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N,N′-Bis[(R)-2-hydroxy-2-phenylethyl]-N,N′-bis[(S)-1-phenylethyl]pyridine-2,6-dicarboxamide: stabilization of an asymmetric conformer through the formation of a double intramolecular hydrogen bond

✍ Scribed by Sosa-Rivadeneyra, Martha ;Quintero, Leticia ;Parrodi, Cecilia Anaya de ;Juaristi, Eusebio ;Bernès, Sylvain

Publisher: International Union of Crystallography
Year: 2005
Tongue: English
Weight: 271 KB
Volume: 61
Category: Article
ISSN: 1600-5368
DOI: 10.1107/s160053680500228x

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✦ Synopsis

The title compound, C 39 H 39 N 3 O 4 , although having potential C 2 molecular symmetry, crystallizes as an asymmetric conformer, due to a couple of strong intramolecular hydrogen bonds involving hydroxyl groups and a pyridine N atom. This geometrical feature explains why this compound behaves as a poor chiral inductor for asymmetric synthesis.

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N,N′-Bis­[(R)-2-hydroxy-2-phenyl­ethyl]-N,N′-bis­[(S)-1-phenyl­ethyl]­pyridine-2,6-dicarbox­amide: stabilization of an asymmetric conformer through the formation of a double intramolecular hydrogen bond

✦ Synopsis

N,N′-Bis[(R)-2-hydroxy-2-phenylethyl]-N,N′-bis[(S)-1-phenylethyl]pyridine-2,6-dicarboxamide: stabilization of an asymmetric conformer through the formation of a double intramolecular hydrogen bond