A versatile ternary ion pair complex of 2′-amino-1,1′-binaphthalen-2-ol for sensing enantiomers and assignment of absolute configuration

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-10-15 DOI:10.1016/j.tetasy.2017.09.016

Anamalagundam Lakshmipriya , Gaonkar Sumana , Nagaraja Rao Suryaprakash

引用次数: 3

Abstract

2′-Amino-1,1′-binaphthalen-2-ol (NOBIN) serves as a versatile chiral solvating agent (CSA) in the presence of trifluoromethanesulfonic acid (TFMS). The formation of a ternary complex has been established by NMR, UV–Vis, fluorescence and IR studies. The mechanism of interactions among the three components in the ternary complex has been proposed and the ternary complex structures of different diastereomers have been established by DFT based theoretical calculations. The present protocol has its ubiquity not only in the analysis of the enantiomeric composition of molecules possessing diverse functionalities, but also in determining the stereospecific assignment of hydroxy acids.

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2 ' -氨基-1,1 ' -二萘-2-醇的多功能三元离子对配合物，用于感应对映体和绝对构型的分配

2 ' -氨基-1,1 ' -二萘-2-醇(NOBIN)在三氟甲烷磺酸(TFMS)存在下作为一种多用途手性溶剂化剂(CSA)。通过核磁共振、紫外-可见、荧光和红外研究，确定了三元配合物的形成。提出了三元配合物中三组分相互作用的机理，并通过基于DFT的理论计算建立了不同非对映体的三元配合物结构。该方法不仅适用于分析具有不同官能团的分子的对映体组成，而且适用于确定羟基酸的立体定向配位。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.