Synthesis and NMR Studies on a C 3 -Symmetrical Triquinolina Triscationic Bicyclophane
2005; American Chemical Society; Volume: 70; Issue: 14 Linguagem: Inglês
10.1021/jo050554q
ISSN1520-6904
AutoresAna Conejo‐García, Joaquín M. Campos Rosa, C. Eder, Antonio Entrena, Miguel Á. Gallo, Antonio Espinosa,
Tópico(s)Supramolecular Chemistry and Complexes
Resumo[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.
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