Interaction of thiourea and urea with maleimide: comparative theoretical DFT study

A gas-phase mechanism reaction of maleimide with urea or thiourea was studied by DFT method. A comparison between atomic charges, Fukui index evaluation and Frontier orbitals theory was carried out. The involvement of pre- and post-reactive complexes was examined as the reaction profiles are modelle...

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Main Authors:	Nabila Achoui, Karima Zaioua, Dalila Hammoutène, Bellara Kolli-Nedjar, Yamina Akacem
Format:	Article
Language:	English
Published:	Elsevier 2019-09-01
Series:	Heliyon
Subjects:	Organic chemistry Physical chemistry Fukui indices DFT Reaction mechanism Intrinsec reaction coordinate
Online Access:	http://www.sciencedirect.com/science/article/pii/S2405844019359900

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spelling	doaj-8fdeeb4f13e44b938774fac4808a8b672020-11-25T02:56:36ZengElsevierHeliyon2405-84402019-09-0159e02330Interaction of thiourea and urea with maleimide: comparative theoretical DFT studyNabila Achoui0Karima Zaioua1Dalila Hammoutène2Bellara Kolli-Nedjar3Yamina Akacem4USTHB, Faculty of Chemistry, Laboratory of Thermodynamics and Molecular Modeling, BP 32, Al Alia, 16111, Bab Ezzouar, Algiers, Algeria; Corresponding author.USTHB, Faculty of Chemistry, Laboratory of Thermodynamics and Molecular Modeling, BP 32, Al Alia, 16111, Bab Ezzouar, Algiers, AlgeriaUSTHB, Faculty of Chemistry, Laboratory of Thermodynamics and Molecular Modeling, BP 32, Al Alia, 16111, Bab Ezzouar, Algiers, AlgeriaUSTHB, Faculty of Chemistry, Laboratory of Applied Organic Synthesis, BP32, El Alia, 16111, Bab Ezzouar, Algiers, AlgeriaUSTHB, Faculty of Chemistry, Laboratory of Thermodynamics and Molecular Modeling, BP 32, Al Alia, 16111, Bab Ezzouar, Algiers, AlgeriaA gas-phase mechanism reaction of maleimide with urea or thiourea was studied by DFT method. A comparison between atomic charges, Fukui index evaluation and Frontier orbitals theory was carried out. The involvement of pre- and post-reactive complexes was examined as the reaction profiles are modelled. For each mechanism, two approaches have been proposed through nitrogen and sulfur (for thiourea), or oxygen and nitrogen (for urea) attack. The results indicate that the carbon double bonded of maleimide is the electophilic site and chalcogen atom of chalcogenourea is the nucleophilic one. The obtained activation free energies predict suitable specie that could be generated after an opening-cycle and new bonds formation. Consequently, the sulfur attack of thiourea was promoted on oxygen (urea) which is in accordance with the experiments.http://www.sciencedirect.com/science/article/pii/S2405844019359900Organic chemistryPhysical chemistryFukui indicesDFTReaction mechanismIntrinsec reaction coordinate
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Nabila Achoui Karima Zaioua Dalila Hammoutène Bellara Kolli-Nedjar Yamina Akacem
spellingShingle	Nabila Achoui Karima Zaioua Dalila Hammoutène Bellara Kolli-Nedjar Yamina Akacem Interaction of thiourea and urea with maleimide: comparative theoretical DFT study Heliyon Organic chemistry Physical chemistry Fukui indices DFT Reaction mechanism Intrinsec reaction coordinate
author_facet	Nabila Achoui Karima Zaioua Dalila Hammoutène Bellara Kolli-Nedjar Yamina Akacem
author_sort	Nabila Achoui
title	Interaction of thiourea and urea with maleimide: comparative theoretical DFT study
title_short	Interaction of thiourea and urea with maleimide: comparative theoretical DFT study
title_full	Interaction of thiourea and urea with maleimide: comparative theoretical DFT study
title_fullStr	Interaction of thiourea and urea with maleimide: comparative theoretical DFT study
title_full_unstemmed	Interaction of thiourea and urea with maleimide: comparative theoretical DFT study
title_sort	interaction of thiourea and urea with maleimide: comparative theoretical dft study
publisher	Elsevier
series	Heliyon
issn	2405-8440
publishDate	2019-09-01
description	A gas-phase mechanism reaction of maleimide with urea or thiourea was studied by DFT method. A comparison between atomic charges, Fukui index evaluation and Frontier orbitals theory was carried out. The involvement of pre- and post-reactive complexes was examined as the reaction profiles are modelled. For each mechanism, two approaches have been proposed through nitrogen and sulfur (for thiourea), or oxygen and nitrogen (for urea) attack. The results indicate that the carbon double bonded of maleimide is the electophilic site and chalcogen atom of chalcogenourea is the nucleophilic one. The obtained activation free energies predict suitable specie that could be generated after an opening-cycle and new bonds formation. Consequently, the sulfur attack of thiourea was promoted on oxygen (urea) which is in accordance with the experiments.
topic	Organic chemistry Physical chemistry Fukui indices DFT Reaction mechanism Intrinsec reaction coordinate
url	http://www.sciencedirect.com/science/article/pii/S2405844019359900
work_keys_str_mv	AT nabilaachoui interactionofthioureaandureawithmaleimidecomparativetheoreticaldftstudy AT karimazaioua interactionofthioureaandureawithmaleimidecomparativetheoreticaldftstudy AT dalilahammoutene interactionofthioureaandureawithmaleimidecomparativetheoreticaldftstudy AT bellarakollinedjar interactionofthioureaandureawithmaleimidecomparativetheoreticaldftstudy AT yaminaakacem interactionofthioureaandureawithmaleimidecomparativetheoreticaldftstudy
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Interaction of thiourea and urea with maleimide: comparative theoretical DFT study

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