A theoretical view on the stereochemistry of 1,3-benzoxazol-2-(3H)-ylidenes obtained from double vinylic substitution.

IF 1.1 4区综合性期刊 Q3 MULTIDISCIPLINARY SCIENCES

Anais da Academia Brasileira de Ciencias Pub Date : 2024-08-23 eCollection Date: 2024-01-01 DOI:10.1590/0001-3765202420240156

Matheus P DE Freitas, Ana Júlia F Souza, Julliane Yoneda, Diego P Sangi

引用次数: 0

Abstract

2-(1,3-Benzoxazol-2(3H)-ylidene)-3-oxo-3-phenylpropanenitrile (1) and methyl-2-(1,3-benzoxazol-2(3H)-ylidene)(cyano)acetate (2) are observed as single isomers by NMR spectroscopy. A theoretical study was carried out to investigate if this is due to the exclusive presence of the most stable diastereoisomer or if the ene moiety undergoes fast rotation, thereby allowing for the observation of an average conformer. Indeed, the pronounced stabilization of the E stereoisomer, attributed to intramolecular hydrogen bonding, makes it the single obtained product.

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通过双乙烯基取代获得的 1,3-苯并恶唑-2-(3H)-亚基的立体化学理论观点。

通过核磁共振光谱观察到 2-(1,3-苯并恶唑-2(3H)-亚基)-3-氧代-3-苯基丙腈（1）和 2-(1,3-苯并恶唑-2(3H)-亚基)(氰基)乙酸甲酯（2）为单一异构体。我们进行了一项理论研究，以探讨这是由于只存在最稳定的非对映异构体，还是由于烯分子发生了快速旋转，从而观察到了平均构象。事实上，由于分子内氢键的作用，E 立体异构体具有明显的稳定性，使其成为唯一获得的产物。

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

Anais da Academia Brasileira de Ciencias 综合性期刊-综合性期刊

CiteScore

2.20

自引率

0.00%

发文量

347

审稿时长

1 months

期刊介绍： The Brazilian Academy of Sciences (BAS) publishes its journal, Annals of the Brazilian Academy of Sciences (AABC, in its Brazilianportuguese acronym ), every 3 months, being the oldest journal in Brazil with conkinuous distribukion, daking back to 1929. This scienkihic journal aims to publish the advances in scienkihic research from both Brazilian and foreigner scienkists, who work in the main research centers in the whole world, always looking for excellence. Essenkially a mulkidisciplinary journal, the AABC cover, with both reviews and original researches, the diverse areas represented in the Academy, such as Biology, Physics, Biomedical Sciences, Chemistry, Agrarian Sciences, Engineering, Mathemakics, Social, Health and Earth Sciences.