Premium
Further crystallographic evidence of NH· · ·π (system) and CO· · ·π (system) interactions: The structures of bis(diarylhydrazonecarbonyl)methylene derivatives [{ArPhCNNH—C(O)} 2 CH 2 ] (Ar = Ph, 2‐C 5 H 4 N, 2‐C 4 H 3 S)
Author(s) -
Ganis Paolo,
Valle Giovanni,
Pandolfo Luciano,
Bertani Roberta,
Visentin Fabiano
Publication year - 1999
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/(sici)1097-0282(199906)49:7<541::aid-bip1>3.0.co;2-6
Subject(s) - chemistry , intramolecular force , intermolecular force , methylene , hydrogen bond , crystallography , stereochemistry , medicinal chemistry , molecule , organic chemistry
In this study are reported the syntheses of three bis(diarylhydrazonecarbonyl)methylene derivatives [{ArPhCNNHC(O)} 2 CH 2 ] [Ar = 2C 5 H 4 N (5), C 6 H 5 (6), and 2‐C 4 H 3 S (7)], obtained by condensation of corresponding hydrazones with carbon suboxide, C 3 O 2 . The solid‐state self‐assembly of these carbonyl derivatives, giving rise to polymeric and dimeric networks, is described. In the formation of these structural features, in addition to N—H· · ·OC intermolecular hydrogen bonds, stabilizing intramolecular NH· · · π (systems) and intermolecular CO· · ·π (systems) interactions also seem to play an important role. Solution 1 H‐nmr data of compounds 5–7 indicate that the polymeric and dimeric structures are not maintained in solution and show the occurrence of keto‐enolic equilibria. © 1999 John Wiley & Sons, Inc. Biopoly 49: 541–549, 1999