Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products

Mohammed A. E. Shaibah; Hemmige S. Yathirajan; Asma .; Nagaraja Manju; Balakrishna Kalluraya; Ravindranath S. Rathore; Christopher Glidewell

doi:10.1107/S2056989020001735

Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products

Mohammed A. E. Shaibah, Hemmige S. Yathirajan, Asma ., Nagaraja Manju, Balakrishna Kalluraya, Ravindranath S. Rathore, Christopher Glidewell

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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—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.

Original language	English
Pages (from-to)	360-365
Number of pages	6
Journal	Acta Crystallographica Section E
Volume	76
Issue number	3
Early online date	14 Feb 2020
DOIs	https://doi.org/10.1107/S2056989020001735
Publication status	Published - Mar 2020

Keywords

Synthesis
Cyclocondensation
Chalcones
Heterocyclic compounds
Reduced pyrazoles
Crystal structures
Molecular conformation
Hydrogen bonding
Supramolecular assembly

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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.
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Cite this

@article{a65be6d7ada94ca7b41802f60bdff105,

title = "Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products",

abstract = "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—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.",

keywords = "Synthesis, Cyclocondensation, Chalcones, Heterocyclic compounds, Reduced pyrazoles, Crystal structures, Molecular conformation, Hydrogen bonding, Supramolecular assembly",

author = "Shaibah, \{Mohammed A. E.\} and Yathirajan, \{Hemmige S.\} and Asma . and Nagaraja Manju and Balakrishna Kalluraya and Rathore, \{Ravindranath S.\} and Christopher Glidewell",

note = "HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.",

year = "2020",

month = mar,

doi = "10.1107/S2056989020001735",

language = "English",

volume = "76",

pages = "360--365",

journal = "Acta Crystallographica Section E",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "3",

}

TY - JOUR

T1 - Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products

AU - Shaibah, Mohammed A. E.

AU - Yathirajan, Hemmige S.

AU - ., Asma

AU - Manju, Nagaraja

AU - Kalluraya, Balakrishna

AU - Rathore, Ravindranath S.

AU - Glidewell, Christopher

N1 - HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.

PY - 2020/3

Y1 - 2020/3

N2 - 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—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.

AB - 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—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.

KW - Synthesis

KW - Cyclocondensation

KW - Chalcones

KW - Heterocyclic compounds

KW - Reduced pyrazoles

KW - Crystal structures

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

UR - https://www.scopus.com/pages/publications/85081717316

U2 - 10.1107/S2056989020001735

DO - 10.1107/S2056989020001735

M3 - Article

SN - 2056-9890

VL - 76

SP - 360

EP - 365

JO - Acta Crystallographica Section E

JF - Acta Crystallographica Section E

IS - 3

ER -

Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products

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Keywords

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