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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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. |
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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 |
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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. |
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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 |
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2015 |
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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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1681042706646695936 |