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Solvent‐ and Temperature‐Controlled In Situ Ligand Reactions Mediated by Cu II and 3′‐[( E )‐{[(1 S ,2 S )‐2‐Aminocyclohexyl]imino}methyl]‐4′‐hydroxy‐4‐biphenylcarboxlic Acid
Author(s) -
Chen Qihui,
Jiang Feilong,
Chen Lian,
Yang Ming,
Hong Maochun
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201104001
Subject(s) - ligand (biochemistry) , chemistry , nitration , solvent , crystal structure , single crystal , amination , crystallography , medicinal chemistry , copper , stereochemistry , organic chemistry , catalysis , biochemistry , receptor
Abstract Three new compounds, CuL, CuL′, and Cu 2 O 2 L′′ 2 (H 2 L=3′‐[( E )‐{[(1 S ,2 S )‐2‐aminocyclohexyl]imino}methyl]‐4′‐hydroxy‐4‐biphenylcarboxlic acid, H 2 L′=3′‐[( E )‐{[(1 S ,2 S )‐2‐aminocyclohexyl]imino}methyl]‐4′‐hydroxy‐5′‐nitro‐4‐biphenylcarboxlic acid, H 2 L′′=3′‐( N , N ‐dimethylamino methyl)‐4′‐hydroxy‐4‐biphenylcarboxlic acid), were selectively synthesized through a controlled in situ ligand reaction system mediated by copper(II) nitrate and H 2 L. Selective nitration was achieved by using different solvent mixtures under relatively mild conditions, and an interesting and economical reductive amination system in DMF/EtOH/H 2 O was also found. All crystal structures were determined by single‐crystal X‐ray diffraction analysis. Both CuL and CuL′ display chiral 1D chain structures, whereas Cu 2 O 2 L′′ 2 possesses a structure with 13×16 Å channels and a free volume of 41.4 %. The possible mechanisms involved in this in situ ligand‐controlled reaction system are discussed in detail.