Equilibrium constants between boron trifluoride etherate and carbonyl compounds in chloroform solution

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2813-2815

  Gajewski, J J ^a   Ngernmeesri, P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000344751     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000164k     Document Type: Article

References (18)

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9. Fratiello, A.; Onak, T. P.; Schuster, R. E. J. Am. Chem. Soc. 1968, 90, 0. 1194. See also the following: Gillespie, R. J.; Hartman, J. S. Can. J. Chem. 1968, 46, 2147. Childs,. R F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801.
10. Fratiello, A.; Onak, T. P.; Schuster, R. E. J. Am. Chem. Soc. 1968, 90, 0. 1194. See also the following: Gillespie, R. J.; Hartman, J. S. Can. J. Chem. 1968, 46, 2147. Childs,. R F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801.
11. (a) Gaussian 98. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh. PA, 1998.
12. 3 with the resources available.
13. (c) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper Collis Publishers: New York, 1987; Chapter 2, Appendix 2.
14. Reference 7, Chapter 4, Table 4.19.
15. For an excellent summary, see: Abraham, M. H.; Grellier, P. L.; Abboud, J.-L. M.; Doherty, R. M.; Taft, R. W. Can, J. Chem. 1988, 66, 2673.
16. Gajewski, J. J. J. Org. Chem. 1992, 57, 5500. Gajewski, J. J.; Brichford, N. J. In Structure and Reactivity in Aqueous Solution; Cramer, C. J., Truhlar, D. G., Eds.; ACS Symposium Series #568; American Chemical Society: Washington, DC, 1994; p 229.
17. Gajewski, J. J. J. Org. Chem. 1992, 57, 5500. Gajewski, J. J.; Brichford, N. J. In Structure and Reactivity in Aqueous Solution; Cramer, C. J., Truhlar, D. G., Eds.; ACS Symposium Series #568; American Chemical Society: Washington, DC, 1994; p 229.
18. It may be of interest to note that complexation of hydrogen ion with individual solvent molecules in the gas phase reported in ref 5 can be well-correlated with the combination of β′ and the Kirkwood-Onsager function of dielectric, i.e., (∈ - 1)/(2∈ + 1) and the polarizability parameters of ref 7, Chapter 2, Table 2.15, footnote c. However, complexation of lithium and potassium cation with individual solvent molecules in the gas phase (ref 5) can be well-correlated with only the combination of the Kirkwood-Onsager function and the polarizability parameters, that is, β or β′ factors do not contribute in these two cases.