A B S T R A C T  
This thesis presents rate data for the hydrolysis 
of o-, m- and p-substituted benzamides and phenylacetam­
ides in both acid and base at 65.6°C and 86°C. Chemical 
shift data for the side chain protons of similarly subs­
tituted phenylacetamides and benzhydrazides, the latter 
serving as model compounds for the benzamides, are also 
presented. 
The hydrolysis rates of the m- and p-substituted 
amides in both acid and base were well correlated by the 
Hammett cr constants. The significance of the p va lues 
obtained (in the phenylacetamide and benzamide series) 
is discussed in terms of the relative kinetic importance 
of steps one and two of the accepted simple two-step 
mechanism for amide hydrolysis. 
The ortho rates are shown to be dependent on both 
inductive and steric effects and suggestions are made as 
to the nature of the steric and inductive effects that 
are operating. 
The chemical shifts of the -CH29 ~"NH and -NH2 pro­
tons of the m- and p-substituted phenylacetamides and 
benzhydrazides all gave excellent correlations with the 
Hammett O constants. It is concluded that the effect of 
non-ortho ring substituents on the side chain in these 
amide systems, both in the ground state and in chemical 
reactions, is mainly an inductive one. 
The -NH proton chemical shifts of the o-benzhydra-
zides are shown to be dependent on purely electrical 
effects while the -Ni^ chemical shifts are dependent on 
inductive and steric effects. This finding, strange at 
first glance, is explained. 
The methylene proton chemical shifts of the o-
phenylacetamides seem to be dependent on both electrical 
and steric factors.