A Study on the Kinetics and Mechanism of the One-Pot Formation of 3,4,5-Substituted Furan-2(5H)-Ones in the Presence of Lactic Acid: Effect of Different Substituents

IF 2.1 4区化学 Q3 CHEMISTRY, PHYSICAL

Progress in Reaction Kinetics and Mechanism Pub Date : 2018-10-01 DOI:10.3184/146867818X15319903829218

Osman Asheri, S. Habibi‐Khorassani, M. Shahraki

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引用次数: 3

Abstract

The kinetics of the reaction between para-substituted anilines and dimethyl acetylenedicarboxylate (DMAD) with derivatives of benzaldehyde for the one-pot formation of 3,4,5-substituted furan-2(5H)-ones in the presence of lactic acid as a catalyst have been studied spectrophotometrically at different temperatures. A mechanism involving four steps was proposed for the reactions, all of which followed second-order kinetics. The partial orders with respect to substituted aniline and DMAD were one and one and the reactions revealed zero-order kinetics for benzaldehyde and its derivatives. Changing of substituents on benzaldehyde left rates of reaction unaffected. However, various substituents on aniline showed that para electron-withdrawing groups decreased the rate of reaction. According to investigation of an isokinetic relationship, a common mechanism exists for all studied substituents and a general mechanism can be formulated. Kinetic values (k and Ea) and associated activation parameters (ΔG‡, ΔS‡ and ΔH‡) of the reactions were determined.

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乳酸存在下一锅生成3,4,5-取代呋喃-2(5H)- 1的动力学及机理研究:不同取代基的影响

用分光光度法研究了在不同温度下对取代苯胺与苯甲醛衍生物二甲基乙炔二羧酸酯(DMAD)在乳酸催化下一锅反应生成3,4,5-取代呋喃-2(5H)-酮的动力学。提出了一个包含四个步骤的反应机理，所有反应都遵循二级动力学。取代苯胺和DMAD的偏序分别为一阶和一阶，苯甲醛及其衍生物的反应表现为零级动力学。改变苯甲醛上的取代基不影响反应速率。然而，苯胺上的各种取代基表明，对吸电子基团降低了反应速率。根据对等动力学关系的研究，所研究的取代基存在一个共同的反应机理，并可形成一个通用的反应机理。测定了反应的动力学值(k和Ea)和相关的活化参数(ΔG‡，ΔS‡和ΔH‡)。

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来源期刊

Progress in Reaction Kinetics and Mechanism 化学-物理化学

CiteScore

2.10

自引率

0.00%

发文量

审稿时长

2.3 months

期刊介绍： The journal covers the fields of kinetics and mechanisms of chemical processes in the gas phase and solution of both simple and complex systems.