Structure and tautomerism of 4-bromo substituted 1H-pyrazoles

被引：37

作者：

Trofimenko, Swiatoslav ^{[2
]}

Yap, Glenn P. A. ^{[2
]}

Jove, Fernando A. ^{[2
]}

Claramunt, Rosa M. ^{[1
]}

Garcia, M. Angeles ^{[1
]}

Maria, M. Dolores Santa ^{[1
]}

Alkorta, Ibon ^{[3
]}

Elguero, Jose ^{[3
]}

机构：

[1] Univ Nacl Educ Distancia, Fac Ciencias, Dept Quim Organ & Bioorgan, E-28050 Madrid, Spain

[2] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

[3] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

TETRAHEDRON | 2007年 / 63卷 / 34期

关键词：

bromopyrazoles; tautomerism : X-ray structure; solid-state NMR; DFT calculations; GIAO calculations;

D O I：

10.1016/j.tet.2007.06.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tautomerism in the solid state and in solution of five 4-bromo-1H-pyrazoles has been studied by multinuclear magnetic resonance spectroscopy and, for one of them, by X-ray crystallography (3,4-dibromo-5-phenyl-1H-pyrazole). When there is a bromine atom at position 3(5), in all cases, the tautomer present in the solid state is the 3-bromo one. In solution, the same tautomer is the major one. DFT calculations justify the predominance of 3-bromo tautomers over 5-bromo ones and provide some useful chemical shifts obtained through GIAO calculations. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8104 / 8111

页数：8

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