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Kinetics of the reaction of 2-chloro-3-nitro- and 2-chloro-5-nitropyridines with aryloxide ions in methanol
El-Bardan, Ali A.
, p. 347 - 353 (2007/10/03)
The kinetics of the reaction of 2-chloro-3-nitropyridine (ortho-like) and 2-chloro-5-nitropyridine (para-like) with a series of aryloxide ions were studied in methanol at different temperatures. Plots of ΔH* versus ΔS* for both reactions gave good straight lines with isokinetic temperatures of 168 and 195°C. Good linear relationships were obtained from the plots of log k2 against σ° values with relatively large negative ρ values indicating the formation of Meisenheimer σ-complex intermediates. Plots of log k2 against pKa values gave good straight lines indicating that the reactions show an appreciable degree of bond formation in the transition state. An addition-elimination mechanism is suggested. Copyright
