Slađana Đorđević, Dušan Ćoćić, Muntadar Al-Yassiri, Slavko Radenković, Ralph Puchta
{"title":"Electronic structure and aromaticity of [12]infinitene: A DFT study","authors":"Slađana Đorđević, Dušan Ćoćić, Muntadar Al-Yassiri, Slavko Radenković, Ralph Puchta","doi":"10.5937/kgjsci2345029d","DOIUrl":null,"url":null,"abstract":"The electronic structure and aromaticity of the [12]infinitene molecule (1) and its formation via the Mallory reaction were studied using density functional theory (DFT). The examined reaction is based on a stepwise cyclization process. The nucleus-independent chemical shifts (NICS) were used to assess the aromatic character of the chemical species involved in the examined reactions. In addition, NICS-Scan, 2D and 3D multidimensional off-nucleus siso(r) magnetic shielding scans were also employed to examine the aromaticity of 1. It was found that the formation of 1 is an endothermal process, as a result of the opposed stabilizing effects of aromaticity and destabilizing effects of planarity distortions found in molecules included in the considered reaction.","PeriodicalId":17829,"journal":{"name":"Kragujevac Journal of Science","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Kragujevac Journal of Science","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.5937/kgjsci2345029d","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
The electronic structure and aromaticity of the [12]infinitene molecule (1) and its formation via the Mallory reaction were studied using density functional theory (DFT). The examined reaction is based on a stepwise cyclization process. The nucleus-independent chemical shifts (NICS) were used to assess the aromatic character of the chemical species involved in the examined reactions. In addition, NICS-Scan, 2D and 3D multidimensional off-nucleus siso(r) magnetic shielding scans were also employed to examine the aromaticity of 1. It was found that the formation of 1 is an endothermal process, as a result of the opposed stabilizing effects of aromaticity and destabilizing effects of planarity distortions found in molecules included in the considered reaction.