Journal article
Hydrogen bond patterns in aromatic and aliphatic dioximes
New Journal of Chemistry, Vol.27(7), pp.184-194
06/30/2003
DOI: 10.1039/b301045g
Abstract
Despite their established hydrogen bonding capability, oxime functional groups (–C(R′)[double bond, length as m-dash]NOH) have received far less attention in supramolecular chemistry than their carboxyl and amide counterparts. Here we report a series of dioximes (R′[double bond, length as m-dash]H, CH3, NH2) for which hydrogen bonding patterns have been examined in the solid state to establish the reliability of hydrogen-bonded synthons available for use in supramolecular syntheses using oximes. In all cases, network structures were formed, most frequently propagated through oxime–oxime O–H⋯N hydrogen-bonded dimer formation [R22(6) graph set] and less often using C(3) chain or R44(12) ring arrangements. Even in the systems where R′ = NH2, robust and dominant oxime–oxime hydrogen bonding prevails, with amino groups playing a supporting role in network construction primarily via weaker N–H⋯O hydrogen bonds. The compounds studied are aromatic dioximes 1,3-C6H4(C(R′)[double bond, length as m-dash]NOH)21–3 and 1,4-C6H4(C(R′)[double bond, length as m-dash]NOH)24–6 (R′ = H, CH3, NH2), and aliphatic dioximes fumaramide dioxime 7 (R′ = NH2) and succinamide dioxime 8 (R′ = NH2).
Details
- Title: Subtitle
- Hydrogen bond patterns in aromatic and aliphatic dioximes
- Creators
- Eric A BrutonLee BrammerF Christopher Pigge - ChemistryChrister B AakeröyDestin S Leinen
- Resource Type
- Journal article
- Publication Details
- New Journal of Chemistry, Vol.27(7), pp.184-194
- DOI
- 10.1039/b301045g
- ISSN
- 1144-0546
- eISSN
- 1369-9261
- Number of pages
- 11
- Date published
- 06/30/2003
- Academic Unit
- Chemistry; Radiology
- Record Identifier
- 9984216671202771
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