4.8 Article

Chiral helicity induced by hydrogen bonding and chirality of podand histidyl moieties

Journal

ORGANIC LETTERS
Volume 3, Issue 10, Pages 1459-1461

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0100327

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[GRAPHICS] The single-crystal X-ray structure determination of N,N ' -bis{(S)-(+)-1-methoxycarbonyl-2(4-imidazolyl)ethyl}-2,6-pyridinedicarboxamide (L-BHisPA) and the D-isomer (D-BHisPA) derived from the corresponding chiral histidine revealed a left- and right-handed helical conformation, respectively, through intramolecular hydrogen bonding and chirality of the podand histidyl moieties, Furthermore, each helical molecule is connected by continuous intermolecular hydrogen bonds to afford a left or right handed helical assembly, respectively, in the crystal packing.

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