Issue 2, 1990

Amidines. Part 30. Influence of substitution at amino nitrogen atom on pKavalues of N2-phenylacetamidines and N2-phenylformamidines

Abstract

A series of N2-phenylanylacetamidines and N2-phenylformamidines (22 compounds) containging variable substitutents at amino nitrogen atom have been synthesized, and their pKavalues in 95.6% ehonal (azeotrope) measured. The pKa values obtained for N1-methayl-N1,N2-diphenylaceamidines were correlated with Hammett type constants. Applicability of various σ values is discussed and it is shown that for substituents on the phenyl ring at amino nitrogen atom σ0values should be used. It is also shown that the pKa values of amidines correlate well with the pKavalues of corresponding secondary amines, and that this correlation can serve in the prediction of the pKa of amidine.

Comparison of the correlations obtained for studied acetamidines and formamedines indicates that sensitivity of the amidino group to substitution at the amino nitrogen atom depends to a certain degree on the substituent at the functional carbon atom.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1990, 311-314

Amidines. Part 30. Influence of substitution at amino nitrogen atom on pKavalues of N2-phenylacetamidines and N2-phenylformamidines

J. Oszczapowicz, W. Krawczyk and P. Łyźwiński, J. Chem. Soc., Perkin Trans. 2, 1990, 311 DOI: 10.1039/P29900000311

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