Acidity effect on the cleavage of ether function intramolecularly assisted by the amide group. Part 5

被引：7

作者：

Arcelli, A ^{[1
]}

Cecchi, R ^{[1
]}

Porzi, G ^{[1
]}

Rinaldi, S ^{[1
]}

Sandri, S ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 31期

关键词：

amides; cleavage reactions; ethers; kinetics; neighbouring group effect;

D O I：

10.1016/S0040-4020(01)00638-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rate dependence on both the acidity and the temperature of the hydrolysis of N-(methoxyprop-2-yl)benzanilide (1), assisted by vicinal amide function, was investigated and the thermodynamic activation parameters were calculated. The rate constant of the first ste of the overall process increases when the acidity is raised, while the second step is slowed down. The negative value of DeltaS(not equal) (-100.9 J mol(-1) K-1) measured for the second step suggests the participation of water in the transition state. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6843 / 6846

页数：4

共 14 条

[1] KINETICS OF SERIES FIRST-ORDER REACTIONS - ANALYSIS OF SPECTROPHOTOMETRIC DATA BY METHOD OF LEAST SQUARES AND AN AMBIGUITY [J].