Rates of reaction of several 3and 4-substituted benzylamines with 1 -chloro-2,4-dinitrobenzene in azeotropic ethanol at 45' and with toluene-p-sulphonyl chloride in benzene at 45' have been measured.WE recently reported the dissociation constants of substituted benzy1arnines.l Like the dissociation reaction, the reactions studied in the present work, viz., reaction with l-chloro-2,4-dinitrobenzene and with toluene-9-sulphonyl chloride, were expected to lead to substituent constants (6) in good agreement with Taft's 6 ' values which measure the inductive effect of substituted phenyl group^.^
EXPERIMENTALBenzyZumines.-3-Cyanobenzylamine, b. p. 112"/0-5 mm., was prepared by reaction of 3-cyanobenzyl bromide with anhydrous ammonia in an autoclave at 24". The hydrochloride had m. p. 221" (lit.,3 222"). Preparation and physical constants of the other benzylamines have been described previous1y.l
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