Abstract
The reaction rates of 4-X-2,6-dinitrochlorobenzenes (X = <TEX>$NO_2$</TEX>, CN, <TEX>$CF_3$</TEX>) with Y-substituted benzylamines (Y = p-<TEX>$OCH_3$</TEX>, p-<TEX>$CH_3$</TEX>, H, p-Cl) in MeOH-MeCN mixtures were measured by conductometry at <TEX>$25^{\circ}C$</TEX>. It was observed that the rate constant increased in the order of X = <TEX>$NO_2$</TEX> > CN > <TEX>$CF_3$</TEX> and in the order of Y = p-<TEX>$OCH_3$</TEX> > p-<TEX>$CH_3$</TEX> > H > p-Cl. When the solvent composition was varied, the rate constant increased in the order of 100% MeOH < 50% (v/v) MeOH-MeCN < 100% MeCN. These results may be ascribed to the formation of hydrogen bonds between the alcoholic hydrogen and nitrogen of benzylamines in groud state (GS). We conclude that the reaction takes place via <TEX>$S_NAr$</TEX> base on the transition state parameters <TEX>${\rho}x$</TEX>, <TEX>${\rho}Y$</TEX>, <TEX>$\beta_{nuc}$</TEX>, and solvent effects.
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