Influence of the size of upper and lower rim substituents on the fluxional and complexation behaviour of calix[5]arenes

被引：26

作者：

Ferguson, G

Notti, A

Pappalardo, S

Parisi, MF

Spek, AL

机构：

[1] Univ Guelph, Dept Chem & Biochem, Guelph, ON N1G 2W1, Canada

[2] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy

[3] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

[4] Univ Utrecht, Bijvoet Ctr, Dept Crystal & Struct Chem, Utrecht, Netherlands

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 14期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(98)00106-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A comparative study on a series of penta-O-alkylated p-H-calix[5]arenes 1b-e and p-tert-butylcalix[5]arenes 1g-m shows that the former are inherently mobile and adopt in solution non-cone conformations. The 1,2-alternate conformation for penta-O-benzyl ether 1c was proven by single-crystal X-ray analysis. VT-NMR studies on 1c-e have provided the first experimental evidence that conformational interconversion occurs via the p-phenyl-through-the-annulus mechanism with Delta G double dagger in the range 17.9-18.8 kcal mol(-1). Unlike the corresponding tert-butylated counterparts, pH-calix[5]arenes are unable to form 1:1 endo-calix complexes with primary unbranched alkylammonium cations. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1965 / 1968

页数：4

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