Through-resonance assisted ionic hydrogen bonding in 5-nitro-N-salicylideneethylamine

被引:118
作者
Krygowski, TM
Wozniak, K
Anulewicz, R
Pawlak, D
Kolodziejski, W
Grech, E
Szady, A
机构
[1] WARSAW UNIV,DEPT CHEM,PL-02093 WARSAW,POLAND
[2] MED ACAD WARSAW,DEPT INORGAN & ANALYT CHEM,PL-02097 WARSAW,POLAND
[3] TECH UNIV SZCZECIN,PL-71065 SZCZECIN,POLAND
关键词
D O I
10.1021/jp970814a
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
Structural and spectroscopic properties of hydrogen bonding in solid 5-nitro-N-salicylideneethylamine have been investigated. This is the first example of ionic [O-... H-N+] intramolecular hydrogen bonding in a structure of Schiff base. Single-crystal X-ray diffraction and C-13 magic-angle spinning NMR show that the title molecule is dominated by ionic canonical structures favored by through molecule conjugation between the nitro group and both groups of salicylidene fragment. Being involved in strong intramolecular [O-... H-N+] hydrogen bonding, 5-nitro-N-salicylideneethylamine forms its crystal lattice by means of different types of weak intermolecular [O-... H-N+], N-H ... O and C-H ... O hydrogen bonds. On the basis of the solid-state NMR results, it has been suggested that the acidic proton can also stay at the oxygen atom, and this is qualitatively supported by X-ray diffraction.
引用
收藏
页码:9399 / 9404
页数:6
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