New deuterium isotope effects on 13C and 19F chemical shifts across intramolecular hydrogen bonds of non-resonance assisted systems

被引：5
作者：
Sosnicki, JG
Hansen, PE
机构：
[1] Tech Univ Szczecin, Inst Chem & Environm Protect, PL-71065 Szczecin, Poland
[2] Roskilde Univ, Dept Life Sci & Chem, DK-4000 Roskilde, Denmark
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 05期
关键词：
hydrogen bond; isotope effect; C-13; NMR; F-19; thioanilides; anilides;
D O I：
10.1016/j.tetlet.2004.11.155
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of thioanilides and corresponding anilides, some of which contain fluorinated phenyl rings, have been synthesized as model compounds. They all contain rather strong intramolecular hydrogen bonds. the strength of which varies. Deuterium isotope effects on F-19 and C-13 chemical shifts due to deuteriation at the NH proton show interesting new long-range isotope effects on chemical shifts that may be related to the existence of an intramolecular hydrogen bond and to transmission of the isotope effect due to all electric field effect. Deuterium isotope effects on chemical shifts report oil variations in hydrogen bonding. for example, as a function of changes in substituents or temperature. Deuteriation leads to a strengthening of the hydrogen bond. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：839 / 842
页数：4
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