Chiral Schiff base derivatives of calix[4]arene: synthesis and complexation studies with chiral and achiral amines

被引：27

作者：

Durmaz, Mustafa ^{[1
]}

Alpaydin, Sabri ^{[1
]}

Sirit, Abdulkadir ^{[1
]}

Yilmaz, Mustafa ^{[1
]}

机构：

[1] Selcuk Univ, Dept Chem, TR-42031 Konya, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 16期

关键词：

D O I：

10.1016/j.tetasy.2006.08.008

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Novel chiral Schiff base derivatives of calix[4]arenes 1-3 have been prepared from the reaction of 5,17-diformyl-25,27-dipropoxy-26,28-dihydroxycalix[4]arene 4 with (S)-(-)-1-phenylethylamine, (R)-(-)-1-cyclohexylethylamine, and (R)-(-)-2-heptylamine, respectively, by a convenient method in 69-80% yields. Spectrophotometric titrations have been performed in CHCl3 at 20-30 degrees C in order to obtain the binding constants (K) and thermodynamic quantities (Delta H and Delta S) for the stoichiometric 1:1 inclusion complexation of various amines with these new host compounds. The molecular recognition abilities and enantioselectivity for guests (R)- and (S)-alpha-phenylethylamine, 3-morpholinopropylamine and n-butylamine are discussed from a thermodynamic point of view. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2322 / 2327

页数：6

共 61 条

[1] Synthesis of selectively formylated calixarene ethers [J].