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Interplay between Resonance‐Assisted Hydrogen Bonding and Coordination in Sulfo‐Functionalized Arylhydrazones of Active Methylene Compounds
Author(s) -
Mahmudov Kamran T.,
Kopylovich Maximilian N.,
Guedes da Silva M. Fátima C.,
Pombeiro Armando J. L.
Publication year - 2014
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201402088
Subject(s) - chemistry , hydrogen bond , intermolecular force , crystallography , methylene , sodium , molecule , stereochemistry , medicinal chemistry , organic chemistry
The interaction of sodium(I) and copper(II) with sodium ( E,Z )‐2‐[2‐(1‐cyano‐2‐methoxy‐2‐oxoethylidene)hydrazinyl]benzenesulfonate (NaHL 1 ), sodium 4‐[2‐(2,4‐dioxopentan‐3‐ylidene)hydrazinyl]benzenesulfonate (NaHL 2 ), and sodium 2‐[2‐(2,4‐dioxopentan‐3‐ylidene)hydrazinyl]benzenesulfonate (NaHL 3 ) is studied on the basis of competition between intra‐ and intermolecular hydrogen bonding and coordination. The interplay between such interactions provides an unprecedented strategy towards an easy (( E , Z )→ E or Z ) isomeric resolution of NaHL 1 to give the new coordination polymers [Na(H 2 O) 2 (μ‐HL 1 )] n ( 1 ) ( E form) and [Na 2 (H 2 O) 4 (μ‐HL 1 ) 2 ] n ⋅ n H 2 O ( 2 ) ( Z form). It is also applied to the synthesis of the new compounds [Cu(H 2 O) 6 ](HL 2 ) 2 ⋅ 4 H 2 O ( 3 ) and [Cu(A)L 3 ] ⋅ H 2 O ( 4 ) (A=2‐(pyridin‐2‐yl)ethanol). The intra‐ and intermolecular structural relevance of hydrogen bonding is detailed by X‐ray diffraction.