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dc.contributor.authorShaibah, Mohammed A. E.
dc.contributor.authorYathirajan, Hemmige S., Asma
dc.contributor.authorManju, Nagaraja
dc.contributor.authorKalluraya, Balakrishna
dc.contributor.authorRathore, Ravindranath S.
dc.contributor.authorGlidewell, Christopher
dc.identifier.citationShaibah , M A E , Yathirajan , H S , . , A , Manju , N , Kalluraya , B , Rathore , R S & Glidewell , C 2020 , ' Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products ' , Acta Crystallographica Section E , vol. 76 , no. 3 , pp. 360-365 .
dc.identifier.otherPURE: 267395240
dc.identifier.otherPURE UUID: a65be6d7-ada9-4ca7-b418-02f60bdff105
dc.identifier.otherBibtex: Shaibah:zl2770
dc.identifier.otherScopus: 85081717316
dc.identifier.otherWOS: 000518844900014
dc.descriptionHSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.en
dc.description.abstractChalcones of type 4-XC6H4C(O)CH=CHC6H4(OCH2CCH)-4, where X = Cl, Br or MeO, have been converted to the corresponding 4,5-di­hydro­pyrazole-1-carbo­thio­amides using a cyclo­condensation reaction with thio­semicarbazide. The chalcones 1-(4-chloro­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13ClO2, (I), and 1-(4-bromo­phen­yl)-3-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one, C18H13BrO2, (II), are isomorphous, and their mol­ecules are linked into sheets by two independent C—Hπ(arene) inter­actions, both involving the same aryl ring with one C—H donor approaching each face. In each of the products (RS)-3-(4-chloro­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16ClN3OS, (IV), (RS)-3-(4-bromo­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C19H16BrN3OS, (V), and (RS)-3-(4-meth­oxy­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro­pyrazole-1-carbo­thio­amide, C20H19N3O2S, (VI), the reduced pyrazole ring adopts an envelope conformation with the C atom bearing the 4-prop-2-yn­yloxy)phenyl substituent, which occupies the axial site, displaced from the plane of the four ring atoms. Compounds (IV) and (V) are isomorphous and their mol­ecules are linked into chains of edge-fused rings by a combination of N—H···S and C—H···S hydrogen bonds. The mol­ecules of (VI) are linked into sheets by a combination of N—H···S, N—H···N and C—H···π(arene) hydrogen bonds. Comparisons are made with the structures of some related compounds.
dc.relation.ispartofActa Crystallographica Section Een
dc.rightsCopyright © 2020 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.en
dc.subjectHeterocyclic compoundsen
dc.subjectReduced pyrazolesen
dc.subjectCrystal structuresen
dc.subjectMolecular conformationen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assemblyen
dc.subjectQD Chemistryen
dc.titleConversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three productsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.description.statusPeer revieweden

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