A first principle study of Nitrogen/Carbon replacement in a set of β-aminoacrolein/β-thioaminoacrolein derivatives

IF 3 3区化学 Q3 CHEMISTRY, PHYSICAL

Computational and Theoretical Chemistry Pub Date : 2025-02-01 DOI:10.1016/j.comptc.2024.115053

Malihe Shahraki, Alireza Nowroozi, Ebrahim Nakhaei

{"title":"A first principle study of Nitrogen/Carbon replacement in a set of β-aminoacrolein/β-thioaminoacrolein derivatives","authors":"Malihe Shahraki, Alireza Nowroozi, Ebrahim Nakhaei","doi":"10.1016/j.comptc.2024.115053","DOIUrl":null,"url":null,"abstract":"<div><div>This study systematically investigates the impact of N/C substitution in β-aminoacrolein/β-thioaminoacrolein derivatives at various theoretical levels. Key electronic energy components, including electron configuration, nitrogen atom positioning, lone pair-lone pair (Lp-Lp) repulsion, and resonance-assisted hydrogen bonding (RAHB), are evaluated. Results reveal that electron configuration contributes the most stabilizing energy (∼-16 Hartree), while nitrogen positioning and Lp-Lp repulsions destabilizes structures, following the trend: N2 < N1 < N3. RAHB energies are strongly influenced by nitrogen count, with stability improving in the order: N1 (−0.0145) < N2 (−0.0273) < N3 (−0.0370) < N1N2 (−0.0418) < N1N3 (−0.0515) < N2N3 (−0.0643) < N1N2N3 (-0.0788H). Furthermore, energetic, structural, spectral, and topological descriptors support these findings. Interestingly, the aromaticity index indicates a slight reduction in π-electron delocalization (π-ED) with N/C substitution, challenging conventional RAHB theory.</div></div>","PeriodicalId":284,"journal":{"name":"Computational and Theoretical Chemistry","volume":"1244 ","pages":"Article 115053"},"PeriodicalIF":3.0000,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Computational and Theoretical Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2210271X24005929","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

Abstract

This study systematically investigates the impact of N/C substitution in β-aminoacrolein/β-thioaminoacrolein derivatives at various theoretical levels. Key electronic energy components, including electron configuration, nitrogen atom positioning, lone pair-lone pair (Lp-Lp) repulsion, and resonance-assisted hydrogen bonding (RAHB), are evaluated. Results reveal that electron configuration contributes the most stabilizing energy (∼-16 Hartree), while nitrogen positioning and Lp-Lp repulsions destabilizes structures, following the trend: N2 < N1 < N3. RAHB energies are strongly influenced by nitrogen count, with stability improving in the order: N1 (−0.0145) < N2 (−0.0273) < N3 (−0.0370) < N1N2 (−0.0418) < N1N3 (−0.0515) < N2N3 (−0.0643) < N1N2N3 (-0.0788H). Furthermore, energetic, structural, spectral, and topological descriptors support these findings. Interestingly, the aromaticity index indicates a slight reduction in π-electron delocalization (π-ED) with N/C substitution, challenging conventional RAHB theory.

Abstract Image

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

来源期刊

Computational and Theoretical Chemistry CHEMISTRY, PHYSICAL-

CiteScore

4.20

自引率

10.70%

发文量

331

审稿时长

31 days

期刊介绍： Computational and Theoretical Chemistry publishes high quality, original reports of significance in computational and theoretical chemistry including those that deal with problems of structure, properties, energetics, weak interactions, reaction mechanisms, catalysis, and reaction rates involving atoms, molecules, clusters, surfaces, and bulk matter.