Thermochemical studies of benzoylnitrene radical anion: The N-H bond dissociation energy in benzamide in the gas phase

Journal of Physical Chemistry A

Volumn 111, Issue 42, 2007, Pages 10712-10716

  Wijeratne, Neloni R ^a   Wenthold, Paul G ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDES; BENZAMIDYL RADICALS; COLLISION-INDUCED DISSOCIATION (CID); DISSOCIATION ENERGY;

AROMATIC HYDROCARBONS; CHEMICAL BONDS; DISSOCIATION; ELECTRON AFFINITY; PHASE TRANSITIONS;

NEGATIVE IONS;

EID: 35948980086     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp074255b     Document Type: Article

References (46)

1. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
2. Wenthold, P. G. Angew. Chem., Int. Ed. 2005, 44, 7171.
3. Tsang, W. Heats of Formation of Organic Free Radicals by Kinetic Methods. In Energetics of Organic Free Radicals; Simoes, M., Greenberg, J., Liebman, J. F., Eds.; Blackie Academic and Professional: London, 1996; p 22.
4. Ervin, K. M. Chem. Rev. 2001, 101, 391.
5. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
6. Goebbert, D. J.; Wenthold, P. G. Int. J. Mass Spectrom. 2006, 257, 1.
7. Bordwell, F. G.; Ji, G. Z. J. Am. Chem. Soc. 1991, 113, 8398.
8. Bordwell, F. G.; Harrelson, J. A.; Lynch, T. Y. J. Org. Chem. 1990, 55, 3337.
9. Bordwell, F. G.; Zhang, S.; Zhang, X.-M.; Liu, W.-Z. J. Am. Chem. Soc. 1995, 117, 7092.
10. Gomes, J. R. B.; Silva, M. D. M. C. R. d.; Silva, M. A. V. R. d. J. Phys. Chem. 2004, 108, 2119.
11. DePuy, C. H.; Bierbaum, V. M.; Flippin, L. A.; Grabowski, J. J.; King, G. K.; Schmitt, R. J.; Sullivan, S. A. J. Am. Chem. Soc. 1980, 102, 5012.
12. Marinelli, P. J.; Paulino, J. A.; Sunderlin, L. S.; Wenthold, P. G.; Poutsma, J. C.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1994, 130, 89.
13. Ervin, K. M.; Armentrout, P. B. J. Am. Chem. Soc. 1985, 83, 166.
14. Dalleska, N. F.; Honma, K.; Sunderlin, L. S.; Armentrout, P. B. J. Am. Chem. Soc. 1994, 116, 3519.
15. Schultz, R. H.; Crellin, K. C.; Armentrout, P. B. J. Am. Chem. Soc. 1991, 113, 8590.
16. Sunderlin, L. S.; Armentrout, P. B. Int. J. Mass Spectrom. Ion Processes 1989, 94, 149.
17. Muntean, F.; Armentrout, L. S. J. Chem. Phys. 2001, 115, 1213.
18. Rodgers, M. T.; Ervin, K. M.; Armentrout, L. S. J. Chem. Phys. 1997, 106, 4499.
19. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2003.
20. De Turi, V. F.; Ervin, K. M. J. Phys. Chem. A 1999, 103, 6911.
21. Iceman, C.; Armentrout, L. S. Int. J. Mass Spectrom. 2003, 222, 309.
22. Liu, J.; Mandel, S.; Hadad, C. M.; Platz, M. S. J. Org. Chem. 2004, 69, 8583.
23. Begtrup, M.; Nielsen, J.; Nygaard, L.; Samdal, S.; Sjogren, C. E.; Soerensen, G. O. Acta. Chemi. Scand., Ser. A 1988, 42 (8-9), 500.
24. McDonald, R. N.; Chowdhury, A. K.; Setser, D. W. J. Am. Chem. Soc. 1981, 103, 6599.
25. Pellerite, M. J.; Brauman, J. I. J. Am. Chem. Soc. 1981, 103, 676.
26. Travers, M. T.; Cowles, D. C.; Clifford, E. P.; Ellison, G. B. J. Am. Chem. Soc. 1992, 114, 8699.
27. Travers, M. J.; Cowles, D. C.; Clifford, E. P.; Ellison, G. B. J. Chem. Phys. 1999, 111, 5349.
28. acid = 1472 ± 2 kJ/mol, from ref 30 and the acidity difference of 49 between pyrrole and 1,2,3-triazole reported in ref 31.
29. Gianola, A. J.; Ichino, T.; Hoenigman, R. L.; Kato, S.; Bierbaum, V. M.; Lineberger, W. C. J. Phys. Chem. A 2004, 108, 10326.
30. Catalan, J.; Claramunt, R. M.; Elguero, J.; Laynez, J.; Menendez, M.; Anvia, F.; Quian, J. H.; Taagepera, M.; Taft, R. W. J. Am. Chem. Soc. 1988, 110, 4105.
31. Fujio, M.; McIver, R. T. J.; Taft, R. W. J. Am. Chem. Soc. 1981, 103, 4017.
32. Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1988, 110, 607.
33. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
34. Denisov, E. T.; Tumanov, V. E. Russ. Chem. Rev. 2005, 74, 825.
35. Woo, H.-K.; Wang, X.-B.; Kiran, B.; Wang, L.-S. J. Phys. Chem. A 2005, 109, 11395.
36. Bartmess, J. E. Negative Ion Energetics Data. In NIST Chemistry WebBook; NIST Standard Reference Database No. 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, June 2005 (http://webbook.nist.gov).
37. Dawson, J. H. J.; Nibbering, N. M. M. Int. J. Mass Spectrom. Ion Phys. 1980, 33, 3.
38. Dawson, J. H. J.; Jennings, K. R. J. Chem. Soc., Faraday Trans. 1976, 72, 700.
39. Lee, J.; Grabowski, J. J. Chem. Rev. 1992, 92, 1611.
40. Yang, X.; Zhang, X.; Castelman, A. W. J. J. Phys. Chem. 1991, 95, 8520.
41. Snodgrass, J. T.; Roehl, G M.; Van Koppen, P. A. M.; Palke, W. E.; Bowers, M. T. J. Chem. Phys. 1990, 92, 5935.
42. Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Neutral Thermochemical Data. In NlST Chemistry WebBook; NIST Standard Reference Database No. 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, June 2005 (http:// webbook.nist.gov).
43. Brown, S. S.; Berghout, H. L.; Crim, F. F. J. Chem. Phys. 1996, 105, 8103.
44. Chase, M. W., Jr. J. Phys. Chem. Ref. Data, Monogr. 9 1998, 1.
45. Bradforth, S. E.; Kim, E. H.; Arnold, D. W.; Neumark, D. M. J. Chem. Phys. 1993, 98, 800.
46. Kong, J.; et al. J. Comput. Chem. 2000, 21, 1532.