Elevated Reaction Order of 1,3,5-tri-tert-butylbenzene Bromination as Evidence of a Clustered Polybromide Transition State: a Combined Kinetic and Computational Study

Created: 2018-10-22 14:03

Last modified: 2019-03-23 06:34

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Co-author: Alexander Genaev
Co-author: Andrey Shernyukov
Co-author: Georgy Salnikov
Co-author: Vyacheslav Shubin

Description

Kinetics and mechanism of concurrent bromo-de-protonation and bromo-de-tert-butylation of 1,3,5-tri-tert-butylbenzene at different bromine concentrations were studied experimentally and theoretically. Both reactions have high order in bromine (experimental kinetic orders ~5 and ~7, respectively). According to quantum chemical calculations, such high reaction orders are caused by participation of clustered polybromide anions Br2n-1â in transition states. Bromo-de-tert-butylation has higher order due to its bigger reaction center demanding clusters of extended size.

Members

DOI	Description
10.14469/hpc/4838	5Br2 + 2,4,6-tributylbenzene
10.14469/hpc/4839	3Br2 + 2,4,6-tributylbenzene
10.14469/hpc/4869	NMR Data: Elevated Reaction Order of 1,3,5-tri-tert-butylbenzene Bromination as Evidence of a Clustered Polybromide Transition State: a Combined Kinetic and Computational Study
10.14469/hpc/4906	Kinetic isotope effects: Elevated Reaction Order of 1,3,5-tri-tert-butylbenzene Bromination as Evidence of a Clustered Polybromide Transition State: a Combined Kinetic and Computational Study
10.14469/hpc/4948	FAIR Data table. Elevated Reaction Order of 1,3,5-tri-tert-butylbenzene Bromination as Evidence of a Clustered Polybromide Transition State: a Combined Kinetic and Computational Study

Associated DOIs

Current dataset ...	DOI	Description
References	10.1039/C9OB00607A	Published article: Elevated Reaction Order of 1,3,5-tri-tert-butylbenzene Bromination as Evidence of a Clustered Polybromide Transition State: a Combined Kinetic and Computational Study

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