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Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones : synthetic pathway, and the structures of six examples
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dc.contributor.author | Kiran Kumar, Haruvegowda | |
dc.contributor.author | Yathirajan, Hemmige S | |
dc.contributor.author | Asma | |
dc.contributor.author | Manju, Nagaraja | |
dc.contributor.author | Kalluraya, Balakrishna | |
dc.contributor.author | Rathore, Ravindranath S | |
dc.contributor.author | Glidewell, Christopher | |
dc.date.accessioned | 2021-07-12T10:30:16Z | |
dc.date.available | 2021-07-12T10:30:16Z | |
dc.date.issued | 2020-05-01 | |
dc.identifier.citation | Kiran Kumar , H , Yathirajan , H S , Asma , Manju , N , Kalluraya , B , Rathore , R S & Glidewell , C 2020 , ' Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones : synthetic pathway, and the structures of six examples ' , Acta Crystallographica Section E Crystallographic Communications , vol. 76 , no. 5 , pp. 683-691 . https://doi.org/10.1107/S2056989020005113 | en |
dc.identifier.issn | 2056-9890 | |
dc.identifier.other | PURE: 274689655 | |
dc.identifier.other | PURE UUID: efc72419-80ef-4f12-a077-8bf736307185 | |
dc.identifier.other | PubMed: 32431933 | |
dc.identifier.other | PubMedCentral: PMC7199250 | |
dc.identifier.other | WOS: 000533786100018 | |
dc.identifier.other | Scopus: 85084564409 | |
dc.identifier.uri | https://hdl.handle.net/10023/23522 | |
dc.description | HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years. | en |
dc.description.abstract | Five examples each of 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-ones and the corresponding 1-(4-azidophenyl)-3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones have been synthesized in a highly efficient manner, starting from a common source precursor, and structures have been determined for three examples of each type. In each of 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, C28H21ClN2O3, (Ib), the isomeric 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, (Ic), and 3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one, C32H24N2O3, (Ie), the molecules are linked into chains of rings, formed by two independent C—H⋯O hydrogen bonds in (Ib) and by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds in each of (Ic) and (Ie). There are no direction-specific intermolecular interactions in the structure of 1-(4-azidophenyl)-3-[3-methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C26H21N5O2, (IIa). In 1-(4-azidophenyl)-3-[5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C25H17Cl2N5O2, (IId), the dichlorophenyl group is disordered over two sets of atomic sites having occupancies 0.55 (4) and 0.45 (4), and the molecules are linked by a single C—H⋯O hydrogen bond to form cyclic, centrosymmetric R22(20) dimers. Similar dimers are formed in 1-(4-azidophenyl)-3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C29H21N5O2, (IIe), but here the dimers are linked into a chain of rings by two independent C—H···π(arene) hydrogen bonds. Comparisons are made between the molecular conformations within both series of compounds. | |
dc.format.extent | 9 | |
dc.language.iso | eng | |
dc.relation.ispartof | Acta Crystallographica Section E Crystallographic Communications | en |
dc.rights | Copyright © 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.subject | Synthesis | en |
dc.subject | Substitued pyrazoles | en |
dc.subject | Chalcones | en |
dc.subject | Crystal structures | en |
dc.subject | Disorder | en |
dc.subject | Molecular conformation | en |
dc.subject | Hydrogen bonding | en |
dc.subject | Supramolecular assembly | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Functionalized 3-(5-ar-yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen-yl)prop-2-en-1-ones : synthetic pathway, and the structures of six examples | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1107/S2056989020005113 | |
dc.description.status | Peer reviewed | en |
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