Quantum-Chemical Study of Keto–Enol Equilibrium and Global Electrophilicity of Hydroxymaleimide Derivatives

IF 1.1 4区化学 Q4 CHEMISTRY, PHYSICAL

Doklady Physical Chemistry Pub Date : 2023-05-24 DOI:10.1134/S001250162360002X

A. A. Panov

引用次数: 0

Abstract

The energies of enol and keto forms for 36 3-hydroxymaleimide derivatives have been calculated by the DFT and DLPNO methods. The results clearly show that, with only a few exceptions, the enol form is energetically more favorable by 16–60 kJ mol^–1, and the energy difference depends on the substituent in the 4-position. Global electrophilic index has been calculated for all the compounds, which demonstrates that the keto form is generally more electrophilic, and electrophilicity depends on the substituent in the 4-position. Two possible structures of hydroxymaleimide anion have been evaluated; the deprotonation of the oxygen atom turns out to be the most energetically favorable.

Abstract Image

查看原文本刊更多论文

酮烯醇平衡和羟基马来酰亚胺衍生物整体亲电性的量子化学研究

用DFT和DLPNO方法计算了36个3-羟基马来酰亚胺衍生物的烯醇和酮的能量。结果清楚地表明，除了少数例外，烯醇形式在能量上更有利16-60 kJ mol-1，并且能量差取决于4位取代基。计算了所有化合物的整体亲电性指数，表明酮型化合物一般更亲电，亲电性取决于4位取代基。对羟基马来酰亚胺阴离子的两种可能结构进行了评价;氧原子的去质子化是能量上最有利的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Doklady Physical Chemistry 化学-物理化学

CiteScore

1.50

自引率

0.00%

发文量

审稿时长

6-12 weeks

期刊介绍： Doklady Physical Chemistry is a monthly journal containing English translations of current Russian research in physical chemistry from the Physical Chemistry sections of the Doklady Akademii Nauk (Proceedings of the Russian Academy of Sciences). The journal publishes the most significant new research in physical chemistry being done in Russia, thus ensuring its scientific priority. Doklady Physical Chemistry presents short preliminary accounts of the application of the state-of-the-art physical chemistry ideas and methods to the study of organic and inorganic compounds and macromolecules; polymeric, inorganic and composite materials as well as corresponding processes. The journal is intended for scientists in all fields of chemistry and in interdisciplinary sciences.