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
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
收藏
页码:8104 / 8111
页数:8
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