Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical

The compound (E)-4-Hydroxy-3-methyl-N'-(thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide (C15H13N4O2S) is a stable free radical quinoxaline derivative. It was prepared by treatment of an acidified ethanolic solution of 3-methyl-2-(thiophen-2-ylmethylenehydrazinocarbonyl)quinoxali...

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Main Authors: Ibrahim, Mohammad M., Al-Refai, Mahmoud, Dawoud, Jamal N., Abu-El-Halawa, Rajab, Massad, Mohannad H., Judeh, Zaher, Ali, Basem F.
Other Authors: School of Chemical and Biomedical Engineering
Format: Article
Language:English
Published: 2015
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Online Access:https://hdl.handle.net/10356/106579
http://hdl.handle.net/10220/25020
http://www.asianjournalofchemistry.co.in/user/journal/viewarticle.aspx?ArticleID=24_7_21
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spelling sg-ntu-dr.10356-1065792019-12-06T22:14:29Z Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical Ibrahim, Mohammad M. Al-Refai, Mahmoud Dawoud, Jamal N. Abu-El-Halawa, Rajab Massad, Mohannad H. Judeh, Zaher Ali, Basem F. School of Chemical and Biomedical Engineering DRNTU::Science::Medicine::Biomedical engineering DRNTU::Science::Chemistry::Biochemistry The compound (E)-4-Hydroxy-3-methyl-N'-(thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide (C15H13N4O2S) is a stable free radical quinoxaline derivative. It was prepared by treatment of an acidified ethanolic solution of 3-methyl-2-(thiophen-2-ylmethylenehydrazinocarbonyl)quinoxaline-4-oxide with a solution of CuSO4.5H2O. The crystal structure shows that the molecule contains non-planar linking unit between quinoxaline and thiophene rings. Hydrogen bonding (N-H…O), π…π stacking and S…S intermolecular interactions may be effective in the stabilization of the crystal lattice. Density functional theory results agree well with X-ray experimental findings indicating that the free radical is indeed possible and that the stability of this compound might be attributed to the highly electron delocalization of the conjugation system over the whole compound along with the extra stabilization from the intramolecular interactions. 2015-02-06T02:35:43Z 2019-12-06T22:14:29Z 2015-02-06T02:35:43Z 2019-12-06T22:14:29Z 2012 2012 Journal Article Ibrahim, M. M., Al-Refai, M., Dawoud, J. N., Abu-El-Halawa, R., Massad, M. H., Judeh, Z., et al (2012). Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical. Asian journal of chemistry, 24(7), 2926-2930. 0970-7077 https://hdl.handle.net/10356/106579 http://hdl.handle.net/10220/25020 http://www.asianjournalofchemistry.co.in/user/journal/viewarticle.aspx?ArticleID=24_7_21 en Asian journal of chemistry © 2012 Asian Journal of Chemistry.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Medicine::Biomedical engineering
DRNTU::Science::Chemistry::Biochemistry
spellingShingle DRNTU::Science::Medicine::Biomedical engineering
DRNTU::Science::Chemistry::Biochemistry
Ibrahim, Mohammad M.
Al-Refai, Mahmoud
Dawoud, Jamal N.
Abu-El-Halawa, Rajab
Massad, Mohannad H.
Judeh, Zaher
Ali, Basem F.
Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical
description The compound (E)-4-Hydroxy-3-methyl-N'-(thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide (C15H13N4O2S) is a stable free radical quinoxaline derivative. It was prepared by treatment of an acidified ethanolic solution of 3-methyl-2-(thiophen-2-ylmethylenehydrazinocarbonyl)quinoxaline-4-oxide with a solution of CuSO4.5H2O. The crystal structure shows that the molecule contains non-planar linking unit between quinoxaline and thiophene rings. Hydrogen bonding (N-H…O), π…π stacking and S…S intermolecular interactions may be effective in the stabilization of the crystal lattice. Density functional theory results agree well with X-ray experimental findings indicating that the free radical is indeed possible and that the stability of this compound might be attributed to the highly electron delocalization of the conjugation system over the whole compound along with the extra stabilization from the intramolecular interactions.
author2 School of Chemical and Biomedical Engineering
author_facet School of Chemical and Biomedical Engineering
Ibrahim, Mohammad M.
Al-Refai, Mahmoud
Dawoud, Jamal N.
Abu-El-Halawa, Rajab
Massad, Mohannad H.
Judeh, Zaher
Ali, Basem F.
format Article
author Ibrahim, Mohammad M.
Al-Refai, Mahmoud
Dawoud, Jamal N.
Abu-El-Halawa, Rajab
Massad, Mohannad H.
Judeh, Zaher
Ali, Basem F.
author_sort Ibrahim, Mohammad M.
title Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical
title_short Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical
title_full Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical
title_fullStr Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical
title_full_unstemmed Crystal structure and density functional calculation of (E)-4-Hydroxy-3-methyl-N'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical
title_sort crystal structure and density functional calculation of (e)-4-hydroxy-3-methyl-n'- (thiophen-2-ylmethylene)-1,4-dihydroquinoxaline-2-carbohydrazide radical
publishDate 2015
url https://hdl.handle.net/10356/106579
http://hdl.handle.net/10220/25020
http://www.asianjournalofchemistry.co.in/user/journal/viewarticle.aspx?ArticleID=24_7_21
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