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The results of the prognostic computer synthesis of meso-phenylporphyrins Н2Р(Ph)n sulfo derivatives, which demonstrate the supramolecular nature of the porphyrins sulfonation regioselectivity in concentrated sulfuric acid and oleum, are presented. By means of DFT calculation it has been shown that regioselectivity of meso-phenylporphyrins sulfonation is due to host-guest complex formation of the diprotonated porphyrin platform with two hydrosulfate anions, [H4P(Ph)n](HSO4)2. The guest anions control the reactivity of H4P(Ph)n. First, they activate H4P(Ph)n for electrophilic substitution by partial negative charge transfer to the diprotonated porphyrin. Second, the guest anions are the cause of a total charges redistribution on the carbon atoms of H4P and the phenyl rings, thereby providing the regioselectivity of H4P(Ph)n sulfonation. The data from prognostic stage calculations and method of organic synthesis were used to obtain the new 5,10,15-tris(4’-sulfophenyl)porphine. The obtained results are comprehensive and applicable to other SEAr reactions of porphyrins.

Supramolecular Regioselectivity of meso-Phenylporphyrin Sulfonation. Synthesis of 5,10,15-Tris(4’-sulfophenyl)porphine