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

被引：3

作者：

Achoui, Nabila ^{[1
]}

Zaioua, Karima ^{[1
]}

Hammoutene, Dalila ^{[1
]}

Kolli-Nedjar, Bellara ^{[2
]}

Akacem, Yamina ^{[1
]}

机构：

[1] USTHB, Fac Chem, Lab Thermodynam & Mol Modeling, BP 32, Algiers 16111, Algeria

[2] USTHB, Fac Chem, Lab Appl Organ Synth, BP32, Algiers, Algeria

来源：

HELIYON | 2019年 / 5卷 / 09期

关键词：

Organic chemistry; Physical chemistry; Fukui indices; DFT; Reaction mechanism; Intrinsec reaction coordinate; Thiourea and urea; DERIVATIVES;

D O I：

10.1016/j.heliyon.2019.e02330

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

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.

引用

页数：9

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