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Local energy minima correspond to isomeric 6protonated pyrroles, whose stability has been computed and found to decrease in the a, > aa > oN order. The energy gaps between the minima are in satisfactory agreement with other semiempirical calculations of the localization energies of protonated pyrroles (Fig. 9). Analysis of the energy profile (Fig. 11) linking the local minima (a complexes) indicates that hydrogenbridged structures correspond to energy saddle points, representing the activation barriers for hydrogen shifts in the protonated pyrrole intermediates.

I Introduction A fundamental understanding of structure-reactivity and structureenergy correlations in heteroaromatic compounds is of central importance in chemistry and biochemistry. The classical approach to this subject normally 25 . Copyright 0 1986 by Academic Press Inc. All rights of reproduction in any form reserved. 26 M. SPERANZA [Sec. I involves dissolving the heteroaromatic compound in a liquid medium, where a given reactant is added or generated. A reaction takes place whose rate or equilibria parameters are measured by means of the conventional techniques of physical organic chemistry.

CND0/2 (solid lines) and MINDOj2 (broken lines) calculations of the energy levels of protonated pyrrole (80JPR147). Sec. A] REACTIVITY OF HETEROAROMATIC COMPOUNDS 53 (77TL3565; 80JPR 147). Local energy minima correspond to isomeric 6protonated pyrroles, whose stability has been computed and found to decrease in the a, > aa > oN order. The energy gaps between the minima are in satisfactory agreement with other semiempirical calculations of the localization energies of protonated pyrroles (Fig. 9).

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