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Condensation Mechanism of Cage Hexabenzylhexaazaisowurtzitane from Glyoxal and Benzylamine: A Computational Study

Abstract

A computational study was performed on the condensation mechanism for the formation of cage hexabenzylhexaazaisowurtzitane (HBIW) from glyoxal and benzylamine. The results suggest that the intermediate 1,2-bis(benzylamino)-1,2-ethanediol is present in the reaction system, especially in the presence of acid catalyst. However, it is unfavorable for N,N'-dibenzyl-1,2-ethanediimine to be formed without the use of acid because the energy barriers for elimination of two water molecules from 1,2-bis(benzylamino)-1,2-ethanediol are 51.99 kcal/mol and 60.49 kcal/mol. The acid-catalyzed water elimination reaction of 1,2-bis(benzylamino)-1,2-ethanediol decreases to 17.17 kcal/mol, resulting in the formation of another intermediate of 1-(benzylamino)-2-(benzylimino)-ethanol. The 1-(benzylamino)-2-(benzylimino)-ethanol reacts with another 1,2-bis(benzylamino)-1,2-ethanediol to provide HBIW through four cyclization reactions.

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Publication details

The article was received on 24 Mar 2017, accepted on 04 Sep 2017 and first published on 04 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ00972K
Citation: New J. Chem., 2017, Accepted Manuscript
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    Condensation Mechanism of Cage Hexabenzylhexaazaisowurtzitane from Glyoxal and Benzylamine: A Computational Study

    K. Dong, C. Sun, S. Zhang, H. Wang, J. Song and S. Pang, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ00972K

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