Intramolecular dihydrogen bond A new perspective in Lewis acid catalyzed nucleophilic epoxide ring opening reaction

被引：3

作者：

Dixit, Vaibhav A. ^{[1
]}

Rathi, Prakash C. ^{[1
]}

Bharatam, Prasad V. ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Mohali 160062, Punjab, India

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2010年 / 962卷 / 1-3期

关键词：

Dihydrogen bond; Epoxide ring opening; Frustrated Lewis pairs; Hydrogen elimination; Storage; UNCONVENTIONAL HYDROGEN-BONDS; DENSITY-FUNCTIONAL THEORY; ETHYLENE-OXIDE; AB-INITIO; REARRANGEMENT; COMPLEXES; MECHANISM;

D O I：

10.1016/j.theochem.2010.09.020

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Nucleophilic epoxide ring opening reactions can be effectively carried out with BF3 but not with BH3 This has been traced to the formation of an intermediate with an intramolecular dihydrogen bond which prefers to yield a species with frustrated Lewis acid-base pair after liberating H-2 molecule in the BH3 catalyzed system Quantum chemical analysis indicates that the H-2 liberation is more favorable by 37 8 kcal/mol in comparison to the desired aminoalcohol formation (C) 2010 Elsevier B V All rights reserved

引用

页码：97 / 100

页数：4

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