Substituent effects in tautomerism. Part I. Acyl- and sulphonylamidines
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 546-552
- https://doi.org/10.1039/p29740000546
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–CRN–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.Keywords
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