Aromatic Architecture Based on cis Conformational Preference of N-Methylated Amides.

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  • Ｎ‐メチル化アミドのシス型優先性と芳香族分子構築
  • N メチルカ アミド ノ シスガタ ユウセンセイ ト ホウコウゾク ブンシ コウチク

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Aromatic secondary amides such as benzanilide (1) exist in trans-amide form both in the crystal and in solution, whereas N-methylbenzanilide (2) exists in cis form in the crystal, and predominantly in cis form in various solutions. Similar cis conformational preferences were observed in the aromatic N, N'-dimethylated urea (4) and guanidine (7), in which two aromatic rings are located face-to-face. The cis conformations of N-methylated amides, ureas and guanidines could be utilized to construct interesting aromatic architecture. First, N, N', N″-trimethyl-N, N', N″-triphenyl-1, 3, 5-benzenetricarboxamide (12) and a cyclic triamide 14 have crystal structures in which three N-phenyl groups exist with the same orientation (syn conformation). Second, several aromatic amides which have no fixed asymmetric center afforded chiral crystals by simple recrystallization. In the case of 1, 2-bis (N-benzoyl-N-methylamino) benzene (18), two enantiomeric crystals could be distinguished morphologically or on the basis of symmetrical CD spectra in KBr, and by 1H-NMR in the presence of chiral 1, 1'-bi-2-naphthol. Third, aromatic multi-layered structures could be constructed by using N, N'-dimethylated urea or guanidino bonds. These unique layered structures could be applied to obtain aromatic molecules with potent DNA-binding ability.

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