Stabilization of cyclo-N6 by insertion into [18]-annulene: a DFT study

IF 2.1 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Structural Chemistry Pub Date : 2024-10-18 DOI:10.1007/s11224-024-02394-2
Fabio Pichierri
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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.

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通过插入 [18]-annulene 稳定环-N6:DFT 研究
己嗪(又名六氮苯)及其过氢化衍生物己嗪烷的难以捉摸,促使本文作者研究将六元氮环插入[18]-annulene,从而使其稳定的可能性。由此产生的化合物由一个由 18 个碳原子组成的外环包围着一个中心 N6 环,该外环可防止其分解成二氮。N6 环为非平面环,具有类似椅子的构象,不会发生构象异构化。所设计的分子可以通过氧化成六氧化物衍生物或配位 ZnCl+ 来稳定。此外,由三个哒嗪分子通过乙烯桥相互连接而成的三角形大环异构体是合成 N6 嵌入碳氢化合物的可能前体。通过使用碱金属或碱土金属阳离子来配位三个哒嗪单体,可以使它们的氮原子靠近,从而可以尝试随后的芳香融合反应。
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来源期刊
Structural Chemistry
Structural Chemistry 化学-化学综合
CiteScore
3.80
自引率
11.80%
发文量
227
审稿时长
3.7 months
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.
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