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Sugar-substituted fluorous 1,2,3-triazoles: Helical twists in fluoroalkyl chains and their molecular association in the solid state and correlations with physicochemical properties
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2020-05-19 , DOI: 10.1016/j.jfluchem.2020.109536
Adnan I. Mohammed , Ahmed M.A. Ahmed , Mohan M. Bhadbhade , Junming Ho , Roger W. Read

This paper describes a novel study of thirty closely related polyfluoroalkyl-substituted glycosidyl-1,2,3-triazoles with systematic variations in the type of sugar, d-glucos-1′-yl or d-galactos-6′-yl derivatives, the protected or unprotected form of the sugar, the length and nature of linker groups to the triazole, the point of attachment and the atom of attachment between the substituent and the triazole, and the length of the perfluoroalkyl chain. It reports for the first time the molecular structure and crystal structures of three of the candidates, as defined by single crystal X-ray diffraction analysis, and compares melting point and specific optical rotation values, in combination with the diffraction, NMR spectroscopic and computational data to establish structural features, such as the helical twist of the fluoroalkyl chains, that influence physicochemical properties in the solid and solution states. The results provide a valuable reference source for practitioners in the field and will aid in the design of future materials.



中文翻译:

糖取代的氟1,2,3-三唑:氟烷基链中的螺旋扭曲及其在固态下的分子缔合及其与理化性质的关系

本文描述了对三十种密切相关的多氟烷基取代的糖苷基-1,2,3-三唑的新颖研究,这些糖的糖类,d-葡萄糖-1'-基或d-半乳糖-6'-基衍生物,糖的保护或未保护形式,与三唑的连接基团的长度和性质,取代基和三唑之间的连接点和连接原子以及其长度全氟烷基链。它首次报告了由单晶X射线衍射分析确定的三种候选分子的分子结构和晶体结构,并结合衍射,NMR光谱和计算数据比较了熔点和比旋光度值以建立结构特征,例如氟烷基链的螺旋形扭曲,从而影响固态和溶液态的物理化学性质。

更新日期:2020-05-19
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