Pyridine reactivity indices

Using their CNDO results Helland and Skancke calculated indices of reactivity (frontier electron density, FED, for electrophilic substitution frontier orbital density, FOD, for nucleophilic substitution frontier radical density, FRD, for radical substitution) for the thienopyridines. It was indicated that the FED index has its highest value for C-3 in the [2,3-]- and 3,2- -fused systems and for C-2 in the [3,4-1-fused isomers. As far as the former group is concerned, the predictions are in agreement with experimental observations (see Section IV,A.). Little experimental evidence is available for the [3,4-]-fused systems, but it seems highly probable that they would have a considerable tendency to undergo addition reactions at the 1,3-positions, since the product would contain a normal rather than a quinoid pyridine ring [Eq. (23)]. 

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