A structural study of 4-aminoantipyrine and six of its Schiff base derivatives

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dc.citation.doi10.1107/S2053229614027247en_ZA
dc.citation.epage109en_ZA
dc.citation.issue2en_ZA
dc.citation.spage103en_ZA
dc.contributor.authorMnguni, M.J.
dc.contributor.authorLemmerer, A.
dc.date.accessioned2016-11-22T13:26:18Z
dc.date.available2016-11-22T13:26:18Z
dc.date.issued2015-02
dc.description.abstractSix derivatives of 4-amino-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one (4-aminoantipyrine), C11H13N3O, (I), have been synthesized and structurally characterized to investigate the changes in the observed hydrogen-bonding motifs compared to the original 4-aminoantipyrine. The derivatives were synthesized from the reactions of 4-aminoantipyrine with various aldehyde-, ketone- and ester-containing molecules, producing (Z)-methyl 3-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]but-2-enoate, C16H19N3O3, (II), (Z)-ethyl 3-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]but-2-enoate, C17H21N3O3, (III), ethyl 2-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]cyclohex-1-enecarboxylate, C20H25N3O3, (IV), (Z)-ethyl 3-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]-3-phenylacrylate, C22H23N3O3, (V), 2-cyano-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, C14H14N4O2, (VI), and (E)-methyl 4-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]methyl}benzoate, C20H19N3O3, (VII). The asymmetric units of all these compounds have one molecule on a general position. The hydrogen bonding in (I) forms chains of molecules via intermolecular N-H⋯O hydrogen bonds around a crystallographic sixfold screw axis. In contrast, the formation of enamines for all derived compounds except (VII) favours the formation of a six-membered intramolecular N-H⋯O hydrogen-bonded ring in (II)-(V) and an intermolecular N-H⋯O hydrogen bond in (VI), whereas there is an intramolecular C-H⋯O hydrogen bond in the structure of imine (VII). All the reported compounds, except for (II), feature π-π interactions, while C-H⋯π interactions are observed in (II), C-H⋯O interactions are observed in (I), (III), (V) and (VI), and a C-O⋯π interaction is observed in (II).en_ZA
dc.description.librarianSP2016en_ZA
dc.description.urlhttp://journals.iucr.org/c/issues/2015/02/00/fn3185/en_ZA
dc.identifier.citationMnguni, M.J. and Lemmerer, A. 2015. A structural study of 4-aminoantipyrine and six of its Schiff base derivatives. Acta Crystallographica Section C: Structural Chemistry 71(2), pp.103-109.en_ZA
dc.identifier.issn2053-2296
dc.identifier.urihttp://hdl.handle.net/10539/21472
dc.journal.titleActa Crystallographica Section C: Structural Chemistryen_ZA
dc.journal.volume71en_ZA
dc.language.isoenen_ZA
dc.publisherInternational Union of Crystallographyen_ZA
dc.subject4-aminoantipyrineen_ZA
dc.subjectanti-inflammatory agenten_ZA
dc.subjectbiological activityen_ZA
dc.subjectcrystal structureen_ZA
dc.subjecthydrogen bondingen_ZA
dc.subjectSchiff basesen_ZA
dc.subjectπ-bondingen_ZA
dc.titleA structural study of 4-aminoantipyrine and six of its Schiff base derivativesen_ZA
dc.typeArticleen_ZA
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