N-Boron-pyrrole: A negative charge stabilizing group

IF 3 3区 化学 Q3 CHEMISTRY, PHYSICAL Computational and Theoretical Chemistry Pub Date : 2024-11-26 DOI:10.1016/j.comptc.2024.115000
Younes Valadbeigi
{"title":"N-Boron-pyrrole: A negative charge stabilizing group","authors":"Younes Valadbeigi","doi":"10.1016/j.comptc.2024.115000","DOIUrl":null,"url":null,"abstract":"<div><div>We show that the N-boron-pyrrole (B-pyrrole) group stabilizes the negatively charged compounds, despite not being an electron withdrawing group (EWG). Density functional theory (DFT) calculations revealed that this distinctive property of the B-pyrrole group arises from enhanced π-electron delocalization within the pyrrole ring. The effect of B-pyrrole group on the Brønsted and Lewis acidity of various compound classes was examined and compared with common EWGs including F, Cl, Br, CN, NO<sub>2</sub>. Substitution of pyrrole into the boracyclohexadiene derivatives enhances their acidity by about 1–6 kcal mol<sup>−1</sup> while the acidity enhancement due to pyrrole substitution into boric acid was about 17 kcal mol<sup>−1</sup>. Interestingly, B(Pyrrole)<sub>3</sub> exhibited a fluoride affinity comparable to BF<sub>3</sub> (∼78 kcal mol<sup>−1</sup>) and approximately 15 kcal mol<sup>−1</sup> higher than that of BH<sub>3</sub>.</div></div>","PeriodicalId":284,"journal":{"name":"Computational and Theoretical Chemistry","volume":"1243 ","pages":"Article 115000"},"PeriodicalIF":3.0000,"publicationDate":"2024-11-26","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/S2210271X24005395","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

We show that the N-boron-pyrrole (B-pyrrole) group stabilizes the negatively charged compounds, despite not being an electron withdrawing group (EWG). Density functional theory (DFT) calculations revealed that this distinctive property of the B-pyrrole group arises from enhanced π-electron delocalization within the pyrrole ring. The effect of B-pyrrole group on the Brønsted and Lewis acidity of various compound classes was examined and compared with common EWGs including F, Cl, Br, CN, NO2. Substitution of pyrrole into the boracyclohexadiene derivatives enhances their acidity by about 1–6 kcal mol−1 while the acidity enhancement due to pyrrole substitution into boric acid was about 17 kcal mol−1. Interestingly, B(Pyrrole)3 exhibited a fluoride affinity comparable to BF3 (∼78 kcal mol−1) and approximately 15 kcal mol−1 higher than that of BH3.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
n-硼吡咯:一种负电荷稳定基团
我们发现n-硼吡咯(b -吡咯)基团稳定带负电荷的化合物,尽管不是一个吸电子基团(EWG)。密度泛函理论(DFT)计算表明,b -吡咯基团的这种特殊性质是由吡咯环内π电子离域增强引起的。考察了b -吡咯基团对各类化合物Brønsted和Lewis酸度的影响,并与F、Cl、Br、CN、NO2等常见ewg进行了比较。吡咯取代硼环己二烯衍生物使其酸度提高约1 - 6 kcal mol−1,而吡咯取代硼酸使其酸度提高约17 kcal mol−1。有趣的是,B(Pyrrole)3具有与BF3相当的氟亲和性(约78 kcal mol - 1),比BH3高约15 kcal mol - 1。
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 去求助
来源期刊
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.
期刊最新文献
Editorial Board Topological analysis of metal–organic frameworks: A regression approach to enhance molecular modeling Mechanistic insights into the interaction of NO, char‑nitrogen and NH3 during ammonia-coal combustion Theoretical investigation on the alcoholysis reaction mechanism of nerve agents: The reaction of tabun with methanol Molecular design and theoretical investigation on novel (D)2-π-a photosensitizers based on coumarin dye: Impact of boron dipyrromethene bridge on UV–vis and optoelectronic properties
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1