General method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones (X = ferrocenyl, OMe, Me, I, Cl, and NO2) from 2-methoxy-1,4-naphthoquinone and investigation of H+ and Mg2+ catalysts with DFT calculations

被引：26

作者：

Francisco, Acacio I. ^{[1
]}

Vargas, Maria D. ^{[1
]}

Carneiro, J. Walkimar de M. ^{[1
]}

Lanznaster, Mauricio ^{[1
]}

Torres, Jose C. ^{[3
]}

Camara, Celso A. ^{[2
]}

Pinto, Angelo C. ^{[4
]}

机构：

[1] Univ Fed Fluminense, Inst Quim, BR-24020141 Niteroi, RJ, Brazil

[2] Univ Fed Rural Pernambuco, Inst Quim, Recife, PE, Brazil

[3] CEFET Quim, Unidade Nilopolis, BR-26530060 Nilopolis, RJ, Brazil

[4] Univ Fed Rio de Janeiro, Inst Quim, BR-21949900 Rio De Janeiro, Brazil

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2008年 / 891卷 / 1-3期

关键词：

1,4-Naphthoquinone; Ferrocenylphenyleneamine-1,4-naphthoquinone; Nucleophilic substitution; DFT calculations; UV-vis spectra;

D O I：

10.1016/j.molstruc.2008.03.028

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：

A rapid and simple method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones from 2 -methoxy-1,4-naphthoquinone, in boiling MeOH, using MgCl2 and p-toluenesulfonic acid as catalysts is described. This methodology has been applied successfully to the synthesis of electron donor (4-OMe, 4-Me, 4-ferrocenyl) and electron withdrawing (4-1,4-Cl, 4- and 3-NO2) aniline derivatives. The effect of both H+ and Mg2+ as catalysts was investigated using DFT calculations carried out at the B3LYP/6-31G(d) level. The electronic properties of the novel 2-(4-ferrocenylphenylene)amine-1,4-naphthoquinone 3b were investigated and show that the ferrocenyl and the methoxy group have similar electron donor properties in 2-(4-methoxy)amine-1,4-naphthoquinone 3a. (C) 2008 Elsevier B.V. All rights reserved.

引用

页码：228 / 232

页数：5

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