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Production mechanism of active species on the oxidative bromination following perhydrolase activity
Author(s) -
China Hideyasu,
Okada Yutaka,
Ogino Hiroyasu
Publication year - 2016
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3490
Subject(s) - chemistry , halogenation , peracetic acid , bromine , decarboxylation , hydrogen peroxide , acetic acid , reaction mechanism , organic chemistry , protonation , medicinal chemistry , catalysis , ion
Hypobromous acid and molecular bromine have been described as the active species involved in the oxidative bromination using perhydrolase, which catalyzes the reaction from acetic acid and hydrogen peroxide to peracetic acid (AcOOH). However, the brominating activity of them in a chemical model system was lower than that of the active species produced by the spontaneous reaction between AcOOH and Br − . Consequently, acetyl hypobromite (AcOBr) was suggested as new active species on the bromination by detection of the decarboxylation in the reaction between AcOOH and Br − and the strong brominating power with some tolerance against H 2 O 2 . Its production mechanism was explained as the ionic reaction involving the protonated intermediate of AcOOH by kinetic analysis. Copyright © 2015 John Wiley & Sons, Ltd.