The C-F bond as a tool in the conformational control of amides

被引：82

作者：

Briggs, CRS

O'Hagan, D ^{[1
]}

Howard, JAK

Yufit, DS

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland

[3] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2003年 / 119卷 / 01期

关键词：

bond; amide; conformation;

D O I：

10.1016/S0022-1139(02)00243-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学]; 081704 [应用化学];

摘要：

The conformation of 2-fluoro-N-(2-fluoroethyl)-propionamide 4 in the solid state indicates the influence of both a P-fluorine-amide gauche effect and an alpha-fluoroamide effect. The structure reveals the influence of two recently observed stereoelectronic effects associated with the C-F bond, which has resulted in the successful prediction of the solid state conformation of amide 4. A gauche relationship (-69.9degrees) was observed for atoms N(1)-C(4)-C(5)-F and a syn planar (2.0degrees) relationship was observed for N(1)-C(3)-C(2)-F. The paper demonstrates the predictive power of using the C-F bond as a tool in influencing the conformation of amides and peptides. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：9 / 13

页数：5

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