Abstract
Azo coupling reactions of 1-aminonaphthalene with naphthalene-1-diazonium and 4-sulfobenzene-diazonium cations are studied by quantum chemistry. It is found that the reactions are orbital controlled and their regioselectivity is unambiguously governed by the thermodynamic properties of the intermediate σ-complexes and by the effect of the aqueous medium. The latter causes high site selectivity, providing the choice of one of the two possible reaction channels predicted on the basis of quantum-chemical calculations of the isolated molecular systems. As a result, azo coupling occurs at the 4-position of the 1-aminonaphthalene molecule. Additionally, the aqueous medium provides the selection of analytical forms, namely, the protonated azo coupling products that have the quinone-hydrazone structure. On the basis of the quantum-chemical study, the analytical performances of the two azo coupling reactions mentioned above are discussed.
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