The phenylcarbyne anion [3]

Journal of the American Chemical Society

Volumn 121, Issue 26, 1999, Pages 6310-6311

  Seburg, Randal A ^a,b   Hill, Brian T ^b   Jesinger, Rachel A ^b   Squires, Robert R ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BARBAN;

CONFORMATIONAL TRANSITION; ISOMERISM; LETTER; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033532871     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984026q     Document Type: Letter

References (33)

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7. Ervin, K. M.; Lineberger, W. C. In Advances in Gas-Phase Ion Chemistry; Adams, N. G., Babcock, L. M., Eds.; JAI Press: Greenwich, CT, 1992; Vol. 1.
8. For reactions of alkyldiazirines possessing β-hydrogens, see: (a) Anderson, K. K.; Kass, S. R. Tetrahedron Lett. 1989, 30, 3045. (b) Kroeker, R. L.; Kass, S. R. J. Am. Chem. Soc. 1990, 112, 9024.
9. For reactions of alkyldiazirines possessing β-hydrogens, see: (a) Anderson, K. K.; Kass, S. R. Tetrahedron Lett. 1989, 30, 3045. (b) Kroeker, R. L.; Kass, S. R. J. Am. Chem. Soc. 1990, 112, 9024.
10. 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. Operating conditions: P (He) = 0.4 Torr, flow (He) = 200 STP cm3/s.
11. 11
12. Karney, W. L.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 1378 and references therein.
13. Density functional calculations used the B3LYP and BVWN5 methods in conjunction with 6-31+G(d), cc-pVDZ basis sets for geometry optimizations and the aug-cc-pVTZ basis set for energies. B3LYP: Becke, A. D. J. Chem. Phys. 1993, 98, 5648; Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 78. BVWN5: Vosko, S. H.; Wilk, N.; Nusair, M. Can. J. Chem. 1980, 58, 1200.
14. Density functional calculations used the B3LYP and BVWN5 methods in conjunction with 6-31+G(d), cc-pVDZ basis sets for geometry optimizations and the aug-cc-pVTZ basis set for energies. B3LYP: Becke, A. D. J. Chem. Phys. 1993, 98, 5648; Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 78. BVWN5: Vosko, S. H.; Wilk, N.; Nusair, M. Can. J. Chem. 1980, 58, 1200.
15. Density functional calculations used the B3LYP and BVWN5 methods in conjunction with 6-31+G(d), cc-pVDZ basis sets for geometry optimizations and the aug-cc-pVTZ basis set for energies. B3LYP: Becke, A. D. J. Chem. Phys. 1993, 98, 5648; Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 78. BVWN5: Vosko, S. H.; Wilk, N.; Nusair, M. Can. J. Chem. 1980, 58, 1200.
16. (a) Salem, L.; Rowland, C. Angew. Chem., Intl. Ed. Engl. 1972, 11, 92.
17. (b) Michl, J. J. Am. Chem. Soc. 1996, 118, 3568.
18. The reported products come from 1 and not the phenyldiazirinyl anion since the intensity of the phenyldiazirinyl anion remains unchanged during the reactions.
19. (a) Bierbaum, V. M.; DePuy, C. H.; Shapiro, R. H. J. Am. Chem. Soc. 1977, 99, 5800.
20. (b) Kass, S. R.; Filley, J.; VanDoren, J. M.; DePuy, C. H. J. Am. Chem. Soc. 1986, 108, 2849.
21. Kass, S. R., personal communication of unpublished results.
22. DePuy, C. H.; Bierbaum, V. M.; Robinson, M. S.; Davico, G. E.; Gareyev, R. Tetrahedron, 1997, 53, 9847.
23. O'Hair, R. A. Mass Spectrom. Rev. 1991, 10, 133 and references therein.
24. Wenthold, P. G.; Hu, J.; Squires, R. R. J. Am. Chem. Soc. 1996, 118, 11865.
25. f (102.8 kca/mol) of phenylcarbene: Poutsma, J. C.; Nash, J. J.; Paulino, J. A.; Squires, R. R. J. Am. Chem. Soc. 1997, 119, 4686.
26. f (102.8 kca/mol) of phenylcarbene: Poutsma, J. C.; Nash, J. J.; Paulino, J. A.; Squires, R. R. J. Am. Chem. Soc. 1997, 119, 4686.
27. Hill, B. T.; Seburg, R. A.; Jesinger, R. A.; Squires, R. R., manuscript in preparation.
28. 1 state can be populated by the energy gained by complexation with the neutral molecule.
29. - (409.4 kcal/mol). Cycloheptatetraene was the conjugate acid used to compute the PA of 3.
30. (a) Stewart, J. H.; Shapiro, R. H.; DePuy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1977, 99, 7650.
31. (b) DePuy, C. H.; Bierbaum, V. M.; King, G. K.; Shapiro, R. H. J. Am. Chem. Soc. 1978, 100, 2921.
32. (c) Squires, R. R.; DePuy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1981, 103, 4256.
33. f for phenyldiazirine (87 kcal/mol) and 1 (105 kcal/mol), we obtain an enthalpy change of -7 kcal/mol for formation of 1 by reaction 1.