Synthesis, characterization and spectroscopic investigation of N-(2-acetylbenzofuran-3-yl)acrylamide monomer: Molecular structure, HOMO-LUMO study, TD-DFT and MEP analysis

被引：84

作者：

Barim, E. ^{[1
]}

Akman, F. ^{[2
]}

机构：

[1] Univ Munzur, Vocat Sch Tunceli, TR-62000 Tunceli, Turkey

[2] Univ Bingol, Vocat Sch Tech Sci, TR-12000 Bingol, Turkey

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2019年 / 1195卷

关键词：

Benzofuran; Acrylamide; DFT; HOMO-LUMO; MEP; DENSITY-FUNCTIONAL THEORY; BENZOFURAN DERIVATIVES; INHIBITORS; ACRYLAMIDE;

D O I：

10.1016/j.molstruc.2019.06.015

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：

In this study, a novel acrylamide monomer was synthesized and characterized by UV-Vis, FT-IR and H-1 NMR measurements. The acrylamide monomer namely, N-(2-acetyl-benzofuran-3-yl)acrylamide (NABA), was prepared in two steps. In the first step, 1-(3-aminobenzofuran-2-yl)ethan-1 -one was synthesized by the reaction of 1-chloroacetone with 2-hydroxy-benzonitrile under basic conditions. In the second step, the obtained 1-(3-aminobenzofuran-2-yl)ethan-1 -one was reacted with acryloyl chloride and triethylamine at 0-5 degrees C temperature for obtaining NABA monomer. Then, the structural, vibrational, nuclear magnetic resonance and electronic properties for the synthesized monomer were determined by quantum chemical calculations of DFT method. The results were compared with experimental FT-IR, H-1 NMR and UV-Vis spectral data. The band gap of HOMO and LUMO show that the NABA monomer is chemically active and has charge transfer within the monomer. Moreover, molecular electrostatic potential (MEP) maps were drawn to identify reactive regions of NABA monomer. (C) 2019 Elsevier B.V. All rights reserved.

引用

页码：506 / 513

页数：8

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