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Kinetics and mechanism of the interaction of amines with aryl β‐haloethyl sulphones
Author(s) -
Matvienko Viktor N.,
Perepichka Igor F.,
Popov Anatoly F.,
Piskunova Zhanna P.
Publication year - 1994
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.610071002
Subject(s) - chemistry , kinetic isotope effect , deuterium , aryl , amine gas treating , acetonitrile , kinetics , reaction mechanism , medicinal chemistry , substrate (aquarium) , transition state , computational chemistry , organic chemistry , catalysis , alkyl , physics , oceanography , quantum mechanics , geology
The influence of a number of factors, i.e. amine basicity, substrate structure, temperature and deuterium isotope effect, on the rate of phenyl β‐bromoethyl sulphone and aryl β‐chloroethyl sulphone 1,2‐elimination by reaction with amines in acetonitrile was investigated. On the basis of a comparative analysis of the ρ 0 , β, k H / k D , ΔH‡ and Δ S 25 ‡values obtained with those for the reaction of β‐halopropiophenone 1,2‐elimination, the conclusion was drawn that the E 2 mechanism with an anion‐like transition state occurs for the given substrates under the conditions studied.