Abstract
A study of the charge distribution in the 1-hydropyrenyl anion (2 - ), and of its regioselectivity toward electrophilic attack was undertaken. In order to obtain reliable information on the reactive positions in 2 - , a model with the same conjugated system was prepared, which has its 1-position fixed with a spirocyclopentane ring. Highly resolved 1 H and 13 C NMR spectra of this spiro[cyclopentane-1,1'-[1H]pyrenyl] anion (1 - ) and of 2 - were obtained. These spectra could be completely assigned by means of COSY, NOESY, and 2D 1 H- 13 C COSY techniques. According to the 13 C NMR measurements, 5-Cof 1 - and 2 - bears the highest negative charge. The results of PM3 semiempirical calculations support this finding, and furthermore, a large HOMO coefficient was calculated at the quaternary 3a-C of 2 - , suggesting that this position is susceptible toward attack by soft electrophiles. In full agreement with the 13 C NMR and PM3 results, 5-C of 1 - and 2 - show the highest reactivity toward electrophilic attack, while the quaternary 3a-C of 1 - and 2 - is attacked by soft electrophiles
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