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通过β-二羰基化合物对三聚氯氰的亲核取代以及随后的互变异构作用实现分子内多氢键框架的环状连接。

Circular linkage of intramolecular multi-hydrogen bonding frameworks through nucleophilic substitutions of β-dicarbonyls onto cyanuric chloride and subsequent tautomerisation.

作者信息

Awatani Ayano, Suzuki Masaaki

机构信息

Graduate School of Natural Science and Technology, Shimane University 1060 Nishikawatsu-cho Matsue Shimane 690-8504 Japan

出版信息

RSC Adv. 2020 Oct 23;10(64):39033-39036. doi: 10.1039/d0ra07677e. eCollection 2020 Oct 21.

Abstract

Nucleophilic substitution reactions of cyanuric chloride with a series of β-dicarbonyls give triply β-dicarbonyl-embedded 1,3,5-triazines. Their subsequent but spontaneous tautomeric transformation leads to circularly linked, intramolecular, multi-hydrogen bonding networks. Their structural elucidation by X-ray crystallography showed elongated double bonds and shortened single bonds. This is likely due to a resonance hybrid formed tautomerisation and simultaneous proton transfer.

摘要

三聚氯氰与一系列β - 二羰基化合物的亲核取代反应生成了含有三个β - 二羰基的1,3,5 - 三嗪。随后它们自发的互变异构转变导致了环状连接的分子内多氢键网络的形成。通过X射线晶体学对其结构的解析表明存在双键伸长和单键缩短的现象。这可能是由于互变异构和同时发生的质子转移形成了共振杂化体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08b6/9057380/7348f03e9a2a/d0ra07677e-c1.jpg

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