
%0 Journal Article
%A McLennan, DJ 
%T Model calculations of isotope effects. VIII. Deprotonation of nitroethane
%J Australian Journal of Chemistry
%D 1983/08/01
%V 36
%N 8
%P 1513-1520
%K 
%R https://doi.org/10.1071/CH9831513
%U https://www.publish.csiro.au/paper/CH9831513 
%X Transition-state models for the base-promoted deprotonation of nitroethane have been designed, and primary and secondary hydrogen-deuterium kinetic isotope effects have been calculated. Comparison of the results with experimental values of the primary isotope effects allows no firm conclusions to be reached concerning probable transition-state structures. However, the secondary &#945;-deuterium isotope effect comparison disqualifies from consideration those transition states in which rehybridization of C&#945; and delocalization of the partial negative charge by the nitro group keep pace with the extent of deprotonation. Transition-state models wherein C&#945; is carbanionic and essentially pyramidal yield theoretical isotope effects lying within the experimental range. 
