Synthesis and NMR studies on a C3-symmetrical triquinolina triscationic bicyclophane.
[structure: see text] Two-step syntheses of triple-bridged triscationic bicyclophanes 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 C3 symmetry and the other with C1 symmetry. The C3-symmetrical derivative is 1.94 kcal mol(-1) more stable than its C1-symmetrical one. This energy difference is sufficient to consider the former and its enantiomer the only two conformations existing in solution at room temperature.
Conejo-García
Ana
A
Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, c/Campus de Cartuja, s/n, 18071 Granada, Spain.
Campos
Joaquín
J
Eder
Carmen
C
Entrena
Antonio
A
Gallo
Miguel A
MA
Espinosa
Antonio
A