OH−-induced β-elimination reactions with 1-(2-Xethyl)-4-nitrobenzene substrates in solvent mixture H2O/CH3CN and H2O/DMSO: Reactivity and mechanism

OH−-induced β-elimination reactions with 1-(2-Xethyl)-4-nitrobenzene substrates in solvent... The behaviour of 1-(2-bromoethyl) 4-nitrobenzene (1), N,N,N-triethyl-2-(4-nitrophenyl)ethanaminium bromide (2) and N,N-diethyl-N-[2-(4-nitrophenyl)ethyl]octan-1-aminium bromide (3) in the OH−-induced elimination reactions with formation of 1-nitro-4-vinylbenzene in mixtures of DMSO/H2O or CH3CN/H2O has been investigated. With all three substrates an increase in dipolar aprotic solvent content implies a limited increase of the second-order rate constant k OH up to ≅605, and then an exponential increase is observed. The variation of activation parameters ΔH # and dGS #, measured in DMSO/H2O mixtures, is parallel for 1 and 2. This similar behaviour of 1 and 2 with respect to variation in solvent composition is evidence that it is not possible to use this technique of solvent effect for the mechanistic diagnosis of elimination reactions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

OH−-induced β-elimination reactions with 1-(2-Xethyl)-4-nitrobenzene substrates in solvent mixture H2O/CH3CN and H2O/DMSO: Reactivity and mechanism

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Publisher
Brill Academic Publishers
Copyright
Copyright © 2006 by VSP
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/156856706778938509
Publisher site
See Article on Publisher Site

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