Synthesis and NMR studies on a C3-symmetrical triquinolina triscationic bicyclophane

被引：12

作者：

Conejo-García, A ^{[1
]}

Campos, J ^{[1
]}

Eder, C ^{[1
]}

Entrena, A ^{[1
]}

Gallo, MA ^{[1
]}

Espinosa, A ^{[1
]}

机构：

[1] Fac Farm, Dept Quim Organ & Farmaceut, Granada 18071, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 14期

关键词：

D O I：

10.1021/jo050554q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two-step syntheses of triple-bridged triscationic bicyclo-phanes are presented. Molecular modeling has been undertaken by means of ab initio calculations (6-31G** level) on the triquinolina triscationic bicyclophane. This compound exists as two diastereomeric sets of enantiomers, one with C-3 symmetry and the other with C-1 symmetry. The C-3-symmetrical derivative is 1.94 kcal mol(-1) more stable than its C-1-symmetrical one. This energy difference is sufficient to consider the former and its enantiomer the only two conformations existing in solution at room temperature.

引用

页码：5748 / 5751

页数：4

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