
%0 Journal Article
%A Leahy, GD 
%A Liveris, M 
%A Miller, J 
%A Parker, AJ 
%T The S<sub>N</sub> mechanism in aromatic compounds. XX. The nucleophilicity of phenoxides
%J Australian Journal of Chemistry
%D 1956/09/01
%V 9
%N 3
%P 382-390
%K 
%R https://doi.org/10.1071/CH9560382
%U https://www.publish.csiro.au/paper/CH9560382 
%X The reactions of a series of phenoxides in MeOH with 1-chloro-2,4-dinitrobeneene (and in one case with picryl chloride also) have been measured. They are compared with each other and with the OMe- reaction.   The reactions of the several phenoxides show a relationship between basicity and nucleophilicity analogous to the Bronsted relationship between acid-base strength and catalytic activity, but the relationship does not include OMe-. The phenoxide reactions also obey the Hammett equation with a &#961; value similar to those for ionization of phenols in water and alcohols.   General features of nucleophilicity and basicity are discussed in outline. 
