Abstract
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.
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