{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T12:13:51Z","timestamp":1777464831201,"version":"3.51.4"},"reference-count":120,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2012,11,23]],"date-time":"2012-11-23T00:00:00Z","timestamp":1353628800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2013,1,7]]},"abstract":"Abstract<\/jats:title>A one\u2010pot template condensation of 2\u2010(2\u2010(dicyanomethylene)hydrazinyl)benzenesulfonic acid (H2<\/jats:sub>L1<\/jats:sup>, 1<\/jats:bold>) or 2\u2010(2\u2010(dicyanomethylene)hydrazinyl)benzoic acid (H2<\/jats:sub>L2<\/jats:sup>, 2<\/jats:bold>) with methanol (a), ethylenediamine (b), ethanol (c) or water (d) on copper(II), led to a variety of metal complexes, that is, mononuclear [Cu(H2<\/jats:sub>O)2<\/jats:sub>(\u03baO<\/jats:italic>1<\/jats:sup>,\u03baN<\/jats:italic>2<\/jats:sup>\u2009L1a<\/jats:sup>] (3<\/jats:bold>) and [Cu(H2<\/jats:sub>O)(\u03baO<\/jats:italic>1<\/jats:sup>,\u03baN<\/jats:italic>3<\/jats:sup>\u2009L1b<\/jats:sup>)] (4<\/jats:bold>), tetranuclear [Cu4<\/jats:sub>(1\u2009\u03baO<\/jats:italic>1<\/jats:sup>,\u03baN<\/jats:italic>2<\/jats:sup>:2\u2009\u03baO<\/jats:italic>1<\/jats:sup>\u2009L2a<\/jats:sup>)3<\/jats:sub>\u2010(1\u2009\u03baO<\/jats:italic>1<\/jats:sup>, \u03baN<\/jats:italic>2<\/jats:sup>:2\u2009\u03baO<\/jats:italic>2<\/jats:sup>\u2009L2a<\/jats:sup>)] (5<\/jats:bold>), [Cu2<\/jats:sub>(H2<\/jats:sub>O)(1\u2009\u03baO<\/jats:italic>1<\/jats:sup>, \u03baN<\/jats:italic>2<\/jats:sup>:2\u2009\u03baO<\/jats:italic>1<\/jats:sup>\u2009L2c<\/jats:sup>)\u2010(1\u2009\u03baO<\/jats:italic>1<\/jats:sup>,1\u2009\u03baN<\/jats:italic>2<\/jats:sup>:2\u2009\u03baO<\/jats:italic>1<\/jats:sup>,2\u2009\u03baN<\/jats:italic>1<\/jats:sup>\u2010 L2c<\/jats:sup>)]2<\/jats:sub> (6<\/jats:bold>) and [Cu2<\/jats:sub>(H2<\/jats:sub>O)2<\/jats:sub>(\u03baO<\/jats:italic>1<\/jats:sup>,\u03baN<\/jats:italic>2<\/jats:sup>\u2010 L1dd<\/jats:sup>)\u2010(1\u2009\u03baO<\/jats:italic>1<\/jats:sup>,\u03baN<\/jats:italic>2<\/jats:sup>:2\u2009\u03baO<\/jats:italic>1<\/jats:sup>\u2009L1dd<\/jats:sup>)(\u03bc\u2010H2<\/jats:sub>O)]2<\/jats:sub>\u22c5<\/jats:bold> 2\u2009H2<\/jats:sub>O (7\u22c5<\/jats:bold>2\u2009H2<\/jats:sub>O), as well as polymer\u2010 ic [Cu(H2<\/jats:sub>O)(\u03baO<\/jats:italic>1<\/jats:sup>,1\u2009\u03baN<\/jats:italic>2<\/jats:sup>:2\u2009\u03baN<\/jats:italic>1<\/jats:sup>\u2009L1c<\/jats:sup>)]n<\/jats:italic><\/jats:sub> (8<\/jats:bold>) and [Cu(NH2<\/jats:sub>C2<\/jats:sub>H5<\/jats:sub>)(\u03baO<\/jats:italic>1<\/jats:sup>,1\u2009\u03baN<\/jats:italic>2<\/jats:sup>:2\u2009\u03baN<\/jats:italic>1<\/jats:sup>L2a<\/jats:sup>)]n<\/jats:italic><\/jats:sub> (9<\/jats:bold>). The ligands 2\u2010SO3<\/jats:sub>H\u2010C6<\/jats:sub>H4<\/jats:sub>\u2010(NH)N\uf8feC{(CN)[C(NH2<\/jats:sub>)\u2010(\uf8feNCH2<\/jats:sub>CH2<\/jats:sub>NH2<\/jats:sub>)]} (H2<\/jats:sub>L1b<\/jats:sup>, 10<\/jats:bold>), 2\u2010CO2<\/jats:sub>H\u2010C6<\/jats:sub>H4<\/jats:sub>\u2010(NH)N\uf8fe{C(CN)[C(OCH3<\/jats:sub>)\u2010(\uf8feNH)]} (H2<\/jats:sub>L2a<\/jats:sup>, 11<\/jats:bold>) and 2\u2010SO3<\/jats:sub>H\u2010C6<\/jats:sub>H4<\/jats:sub>\u2010(NH)N\uf8feC{C(\uf8feO)\u2010(NH2<\/jats:sub>)}2<\/jats:sub> (H2<\/jats:sub>L1dd<\/jats:sup>, 12<\/jats:bold>) were easily liberated upon respective treatment of 4<\/jats:bold>, 5<\/jats:bold> and 7<\/jats:bold> with HCl, whereas the formation of cyclic zwitterionic amidine 2\u2010(SO3<\/jats:sub>\u2212<\/jats:sup>)\uf8ffC6<\/jats:sub>H4<\/jats:sub>\uf8ffN\uf8feNC(\uf8ffC\uf8fe(NH+<\/jats:sup>)CH2<\/jats:sub>CH2<\/jats:sub>NH)(\uf8feCNHCH2<\/jats:sub>CH2<\/jats:sub>NH) (13<\/jats:bold>) was observed when 1<\/jats:bold> was treated with ethylenediamine. The hydrogen bond\u2010induced E<\/jats:italic>\/Z<\/jats:italic> isomerization of the (HL1d<\/jats:sup>)\u2212<\/jats:sup> ligand occurs upon conversion of [{Na(H2<\/jats:sub>O)2<\/jats:sub>(\u03bc\u2010H2<\/jats:sub>O)2<\/jats:sub>}(HL1d<\/jats:sup>)]n<\/jats:italic><\/jats:sub> (14<\/jats:bold>) to [Cu(H2<\/jats:sub>O)6<\/jats:sub>][HL1d<\/jats:sup>]2<\/jats:sub>\u22c5<\/jats:bold>2\u2009H2<\/jats:sub>O (15<\/jats:bold>) and [{CuNa(H2<\/jats:sub>O)\u2010(\u03baN<\/jats:italic>1<\/jats:sup>,1\u2009\u03baO<\/jats:italic>2<\/jats:sup>:2\u2009\u03baO<\/jats:italic>1<\/jats:sup>\u2009L1d<\/jats:sup>)2<\/jats:sub>}K0.5<\/jats:sub>(\u03bc\u2010O)2<\/jats:sub>]n<\/jats:italic>\u22c5<\/jats:bold>H2<\/jats:sub>O (16<\/jats:bold>). The synthesized complexes 3<\/jats:bold>\u20139<\/jats:bold> are catalyst precursors for both the selective oxidation of primary and secondary alcohols (to the corresponding carbonyl compounds) and the following diastereoselective nitroaldol (Henry) reaction, with typical yields of 80\u201399\u2009%.<\/jats:p>","DOI":"10.1002\/chem.201203254","type":"journal-article","created":{"date-parts":[[2012,11,23]],"date-time":"2012-11-23T15:55:25Z","timestamp":1353686125000},"page":"588-600","source":"Crossref","is-referenced-by-count":75,"title":["Template Syntheses of Copper(II) Complexes from Arylhydrazones of Malononitrile and their Catalytic Activity towards Alcohol Oxidations and the Nitroaldol Reaction: Hydrogen Bond\u2010Assisted Ligand Liberation and E<\/i>\/Z<\/i> Isomerisation"],"prefix":"10.1002","volume":"19","author":[{"given":"Maximilian N.","family":"Kopylovich","sequence":"first","affiliation":[]},{"given":"Archana","family":"Mizar","sequence":"additional","affiliation":[]},{"given":"M. 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