Understanding the driving force for the molecular recognition of S6-corona[3]arene[3]pyridazine toward organic ammonium cations,Organic Chemistry Frontiers

当前位置： X-MOL 学术 › Org. Chem. Front. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Understanding the driving force for the molecular recognition of S6-corona[3]arene[3]pyridazine toward organic ammonium cations
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-11-15 00:00:00 , DOI: 10.1039/c7qo00900c
Meng-Yao Zhao _{1,

2,

3,

4,

5} , Qing-Hui Guo _{1,

2,

3,

4,

5} , Mei-Xiang Wang _{1,

2,

3,

4,

5}

Affiliation

The molecular recognition of S₆-corona[3]arene[3]pyridazine toward various N-alkyl ammonium cations was systematically studied by means of ITC titration, NMR spectroscopy, mass spectrometry and X-ray crystallography. As a powerful and selective macrocyclic host molecule, S₆-corona[3]arene[3]pyridazine was able to form dominantly 1 : 1 complexes with cations in a mixture of CH₃CN and 1,2-dichloroethane (v : v = 1 : 1) giving association constants in the range of (1.08 ± 0.01) × 10³ M⁻¹ to (1.48 ± 0.11) × 10⁵ M⁻¹. In all cases, the favorable host–guest complexation processes were driven by the combination of beneficial enthalpy and entropy effects. While the enthalpy effect was attributable to the multiple non-covalent bond attractions such as lpe/π, π/π and nonconventional hydrogen bonds between host and guest, the entropy increase was most likely due to the desolvation of the guests.

中文翻译：

理解分子识别S6-电晕[3]芳烃[3]哒嗪对有机铵阳离子的驱动力

通过ITC滴定，NMR光谱，质谱和X射线晶体学系统研究了S _6-电晕[3]芳烃[3]哒嗪对各种N-烷基铵阳离子的分子识别。作为一种功能强大且具有选择性的大环主体分子，S _6-电晕[3]芳烃[3]哒嗪在CH ₃ CN和1,2-二氯乙烷的混合物中能与阳离子形成占优势的1：1配合物（v：v = 1：1）给出缔合常数，范围为（1.08±0.01）×10 ³ M ^-1至（1.48±0.11）×10 ⁵ M ^-1。在所有情况下，有利的宿主-客体复合过程都是由有益的焓和熵效应共同驱动的。尽管焓效应归因于主体和客体之间的多个非共价键吸引物，如lpe /π，π/π和非常规氢键，但熵的增加最有可能是由于客体的去溶剂化。

更新日期：2017-11-23

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11