芳香族N-メチルアミドのcis型優先性の発見およびその分子構築への応用

概要

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Aromatic secondary amides such as benzanilide(1)exist in a trans-amide form both in the crystal and in the solution, whereas N-methylbenzanilide(2)exists in cis form in the crystal, and predominantly in a cis form in the solution. Similar cis conformational preferences were observed in aromatic N, N'-dimethlated ureas and guanidines, in which two aromatic rings are located face to face. The cis prferences of N-methylated amides, ureas and guanidines could be utilized to construct interesting aromatic architecture. N, N', N"-Trimethyl-N, N', N"-triphenyl-1, 3, 5-benzenetricarboxamide(20)and a cyclic triamide(24)have crystal structures in which three N-phenyl groups direct to the same orientation (syn conformation). 1, 2-Bis(N-benzoyl-N-methylamino)benzene (22), which have no fixed asymmetric center, afforded chiral crystals by simple recrystallization. Furthermore, aromatic multi-layered structures could be built and applied to obtain aromatic molecules which have potent DNA-binding ability.
2001-02-01