
15. (b) Smith, B. J.; Radom, L. Chem. Phys. Lett. 1994, 231, 345.
16. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
17. Hammerum, S. Int. J. Mass Spectrom. Ion Processes 1997, 165, 63.
18. Smith, B. J.; Radom, L. J. Phys. Chem. 1995, 99, 6468.
19. Seasholtz, M. B.; Thompson, T. B.; Rondan, N. G. J. Phys. Chem. 1995, 99, 17838.
20. (a) Holmes, J. L.; Fingas, M.; Lossing, F. P. Can. J. Chem. 1981, 59, 80.
21. (b) Holmes, J. L.; Lossing, F. P. Can. J. Chem. 1982, 60, 2365.
22. Bachiri, M.; Mouvier, G.; Carlier, P.; Dubois, J. E. J. Chim. Phys. 1980, 77, 899.
23. 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. Vol. 1.
24. Maccoll, A. Org. Mass Spectrom. 1985, 20, 715.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski, 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, rev D3, SGI; Gaussian, Inc.: Pittsburgh, PA.
26. Our calculated atom energies are identical to those reported for the G2(MP2) and G2(MP2, SVP) procedures (refs 7 and 8) and for the CBS-Q method (refs 10 and 11), except for a 0.03 mH difference for the oxygen atom CBS-Q energy.
27. Nicolaides, A.; Rauk, A.; Glukhovtsev, M. N.; Radom, L. J. Phys. Chem. 1996, 100, 17460.
28. Wagman, D. D.; Evans, W. H.; Parker, V. B.; Schumm, R. H.; Halow, I.; Bailey, S. B.; Churney, K. L.; Nuttall, R. L. J. Phys. Chem. Ref. Data 1982, 11, Suppl. Vol. 2.
29. Press, W. H.; Flannery, B. P.; Tenkolsky, S. A.; Vetterling, W. T. Numerical Recipes in C: The Art of Scientific Computing; Cambridge University Press: Cambridge, UK, 1988.
30. Benson, S. W. Thermochemical Kinetics; Wiley: New York, 1976.
31. Cohen, N.; Benson, S. W. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1992; p 215.
32. Benson, S. W.; Cruickshank, F. R.; Golden, D. M.; Haugen, G. R.; O'Neal, H. E.; Rodgers, A. S.; Shaw, R.; Walsh, R. Chem. Rev. 1969, 69, 279.
33. Slayden, S. W.; Liebman, J. F. In The chemistry of double-bonded functional groups; Patai, S., Ed.; Wiley: Chichester, 1997; Supplement A3, p 537.
34. Wiberg, K. B.; Nakaji, D. Y.; Morgan, K. M. J. Am. Chem. Soc. 1993, 115, 3527.
35. Pedley, J. B.; Naylor, R. D., Kirby, S. R. Thermochemical Data of Organic Compounds; Chapman and Hall: London, 1986.
36. -1).
37. (a) Hine, J.; Yeh, C. Y. J. Am. Chem. Soc. 1967, 89, 2669.
38. (b) Party, K. A. W.; Robinson, P. J.; Sainsbury, P. J.; Waller, M. J. J. Chem. Soc. B 1970, 700.
39. (c) Fraser, R. R.; Banville, J. J. Chem. Soc., Chem. Commun. 1979, 47.
40. Lammertsmaa, K.; Prasad, B. V. J. Am. Chem. Soc. 1994, 116, 642.
41. Karabatsos, G. J.; Lande, S. S. Tetrahedron 1968, 24, 3907.
42. Karabatsos, G. J.; Fenoglio, D. J. Top. Stereochem. 1970, 5, 167.
43. Dorigo, A. E.; Pratt, D. W.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 6591.
44. Traeger, J. C.; McLoughlin, R. G. J. Am. Chem. Soc. 1981, 103, 3647.
45. Hammerum, S.; Derrick, P. J. J. Chem. Soc., Chem. Commun. 1985, 996.
46. (a) Kagan, H. Organic Stereochemistry; Edward Arnold: London, 1979.
47. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 616-618.
48. Cohen, N.; Benson, S. W. Chem. Rev. 1993, 93, 2419.
49. Hammerum, S., manuscript in preparation.
50. Holmes, J. L.; Lossing, F. P.; Mayer, P. M. Chem. Phys. Lett. 1992, 198, 211.
51. Smith, B. J.; Pople, J. A.; Curtiss, L. A.; Radom, L. Aust. J. Chem. 1992, 45, 285.
52. Dyke, J. M.; Lee, E. P. F.; Niavaran, M. H. Z. Int. J. Mass Spectrom. Ion Processes 1989, 94, 221.
53. Tsang, W. In Energetics of Organic Free Radicals; Simões, J. A. M., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic: London, 1996; p 22.
54. Traeger, J. C.; Kompe, B. M. In Energetics of Organic Free Radicals; Simões, J. A. M., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic: London, 1996; p 59.
55. Suarez, D.; Sordo, T. L. J. Phys. Chem. A. 1997, 101, 1561.
56. (a) Hunter, E. P.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
57. (b) Hunter, E. P.; Lias, S. G. In NIST chemistry webbook [computer file]; Mallard, W. G., Linstrom, P. J., Eds.; NIST Standard Reference Database 69; National Institute of Standards and Technology: Gaithersburg MD, August 1997 (http://webbook.nist.gov).