Abstract
Taft and Kamlet's α-scale of solvent hydrogen bond donation ability is reexamined with regard to its correlations with three widely used polarity scales: Dimroth and Reichardt's E T (30), Kosower's Z and Mayer's A N , as well as with the αm values of the solvents when present as monomeric solutes. The correlation with E T serves to extend the solvent α-scale according to the expression:
where s, b, a, d, π*, δ, and β have their usual meanings in the context of the Taft and Kamlet scales.
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References
R. W. Taft and M. J. Kamlet,J. Am. Chem. Soc. 98, 2886 (1976).
M. J. Kamlet and R. W. Taft,J. Am. Chem. Soc. 98, 377 (1976).
M. J. Kamlet and R. W. Taft,Acta Chem. Scand. B 39, 611 (1985).
M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham, and R. W. Taft,J. Org. Chem. 48, 2877 (1983).
R. W. Taft and M. J. Kamlet,J. Chem. Soc., Perkin Trans. II 1723 (1979).
K. Dimroth, C. Reichardt, T. Siepmann, and F. Bohlmann,Liebigs Ann. Chem. 661, 1 (1966).
C. Reichardt,Solvents and Solvent Effects in Organic Chemistry, 2nd edn., (VCH, Weinheim, 1988).
M. H. Abraham, P. L. Grellier, V. Prior, P. P. Duce, J. J. Morris, and P. J. Taylor,J. Chem. Soc., Perkin Trans. II, 699 (1989).
M. J. Kamlet, R. M. Doherty, M. H. Abraham, Y. Marcus, and R. W. Taft,J. Phys. Chem. 92, 5244 (1988).
Y. Marcus,J. Solution Chem. 13, 599 (1984).
M. H. Abraham, G. J. Buist, P. L. Grellier, R. A. McGill, D. V. Prior, S. Oliver, E. Turner, J. J. Morris, P. J. Taylor, P. Nicolet, P.-C. Maria, J.-F. Gal, J.-L. M. Abbound, R. M. Doherty, M. J. Kamlet, W. J. Shuley, and R. W. Taft,J. Phys. Org. Chem. 2, 540 (1989).
E. M. Kosower,J. Am. Chem. Soc. 80, 5253 (1958): E. M. Kosower,An Introduction to Physical Organic Chemistry (Wiley, New York, 1968).
U. Mayer, V. Gutmann, and W. Gerger,Monatsh. Chem. 106, 1235 (1975); U. Mayer,Stud. Phys. Theor. Chem. 27, 219 (1983).
K. Medda, M. Pal, and S. Bagchi,J. Chem. Soc., Faraday Trans. I 84, 1501 (1988).
J. Hormadaly and Y. Marcus,J. Phys. Chem. 83, 2843 (1979).
U. Mayer, personal communication, 1991.
Y. Migron and Y. Marcus,J. Phys. Org. Chem. 4, 370 (1991).
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Marcus, Y. The effectiveness of solvents as hydrogen bond donors. J Solution Chem 20, 929–944 (1991). https://doi.org/10.1007/BF01074953
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DOI: https://doi.org/10.1007/BF01074953