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Synthesis and characterization of a novel functionalized magnetic Fe 3 O 4 as a nanocatalyst for synthesis and antibacterial activities of 2-amino-3-phenylsulfonyl-4-aryl-4H-benzo[h]chromens derivatives and theoretical study on the mechanism using a DFT Method
Research on Chemical Intermediates ( IF 3.3 ) Pub Date : 2020-01-27 , DOI: 10.1007/s11164-020-04094-y
Arezoo Mazaheri , Mehdi Bostanian

Abstract

In this work, a new organic–inorganic hybrid heterogeneous and efficient magnetic nanocatalyst was fabricated with 4-aminopyridine (AP)-functionalized Fe3O4 (Fe3O4@AP) nanoparticles. Then, prepared nanocatalyst was characterized by FT-IR, XRD, TGA, TEM and SEM techniques. The catalytic activity of the magnetic nanocatalyst was employed to synthesis of 2-amino-3-phenylsulfonyl-4-aryl-4H-benzo[h]chromens derivatives through one-pot three-component reactions of α-naphtol with aromatic aldehyde and (phenylsulfonyl) acetonitrile under ethanol solvent at 60 °C conditions. The synthetic compounds exert moderate activity against both Gram-positive and Gram-negative bacteria and their effectiveness is higher against Bacillus subtilis. This green nanocatalytic procedure has advantages such as excellent recoverability, short reaction time, simple and comfortable procedure, ready separation with an external magnet with no considerable loss of its catalytic efficiency, high yields and biocompatibility. The mechanism of the reaction investigated by density functional theory-based modelling is also reported. Results of this study show that the reaction has four TS structure. For TS1, mode using GaussView software clearly shows the animation of the imaginary frequency with a vibration frequency at − 874.23 cm−1 and TS2 at − 1058.67 cm−1. Also, the transition state for TS3 and TS4 shows an imaginary frequency with a vibration frequency at − 1044.65 cm−1 and at − 815.11 cm−1. This study aims at giving insight into the mechanism of the 2-amino-3-phenylsulfonyl-4-aryl-4H-benzo[h]chromens reaction in the presence of nanocatalyst of Fe3O4@AP.

Graphic abstract



中文翻译:

新型功能化磁性Fe 3 O 4的合成,表征,纳米催化剂用于2-氨基-3-苯基磺酰基-4-芳基-4H-苯并[h]铬原子衍生物的合成和抗菌活性以及DFT机理的理论研究方法

摘要

在这项工作中,使用4-氨基吡啶(AP)-官能化的Fe 3 O 4(Fe 3 O 4)制备了一种新型的有机-无机杂化杂化高效磁性纳米催化剂。@AP)纳米粒子。然后,通过FT-IR,XRD,TGA,TEM和SEM技术对制备的纳米催化剂进行了表征。利用磁性纳米催化剂的催化活性,通过α-萘酚与芳族醛和(苯磺酰基)的一锅三组分反应,合成了2-氨基-3-苯基磺酰基-4-芳基-4H-苯并[h]铬原子衍生物乙腈在60°C条件下的乙醇溶剂中。合成化合物对革兰氏阳性菌和革兰氏阴性菌均具有中等活性,并且对枯草芽孢杆菌的有效性更高。这种绿色的纳米催化方法具有以下优点:可回收性好,反应时间短,操作简单舒适,可与外部磁体轻松分离,而催化效率却没有显着降低,产率和生物相容性高。还报道了通过基于密度泛函理论的模型研究的反应机理。研究结果表明,该反应具有四个TS结构。对于TS1,使用GaussView软件的模式可以清楚地显示虚频率的动画,振动频率为− 874.23 cm-1和TS2在− 1058.67 cm -1处。另外,TS3和TS4的过渡状态示出了具有在-1044.65cm -1和在-815.11cm -1处的振动频率的假想频率。这项研究旨在深入了解在Fe 3 O 4 @AP纳米催化剂存在下2-氨基-3-苯基磺酰基-4-芳基-4H-苯并[h]铬原子反应的机理。

图形摘要

更新日期:2020-03-16
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