Canadian Journal of Chemistry p. 1184 - 1188 (1986)
Update date:2022-08-25
Topics:
Oae, Shigeru
Kadoma, Yoshihito
The rates of aminolyses of p-toluenesulfonyl chloride with primary and tertiary amines have been determined both in acetonitrile and in ethanol.The Broensted plots of log krel again pKa' values fo amines (except hydrazine and 1,8-naphthyridine in acetonitrile) gave a good correlation when the aminolyses were carried out in acetonitrile.In ethanol, however, although Broensted plots with all tertiary amines show a good correlation, less basic hydrazine shows a higher reactivity than n-butylamine.The abnormal rate enhancement found with hydrazine is undoubtedly due to the α-effect, while with 1,8-naphthyridine in acetonitrile is considered to be due to the repulsion of two lone electron pairs on the two nitrogen atoms in 1,8-naphthyridine.
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