
%0 Journal Article
%A Bolton, PD 
%A Jackson, GL 
%T Hydrolysis of amides. IV. Dilute acid hydrolysis of amides of the type R<sub>2</sub>CH-CONH<sub>2</sub> and R<sub>3</sub>C-CONH<sub>2</sub>
%J Australian Journal of Chemistry
%D 1971/03/01
%V 24
%N 3
%P 471-477
%K 
%R https://doi.org/10.1071/CH9710471
%U https://www.publish.csiro.au/paper/CH9710471 
%X Enthalpies and entropies of activation have been derived from rate constants measured over a range of temperature for the dilute acid hydrolysis of isobutyramide, diethylacetamide, &#945;-methylbutyramide, cyclohexaneoarboxamide, cyclopentane-carboxamide, and trimethylacetamide.     These data, in combination with data for other amides produced earlier, show the hydrolysis rate constants to be dominated by steric influences but with a perturbing effect which is proportional to the number of &#945;-hydrogens present in the substituent. The &quot;&#945;-hydrogen bonding&quot; concept of hyperconjugation appears to offer a reasonable explanation of these perturbations.     Controlled steric changes are shown to be non-additive for this reaction and to exert their influence primarily through the enthalpy component of the observed free energy changes. 
