
TY  - JOUR
A1  - McLennan, DJ 
T1  - Model calculations of isotope effects. VIII. Deprotonation of nitroethane
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1983
VL  - 36
IS  - 8
SP  - 1513
EP  - 1520
KW  - 
UR  - https://doi.org/10.1071/CH9831513 
N2  - 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. 
ER  -

