The prototropic tautomerism and substituent effect through strong electron-withdrawing group in (E)-5-(diethylamino)-2-[(3-nitrophenylimino)methyl]phenol

被引：22

作者：

Albayrak, Cigdem ^{[1
]}

Kastas, Gokhan ^{[1
]}

Odabasoglu, Mustafa ^{[2
]}

Frank, Rene ^{[3
]}

机构：

[1] Sinop Univ, Fac Educ, TR-57000 Sinop, Turkey

[2] Pamukkale Univ, Chem Technol Program, TR-20070 Kinikli Denizli, Turkey

[3] Univ Leipzig, Fac Chem & Mineral, D-04103 Leipzig, Germany

来源：

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY | 2013年 / 114卷

关键词：

Schiff base; DFT; Computational study; Intramolecular proton transfer; FT-IR; UV-vis; MACROCYCLIC LIGAND DESIGN; DENSITY-FUNCTIONAL THEORY; SCHIFF-BASE LIGANDS; HYDROGEN-BOND; EXCITATION-ENERGIES; CRYSTAL-STRUCTURE; SOLID-STATE; COMPLEXES; COPPER(II); NICKEL(II);

D O I：

10.1016/j.saa.2013.05.044

中图分类号：

O433 [光谱学];

学科分类号：

0703 ; 070302 ;

摘要：

The prototropic tautomerism in o-Hydroxy Schiff bases results in two forms called phenol-imine and keto-amine. The preference of a particular form by the compound changes in the solid and solvent media. The choice can also be regulated by a substituent with a different electron-donating or withdrawing group. In the present study, the above-mentioned factors are considered in the investigation of (E)-5-(diethylamino)-2-[(3-nitrophenylimino)methyl]phenol compound (an o-Hydroxy Schiff basis) by experimental (XRD, FT-IR and UV-vis) and computational (DFT and TD-DFT) methods. The results show that the title compound adopts only phenol-imine form in the solid and solvent media. This was attributed to the substituent effect through strong electron-withdrawing nitro group. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：205 / 213

页数：9

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