Matheus P DE Freitas, Ana Júlia F Souza, Julliane Yoneda, Diego P Sangi
{"title":"A theoretical view on the stereochemistry of 1,3-benzoxazol-2-(3H)-ylidenes obtained from double vinylic substitution.","authors":"Matheus P DE Freitas, Ana Júlia F Souza, Julliane Yoneda, Diego P Sangi","doi":"10.1590/0001-3765202420240156","DOIUrl":null,"url":null,"abstract":"<p><p>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.</p>","PeriodicalId":7776,"journal":{"name":"Anais da Academia Brasileira de Ciencias","volume":null,"pages":null},"PeriodicalIF":1.1000,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Anais da Academia Brasileira de Ciencias","FirstCategoryId":"103","ListUrlMain":"https://doi.org/10.1590/0001-3765202420240156","RegionNum":4,"RegionCategory":"综合性期刊","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/1/1 0:00:00","PubModel":"eCollection","JCR":"Q3","JCRName":"MULTIDISCIPLINARY SCIENCES","Score":null,"Total":0}
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.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
