Issue 5, 1974

Substituent effects in tautomerism. Part I. Acyl- and sulphonylamidines

Abstract

The tautomerism of acyl- and sulphonyl-amidines is reviewed. The structures of the cations of mobile and fixed forms of acetyl-, benzoyl-, mesyl-, and tosyl-amidines are established by u.v. spectroscopy. Quantitative pKa measurements demonstrate that the H2N–CR[double bond, length half m-dash]N–Y form predominates for all series with KTca. 30 for the acyl- and ca. 107 for the sulphonyl compounds.

These results are compared with the tautomerism of 2-acylamino- and 2-sulphonamido-pyridines, and differences in tautomeric behaviour are rationalised.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1974, 546-552

Substituent effects in tautomerism. Part I. Acyl- and sulphonylamidines

S. Chua, M. J. Cook and A. R. Katritzky, J. Chem. Soc., Perkin Trans. 2, 1974, 546 DOI: 10.1039/P29740000546

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