The zwitterion of 4-nitro-2-{(E)-[2-(piperidin-1-yl)ethyl]iminomethyl}phenol

被引：9
|
作者：
Santos-Contreras, Rocio J. [1 ]
Ramos-Organillo, Angel [1 ]
Garcia-Baez, Efren V. [2 ]
Padilla-Martinez, Itzia I. [2 ]
Martinez-Martinez, Francisco J. [1 ]
机构：
[1] Univ Colima, Fac Ciencias Quim, Coquimatlan Colima 28400, Mexico
[2] Inst Politecn Nacl, Unidad Profes Inter Disciplinaria Biotechnol, Mexico City 07340, DF, Mexico
来源：
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2009年 / 65卷
关键词：
HYDROGEN-BOND; AB-INITIO; H-BOND; PI; DERIVATIVES; ELECTRON; CRYSTAL;
D O I：
10.1107/S0108270108040407
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The title Schiff base compound, 4-nitro-1-oxo-2-{(E)-[2-(piperidin-1-yl)ethyl]iminiomethyl}cyclohexadienide, C14H19-N3O3, exists as a zwitterion, with the H atom of the phenol group being transferred to the imine N atom. The C=O, C-Ar-C-Ar and C-N bond lengths are in agreement with the oxocyclohexadienide-iminium zwitterionic form. The iminium H atom is engaged in a strong intramolecular hydrogen bond with the O atom of the keto group (N+-H center dot center dot center dot O) to form an S(6) motif. Soft C-H center dot center dot center dot O interactions in the ac plane lead to the development of hydrogen-bonded tapes, which are pi-stacked through the oxocyclohexadienide ring and iminium group. The significance of this study is in providing crystallographic evidence, supported by NMR and IR data, of the predominance of the oxocyclohexadienide-iminium zwitterion form over the noncharged canonical form in the title Schiff base.
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收藏
页码：O8 / O10
页数：3
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