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Theoretical study on the effective dehydrochlorination of 1,2-dichloroethane catalyzed by tetraalkylphosphonium chlorides: electrostatically controlled reactivity

Abstract

This work aims at understanding the intriguing experimental observation of the most effective dehydrochlorination of 1,2-dichloroethane (DCE) catalyzed by tetrabutylphosphonium chloride (C4444P+Cl−) vs. other tetraalkylphosphonium chlorides, imidazolium chlorides, and inorganic molten salts. The calculation on the C4444P+Cl−-catalyzed DCE dehydrochlorination reaction shows a bimolecular elimination (E2) mechanism, where the ionic liquid (IL) plays an amphiphilic dual activation role, whose component anion and cation act cooperatively to induce the cleavage of C−H and C−Cl bonds of DCE and the formation of H−Cl bond. The effective dehydrochlorination of DCE catalyzed by C4444P+Cl− IL is attributed to the strongest basicity of the IL, which originates from the weakest electrostatic interaction between the anionic and cationic partners in comparison with other tetraalkylphosphonium chlorides, imidazolium chlorides, and inorganic molten salts. The theoretical calculations emphasize the electrostatically controlled character of DCE dehydrochlorination in ILs as well as the cooperative catalysis of ILs. The present results would provide guidance for understanding the reactivity of IL-catalyzed dehydrochlorination of DCE.

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Publication details

The article was received on 20 Jan 2018, accepted on 28 Apr 2018 and first published on 01 May 2018


Article type: Paper
DOI: 10.1039/C8NJ00354H
Citation: New J. Chem., 2018, Accepted Manuscript
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    Theoretical study on the effective dehydrochlorination of 1,2-dichloroethane catalyzed by tetraalkylphosphonium chlorides: electrostatically controlled reactivity

    X. Mu, Y. Jing, C. Liu and D. Zhang, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ00354H

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