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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Model calculations of isotope effects. VIII. Deprotonation of nitroethane

DJ McLennan

Australian Journal of Chemistry 36(8) 1513 - 1520
Published: 1983

Abstract

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 α-deuterium isotope effect comparison disqualifies from consideration those transition states in which rehybridization of Cα and delocalization of the partial negative charge by the nitro group keep pace with the extent of deprotonation. Transition-state models wherein Cα is carbanionic and essentially pyramidal yield theoretical isotope effects lying within the experimental range.

https://doi.org/10.1071/CH9831513

© CSIRO 1983

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