A kinetic study of the mechanism of esterification of 1-arylethanols in trifluoroacetic acid |
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Authors: | Ciaran J Gillen Anthony C Knipe William E Watts |
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Institution: | School of Physical Sciences, New University of Ulster, Coleraine, Northern Ireland BT52 ISA, U.K. |
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Abstract: | Aryl substituent effects upon the rate constants for the esterification of a series of 1-arylethanols in trifluoroacetic acid are in accordance with a reverse AAL1 mechanism, for which the Hammett reaction constant ? = ?3.69 has been determined by correlation with σ+ substituent constants. The rates of reaction are ca. 50-fold faster than those for corresponding benzyl alcohols which bear an electron-donating aryl substituent and which are also believed to undergo esterification in trifluoroacetic acid by the reverse AAL1 mechanism; the reverse AAC2 mechanism applies to benzyl alcohols which bear an electron- withdrawing aryl substituent. |
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