{"title":"Stabilization of cyclo-N6 by insertion into [18]-annulene: a DFT study","authors":"Fabio Pichierri","doi":"10.1007/s11224-024-02394-2","DOIUrl":null,"url":null,"abstract":"<div><p>The elusiveness of hexazine (a.k.a. hexaazabenzene) and its perhydrogenated derivative, hexazinane, prompted the author of this paper to investigate the possibility of stabilizing the six-membered nitrogen ring by inserting it into [18]-annulene. The resulting compound is made of a central N<sub>6</sub> ring surrounded by an outer ring of 18 carbon atoms that prevents its decomposition into dinitrogen. The N<sub>6</sub> ring is non-planar and with a chair-like conformation that does not undergo conformational isomerization. The designed molecule can be stabilized either by oxidation to a hexa-oxide derivative or by coordination of ZnCl<sup>+</sup>. Furthermore, a triangle-shaped macrocyclic isomer made of three pyridazine moieties connected to each other by ethylene bridges represents a possible precursor in the synthesis of the N<sub>6</sub>-embedded hydrocarbon. By employing an alkali or alkaline-earth metal cation that coordinates the three pyridazine monomers it becomes possible to bring their nitrogen atoms in close proximity so that a subsequent aromatic fusion reaction could be attempted.</p></div>","PeriodicalId":780,"journal":{"name":"Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11224-024-02394-2","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The elusiveness of hexazine (a.k.a. hexaazabenzene) and its perhydrogenated derivative, hexazinane, prompted the author of this paper to investigate the possibility of stabilizing the six-membered nitrogen ring by inserting it into [18]-annulene. The resulting compound is made of a central N6 ring surrounded by an outer ring of 18 carbon atoms that prevents its decomposition into dinitrogen. The N6 ring is non-planar and with a chair-like conformation that does not undergo conformational isomerization. The designed molecule can be stabilized either by oxidation to a hexa-oxide derivative or by coordination of ZnCl+. Furthermore, a triangle-shaped macrocyclic isomer made of three pyridazine moieties connected to each other by ethylene bridges represents a possible precursor in the synthesis of the N6-embedded hydrocarbon. By employing an alkali or alkaline-earth metal cation that coordinates the three pyridazine monomers it becomes possible to bring their nitrogen atoms in close proximity so that a subsequent aromatic fusion reaction could be attempted.
期刊介绍:
Structural Chemistry is an international forum for the publication of peer-reviewed original research papers that cover the condensed and gaseous states of matter and involve numerous techniques for the determination of structure and energetics, their results, and the conclusions derived from these studies. The journal overcomes the unnatural separation in the current literature among the areas of structure determination, energetics, and applications, as well as builds a bridge to other chemical disciplines. Ist comprehensive coverage encompasses broad discussion of results, observation of relationships among various properties, and the description and application of structure and energy information in all domains of chemistry.
We welcome the broadest range of accounts of research in structural chemistry involving the discussion of methodologies and structures,experimental, theoretical, and computational, and their combinations. We encourage discussions of structural information collected for their chemicaland biological significance.