Amidines. Part 15. Influence of substitution at imino and amino nitrogen atoms on pKavalues of N1-methyl-N1N2-diarylacetamidines
- 1 January 1985
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 1087-1090
- https://doi.org/10.1039/p29850001087
Abstract
A series of 19 unreported N1-methyl-N1N2-diarylacetamidines containing two different substituents at the phenyl rings have been synthesized and their pKa values in 95.6% ethanol (azeotrope) measured. The pKa values have been correlated with σ° constants of the two substituents. The influence of substitution at either of the nitrogen atoms on basicity and on the regression coefficient is discussed, and it is shown that the pKa values of N1N2-diarylamidines can be predicted with satisfactory accuracy on the basis of the dual-substituent (planar) Hammett equation.Keywords
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