Structural chemistry of oximes

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dc.contributor.author Aakeröy, Christer B.
dc.contributor.author Sinha, Abhijeet Shekhar
dc.contributor.author Epa, Kanishka N.
dc.contributor.author Chopade, Prashant D.
dc.contributor.author Smith, Michelle M.
dc.contributor.author Desper, John
dc.date.accessioned 2013-07-30T18:33:15Z
dc.date.available 2013-07-30T18:33:15Z
dc.date.issued 2013-07-30
dc.identifier.uri http://hdl.handle.net/2097/16003
dc.description.abstract Oximes (RR'C=N-OH) represent an important class of organic compounds with a wide range of practical applications, but a systematic examination of the structural chemistry of such compounds has so far not been carried out. Herein, we report a systematic analysis of intermolecular homomeric oxime•••oxime interactions, and identify hydrogen-bond patterns for four major categories of oximes (R' = -H, -CH[subscript 3], -NH[subscript 2], -CN), based on all available structural data in the CSD, complemented by six new relevant crystal structures. The structural behavior of oximes examined here, can be divided into four groups depending on which type of predominant oxime•••oxime interactions they present in the solid-state; (i) O-H•••N dimers (R[superscript 2][subscript 2](6)), (ii) O-H•••N catemers (C(3)), (iii) O-H•••O catemers (C(2)), and (iv) oximes in which the R' group accepts a hydrogen bond from the oxime moiety catemers (C(6)). The electronic and structural effects of the substituent (R') on the resulting assembly has been explored in detail in order to rationalize the connection between molecular structure and supramolecular assembly. en_US
dc.language.iso en_US en_US
dc.relation.uri http://pubs.acs.org/doi/full/10.1021/cg4005246 en_US
dc.rights Permission to archive granted by Crystal Growth and Design, June 21, 2013. This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in Crystal Growth & Design, copyright © American Chemical Society after peer review. To access the final edited and published work see http://pubs.acs.org/doi/full/10.1021/cg4005246 en_US
dc.subject Oximes en_US
dc.subject Structural chemistry en_US
dc.title Structural chemistry of oximes en_US
dc.type Article (author version) en_US
dc.date.published 2013 en_US
dc.citation.doi doi:10.1021/cg4005246 en_US
dc.citation.epage 2695 en_US
dc.citation.issue 6 en_US
dc.citation.jtitle Crystal Growth & Design en_US
dc.citation.spage 2687 en_US
dc.citation.volume 13 en_US
dc.contributor.authoreid aakeroy en_US
dc.contributor.authoreid desperj en_US


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