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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 3
March 20, 1987 

Determination of Reactivity by MO Theory (Part 50). MO Studies on the Gas Phase Pyrolysis of Esters
Ikchoon Lee*, Young Soo Park, Bon-Su Lee
The gas phase pyrolyses of eight esters have been studied by MNDO-MO method. In the ethylformate pyrolysis, α-methylation had a steric releasing effect whereas β-methylation had a steric crowding in the transition state; the latter, however, is over-compensated by a greater electronic repulsion resulting in a net steric releasing effect. Considerations of formal charges and geometrical changes involved in the activation led us to propose a pyrolysis mechanism in which a preequilibrium of acidic proton transfer is followed by the rate-limiting bond polarization of Cα-O bond in a cyclic transition state.
193 - 196
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