Reaction of N-Allenyl-1H-Pyrrole-2-Yl-Carbaldehydes With Hydroxylamine: A Quantum Chemical Insight Into the Mechanism and Substituent Influence

IF 1.9 4区化学 Q2 CHEMISTRY, ORGANIC

Journal of Physical Organic Chemistry Pub Date : 2025-06-01 DOI:10.1002/poc.70023

Alexander S. Bobkov, Nikita V. Teplyashin, Svetlana V. Martynovskaya, Andrey V. Ivanov, Nadezhda M. Vitkovskaya

引用次数: 0

Abstract

We report on a quantum chemical study (B2PLYP-D3BJ/6-311+G**//B3LYP/6-31+G*) of the mechanism of the reaction of N-allenyl-1H-pyrrole-2-yl-carbaldehydes with hydroxylamine in ethanol leading to pyrrolopyrazine oxides. The main focus is placed on unraveling the influence of the nature of the substituent in the fourth and fifth positions of the pyrrole ring on the kinetic characteristics of the key stages of the reaction, which are oximation and intramolecular cyclization. The aryl substituents are found to favor the reaction, in contrast to the alkyl substituents.

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n -烯基- 1h -吡咯-2-酰基-乙醛与羟胺的反应：机理和取代基影响的量子化学见解

本文报道了n -烯基- 1h -吡咯-2-基-乙醛在乙醇中与羟胺反应生成吡咯吡嗪氧化物的量子化学研究（B2PLYP-D3BJ/6-311+G**//B3LYP/6-31+G*）。本研究的重点是揭示吡咯环第4位和第5位取代基的性质对反应关键阶段（模拟和分子内环化）动力学特征的影响。与烷基取代基相比，芳基取代基更有利于反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Physical Organic Chemistry 化学-物理化学

CiteScore

3.60

自引率

11.10%

发文量

161

审稿时长

2.3 months

期刊介绍： The Journal of Physical Organic Chemistry is the foremost international journal devoted to the relationship between molecular structure and chemical reactivity in organic systems. It publishes Research Articles, Reviews and Mini Reviews based on research striving to understand the principles governing chemical structures in relation to activity and transformation with physical and mathematical rigor, using results derived from experimental and computational methods. Physical Organic Chemistry is a central and fundamental field with multiple applications in fields such as molecular recognition, supramolecular chemistry, catalysis, photochemistry, biological and material sciences, nanotechnology and surface science.