TY - JOUR
T1 - Condensation mechanism of cage hexabenzylhexaazaisowurtzitane from glyoxal and benzylamine
T2 - A computational study
AU - Dong, Kai
AU - Sun, Cheng Hui
AU - Zhang, Shao Wen
AU - Wang, Hui Yun
AU - Song, Jian Wei
AU - Pang, Si Ping
N1 - Publisher Copyright:
© 2017 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
PY - 2017
Y1 - 2017
N2 - 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-1 and 60.49 kcal mol-1. The acid-catalyzed water elimination reaction of 1,2-bis(benzylamino)-1,2-ethanediol decreases to 17.17 kcal mol-1, 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.
AB - 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-1 and 60.49 kcal mol-1. The acid-catalyzed water elimination reaction of 1,2-bis(benzylamino)-1,2-ethanediol decreases to 17.17 kcal mol-1, 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.
UR - http://www.scopus.com/inward/record.url?scp=85032572311&partnerID=8YFLogxK
U2 - 10.1039/c7nj00972k
DO - 10.1039/c7nj00972k
M3 - Article
AN - SCOPUS:85032572311
SN - 1144-0546
VL - 41
SP - 12694
EP - 12699
JO - New Journal of Chemistry
JF - New Journal of Chemistry
IS - 21
ER -