Development of bis(2-picolyl)amine-zinc chelates for imidazole receptors

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en Routasalo, T. Helaja, J. Kavakka, J. Koskinen, A.M.P. 2016-09-23T08:24:51Z 2008
dc.identifier.citation Routasalo , T , Helaja , J , Kavakka , J & Koskinen , A M P 2008 , ' Development of bis(2-picolyl)amine-zinc chelates for imidazole receptors ' , European Journal of Organic Chemistry , no. 18 , pp. 3190-3199 . en
dc.identifier.issn 1434-193X
dc.identifier.other PURE UUID: e0e441f5-34af-4989-9870-99f2a24a67f5
dc.identifier.other PURE ITEMURL:
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dc.description.abstract New phenyl and phenol bis(2-picolyl)amine (Dpa) derivatives have been synthesized in order to generate zinc chelates for imidazole anion receptors. Previously, binuclear phenolic zinc and copper chelates have shown affinity for pyrophosphate and guanidine anions, respectively. Herein we report significant imidazole affinity increasing from 2.38106 to 2.90107 for phenol-bridged binuclear zinc–Dpa chelates, as evidenced by dynamic and titration 1H NMR studies. Among the Dpa chelates investigated, the zinc-coordinated phenol group plays a crucial role in the mechanism of anion binding. Low-temperature 1H NMR experiments suggest a σν-symmetric geometry for the imidazole chelate. Computational DFT studies at the B3LYP level of theory imply that imidazole binding displaces the phenol bridge between the zinc ions. en
dc.format.extent 3190-3199
dc.format.mimetype application/pdf
dc.language.iso en en
dc.relation.ispartofseries EUROPEAN JOURNAL OF ORGANIC CHEMISTRY en
dc.relation.ispartofseries issue 18 en
dc.rights openAccess en
dc.subject.other 116 Chemical sciences en
dc.title Development of bis(2-picolyl)amine-zinc chelates for imidazole receptors en
dc.type A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä fi
dc.description.version Peer reviewed en
dc.contributor.department Department of Chemistry en
dc.subject.keyword 116 Chemical sciences
dc.identifier.urn URN:NBN:fi:aalto-201609234374
dc.identifier.doi 10.1002/ejoc.200700926
dc.type.version acceptedVersion

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