Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products
Chalcones 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, C18H13Cl...
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doaj-a72049833822454ab391c04fa563fc7f2020-11-25T02:00:09ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-03-0176336036510.1107/S2056989020001735zl2770Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three productsMohammed A. E. Shaibah0Hemmige S. Yathirajan1Asma2Nagaraja Manju3Balakrishna Kalluraya4Ravindranath S. Rathore5Christopher Glidewell6Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574 199, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574 199, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574 199, IndiaDepartment of Bioinformatics, School of Earth, Biological and Environmental Sciences, Central University of South Bihar, Gaya-824236, IndiaSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UKChalcones 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—H...π(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.http://scripts.iucr.org/cgi-bin/paper?S2056989020001735synthesiscyclocondensationchalconesheterocyclic compoundsreduced pyrazolescrystal structuresmolecular conformationhydrogen bondingsupramolecular assembly |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Mohammed A. E. Shaibah Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell |
spellingShingle |
Mohammed A. E. Shaibah Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products Acta Crystallographica Section E: Crystallographic Communications synthesis cyclocondensation chalcones heterocyclic compounds reduced pyrazoles crystal structures molecular conformation hydrogen bonding supramolecular assembly |
author_facet |
Mohammed A. E. Shaibah Hemmige S. Yathirajan Asma Nagaraja Manju Balakrishna Kalluraya Ravindranath S. Rathore Christopher Glidewell |
author_sort |
Mohammed A. E. Shaibah |
title |
Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products |
title_short |
Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products |
title_full |
Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products |
title_fullStr |
Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products |
title_full_unstemmed |
Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products |
title_sort |
conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2020-03-01 |
description |
Chalcones 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—H...π(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. |
topic |
synthesis cyclocondensation chalcones heterocyclic compounds reduced pyrazoles crystal structures molecular conformation hydrogen bonding supramolecular assembly |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989020001735 |
work_keys_str_mv |
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