ACIDITY AND DELOCALIZATION OF C-70-SUBSTITUTED HYDROFULLERENES - AN AB-INITIO QUANTUM-CHEMICAL STUDY

An ab initio HF/3-21G study is made of the acidity of a series of subs tituted [70]hydrofullerenes. All systems under consideration result fr om substituting one hydrogen atom in C70H2 by a functional group, for which a series of alkyl and fluorine- and chlorine-containing groups h as been chosen. Acidities are obtained via a previously set up correla tion with calculated gas-phase deprotonation energies. Electronic delo calisation in the conjugate base is seen to play an important role in the fairly high acidity of these systems. Also, the interplay of group hardness and electronegativity on the acidity sequence is shown. (C) 1998 Elsevier Science B.V. All rights reserved.