{"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}
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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.
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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.
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