Intramolecular hydrogen bonding and tautomerism in 1-[N-(4-bromophenyl)]aminomethylidene-2(1H) naphthalenone

被引：0
作者：
H. Ünver
D.M. Zengin
K. Güven
机构：
[1] Ankara University,Department of Physics, Faculty of Sciences
[2] Ankara University,Department of Physics, Faculty of Sciences
[3] University of Kirikkale,Department of Physics, Faculty of Art and Sciences
来源：
Journal of Chemical Crystallography | 2000年 / 30卷
关键词：
Bidentate Schiff base ligand; intramolecular hydrogen bond; photochromism; thermochromism; tautomerism;
D O I：
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中图分类号：
学科分类号：
摘要：
1-[N-(4-bromophenyl)]aminomethylidene-2(1H)naphthalenone (C17H12NOBr) (1) was synthesized and its crystal structure was determined. Compound (1) is monoclinic, space group P21/n with a = 4.808(1) Å, b = 20.617(1) Å, c = 13.750(1) Å, β = 93.004(1)°, V = 1361.11(3) Å3, Z = 4, Dc = 1.592 g·cm−3, μ(Mo Kα) = 3.014 mm−1, R = 0.051 for 1013 reflections [I > 2σ(I)]. There is a strong intramolecular hydrogen bond of distance 2.544(2) Å between the hydroxyl oxygen atom and imine nitrogen atom, the hydrogen atom essentially being bonded to the nitrogen atom. The title molecule is not planar. X-ray crystal structure determination reveals the existence of the keto (or predominantly keto) tautomer in (1). Spectra of compound (1) were observed by IR and NMR, and UV–visible spectra of (1) were studied in different solvents and acidic media.
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页码：359 / 364
页数：5
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