VAg reactivity indices (ß) measured for naphthalene, anthracene, 1,2-benzanthracene, naphthacene, 1,2,5,6-dibenzanthracene, pentacene, and/or certain derivatives vary by six orders of magnitude in benzene at 25°. An orbital correlation through the transition state is presented for anthracene as a model acceptor in an attempt to identify those acceptor properties which contribute to the activation energy for O^Ag addition insofar as this largely controls acceptor reactivity. It is shown that the x-relocalization energy provides a satisfactory reactivity parameter for unsubstituted acceptors if this is estimated as the difference in x-electron energy of the acceptor and of those odd-alternant fragments which provide electron localization at the site of CVAg addition, with a value of -36 kcal for the bond integral. Electron donating substituents at the site of (VAg addition increase acceptor reactivity in the order H < C6H5 < CH30 ~CH3, each methyl substituent producing an increase in reactivity by a factor of *~13 for anthracene.

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