Deep-cavity resorcinarenes dimerize through hydrogen bonding and self-inclusion

被引：67

作者：

Ma, SH

Rudkevich, DM

Rebek, J ^{[1
]}

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 20期

关键词：

D O I：

10.1021/ja980418l

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of new resorcinarene derivatives featuring extended sides and self-complementary hydrogen-bonding sites is described. Dimerization occurs in solvents such as toluene-d(8), and large cavities result. The dimerization constant K-D = 1700 +/- 250 M-1 was determined, and the cavity of the dimer was found to encapsulate two heptyl or octyl chains of the subunits. It is proposed that hydrogen bonding and self-inclusion are responsible for the large and compensating thermodynamic parameters for dimerization: Delta H = -20.9 +/- 1.3 kcal mol(-1) and Delta S = -58 +/- 5 cal mol(-1) K-1.

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页码：4977 / 4981

页数：5

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