Carbon acidities of aromatic compounds

Journal of the American Chemical Society

Volumn 110, Issue 19, 1988, Pages 6297-6303

  Mautner, Michael Meot Ner ^a   Kafafi, Sherif A ^a  

^a NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845279403     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00227a003     Document Type: Article

References (12)

1. Lias, S. G.; Bartmess, J. E.; Liebman, J. E.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data, in press.
2. Cummings, J. B.; Kebarle, P. Can. J. Chem. 1978, 56, 1–9. (b) Kebarle, P.; Chowdhury, S. Chem. Rev. 1987, 87, 513, and references cited therein.
3. Taft, R. W.; Anvia, F.; Taagepera, M.; Catalan, J.; Elguero, J. J. Am. Chem. Soc. 1986, 108, 3237.
4. Frisch, M. J.; Binkley, J. S.; Schlegel, H. B.; Raghavachari, K.; Melius, C. F.; Martin, R. L.; Stewart, J. J. P.; Bobrowicz, F. W.; Rohlfing, C. M.; Kahn, L. R.; Defrees, D. J.; Seeger, R.; Whiteside, R. A.; Fox, D. J.; Fleuder, E. M.; Pople, J. A. Gaussian 86; Carnegie-Mellon Quantum Chemistry Publishing Unit: Pittsburgh, PA, 1984. (b) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902. (c) Dewar, M. J. S.; Dieter, K. M. J. Am. Chem. Soc. 1986, 108, 8075. (d) Fernandez, J.; Anguiano, J.; Villarrassa, J. J. Comput. Chem., in press.
5. Sieck, L. W.; Meot-Ner (Mautner), M. J. Phys. Chem. 1985, 89, 5552.
6. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab. Initio Molecular Orbital Theory; Wiley: New York, 1986. (b) Jordan, K. D.; Burrow, P. D. Chem. Rev. 1987, 87, 557.
7. Kafafi, S. A.; Krauss, M.; Meot-Ner (Mautner), M., to be submitted for publication. (b) To confirm this assumption, we have performed full-geometry optimizations on pyridine and the p-pyridinyl anion at the HF/6-31G level of theory. All C-H bond lengths were allowed to vary during the optimizations. For pyridine, the C-H bonds that are closest to the nitrogen were 0.001 Å shorter than the other C-H bonds. For the p-pyridinyl anion, this difference was 0.002 Å. The total HF/6-31G energies of pyridine and the p-pyridinyl anion differed from those given in Table II for these species by less than 0.2 kcal/mol.
8. Meot-Ner (Mautner), M.; Sieck, L. W., unpublished results.
9. Meot-Ner (Mautner), M.; Liebman, J. F.; Kafafi, S. A. J. Am. Chem. Soc., following paper in this issue.
10. Meot-Ner (Mautner), M.; Sieck, L. W. J. Phys. Chem. 1986, 90, 6687.
11. Liebman, J. F.; Politzer, P.; Rosen, D. C. Application of Electrostatic Potentials in Chemistry; Politzer, P., Truhlar, D. G., Eds.; Plenum: New York, 1981. (b) Pross, A.; Radom, L. Progress in Physical Organic Chemistry; Taft, R. W., Ed.; Wiley: New York, 1981; Vol. 13.
12. Siggel, M. R. F.; Thomas, T. D.; Saethre, L. J. J. Am. Chem. Soc. 1988, 110, 91.