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由烷氧基硅烷和氯硅烷合成芳基取代硅二醇和硅三醇及其氢键模式

Synthesis and Hydrogen-Bond Patterns of Aryl-Group Substituted Silanediols and -triols from Alkoxy- and Chlorosilanes.

作者信息

Kannengießer Jan-Falk, Briesenick Max, Meier Dennis, Huch Volker, Morgenstern Bernd, Kickelbick Guido

机构信息

Inorganic Solid-State Chemistry, Saarland University Campus, Building C4 1, 66123, Saarbrücken, Germany.

出版信息

Chemistry. 2021 Nov 25;27(66):16461-16476. doi: 10.1002/chem.202102729. Epub 2021 Oct 21.

DOI:10.1002/chem.202102729
PMID:34545975
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9297978/
Abstract

Organosilanols typically show a high condensation tendency and only exist as stable isolable molecules under very specific steric and electronic conditions at the silicon atom. In the present work, various novel representatives of this class of compounds were synthesized by hydrolysis of alkoxy- or chlorosilanes. Phenyl, 1-naphthyl, and 9-phenanthrenyl substituents at the silicon atom were applied to systematically study the influence of the aromatic substituents on the structure and reactivity of the compounds. Chemical shifts in Si NMR spectroscopy in solution, correlated well with the expected electronic situation induced by the substitution pattern on the Si atom. H NMR studies allowed the detection of strong intermolecular hydrogen bonds. Single-crystal X-ray structures of the alkoxides and the chlorosilanes are dominated by π-π interactions of the aromatic systems, which are substituted by strong hydrogen bonding interactions representing various structural motifs in the respective silanol structures.

摘要

有机硅醇通常表现出很高的缩合倾向，并且只有在硅原子处于非常特殊的空间和电子条件下才以稳定的可分离分子形式存在。在本工作中，通过烷氧基硅烷或氯硅烷的水解合成了这类化合物的各种新型代表物。在硅原子上引入苯基、1-萘基和9-菲基取代基，以系统地研究芳基取代基对化合物结构和反应性的影响。溶液中硅核磁共振光谱的化学位移与硅原子上取代模式所诱导的预期电子状况密切相关。氢核磁共振研究能够检测到强烈的分子间氢键。醇盐和氯硅烷的单晶X射线结构主要由芳环体系的π-π相互作用主导，在相应的硅醇结构中，这些相互作用被代表各种结构 motif 的强氢键相互作用所取代。

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