Anisotropic and hydrogen bonding effects in phenylglyoxamides and mandelamides: theoretical and NMR conformational evaluation

被引：4

作者：

Goncalves, Biank T. ^{[1
]}

Esteves, Pierre M. ^{[1
]}

Pinto, Angelo C. ^{[1
]}

Kaiser, Carlos R. ^{[1
]}

da Silva, Fernanda L. ^{[1
]}

Miguez, Eduardo ^{[2
]}

da Silvaa, Joaquirn F. M. ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Dept Quim Organ, Inst Quim, BR-21949900 Rio De Janeiro, RJ, Brazil

[2] Univ Fed Rio de Janeiro, Inst Macromol Profa Eloisa Mano, BR-21945970 Rio De Janeiro, RJ, Brazil

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 2008年 / 46卷 / 05期

关键词：

NMR; PM3; calculations; DFT calculations; anisotropic effects; hydrogen bonding; H-1; C-13; phenylglyoxamides; mandelamides;

D O I：

10.1002/mrc.2192

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

interesting anisotropic effects were observed for phenylglyoxamides and their respective mandelamides. Such effects were observed in experimental H-1 and C-13 NMR (in CDCl3, CD3OD, and DMSO-d(6) solvents) and in some cases with good correlation to theoretical H-1 and C-13 NMR DFT-GIAO (B3LYP/6-311++G**//B3LYP/6-31G*) calculations. A systematic conformational analysis of these compounds was performed in a two-step methodology, using PM3 and DFT (B3LYP/6-31G*) calculations; with good accomplishment and computational time economy. It was observed that intramolecular hydrogen bonding plays a significant role in the conformation of such compounds. Finally, a geminal nonequivalence of an N-C (H) under bar (2) moiety, in one of the alkyl side chain (R1=R2), was found for the tertiary mandelamides studied. Copyright (C) 2008 John Wiley & Sons, Ltd.

引用

页码：418 / 426

页数：9

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