Study of the decarboxylation mechanism of fluorobenzoic acids by strong N-bases

被引：20

作者：

Gierczyk, B

Wojciechowski, G

Brzezinski, B

Grech, E

Schroeder, G

机构：

[1] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland

[2] Tech Univ Szczecin, Inst Chem & Environm Protect, PL-71065 Szczecin, Poland

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2001年 / 14卷 / 10期

关键词：

pentafluorobenzoic acid; tetrafluorobenzoic acid; N-bases; kinetics; decarboxylation; F-19; NMR; Fourier transform infrared;

D O I：

10.1002/poc.419

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The kinetics of the decarboxylation reactions of pentafluorobenzoic and tetrafluorobenzoic acids by various N-bases were studied using F-19 NMR spectroscopy. The rate constants of these reactions are dependent on the structure of the fluorinated acid and the pK(a) values of the N-bases. Pentafluorobenzoic acid is decarboxylated about two orders of magnitude faster than tetrafluorobenzoic acid. With increasing pK(a) values of the protonated N-bases these reactions became much slower. These results suggested that the rate-determining step of the studied reactions is the attack of the conjugated acid (protonated N-base) on carboxylate anion. Copyright (C) 2001 John Wiley & Sons, Ltd.

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页码：691 / 696

页数：6

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