Kinetic study of the esterification of arylmethanols in trifluoroacetic acid: mechanistic change consequent upon aryl substituent effects

Kinetic study of the esterification of arylmethanols in trifluoroacetic acid: mechanistic change consequent upon aryl substituent effects
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DOI:
10.1039/c39790000905
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发表时间:
1979
期刊:
Journal of The Chemical Society, Chemical Communications
影响因子:
--
通讯作者:
P. Kavanagh;A. C. Knipe;W. Watts
P. Kavanagh;A. C. Knipe;W. Watts
中科院分区:
其他
文献类型:
--
作者:
P. Kavanagh;A. C. Knipe;W. Watts

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对于带有吸电子取代基 (ρ=–0·79) 的底物,芳基取代基对一系列芳基甲醇在纯三氟乙酸中酯化的速率常数的影响符合反向 AAC2 机制,而对于带有甲基取代基的底物则表明反向 AAL1 机制。
Aryl substituent effects upon the rate constants for the esterification of a series of arylmethanols in neat trifluoroacetic acid are in accordance with a reverse AAC2 mechanism for those substrates bearing an electron-withdrawing substituent (ρ=–0·79), whereas a reverse AAL1 mechanism is indicated for those bearing a methyl substituent.