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Sulfonation of the Naphthalene Derivatives in Protic Solvent. Principles of Isomer Distribution

Brzezińska E., Kusztal D.

Polish Journal of Chemistry

2002

Vol. 76 / nr 7

975-981

The principles of formation of mono- and disulfonation products of selected derivatives of naphthalene in protic solvents were studied. The position of electrophilic substitution was compared with: localization energies (L+) of the parent compounds; steric effect of methoxy groups; partial charges on carbon atoms in aromatic ring; dipole moment (_) and the binding energies of the products (D). These results suggest that only steric hindrance and the binding energy of the sulfonation products of naphthalene derivatives in protic solvents may be a good prognostic index for isomer distribution substitution products.