Abstract
Abstractmagnified imageThis study was performed in order to explain different orientation in the reaction of quinolinyl sulfides with nitrating mixture, which converted on one hand quinolinyl sulfides 1, 3 and 5 to sulfoxides 2, 4 and 8, respectively, on the other hand, sulfides 6, 7 to the respective nitroderivatives 9 and 10. Competitive experiments showed following reactivity order: thianthrene 11 ≥ thianthrene 5‐oxide 12 ≥ isothioquinanthrene 3 ≥ thioquinanthrene 1 ≥ 3,3′‐diquinolinyl sulfide 5 ≥ 3,4′‐diquinolinyl sulfide 6 ≥ 4,4′‐diquinolinyl sulfide 7. Considering that NO2+ (as reactive form of nitrating mixture) attacks the most electronodonating (sulfur or carbon) center the reactivity order well correlates with the results of HOMO as well as MEP calculations.
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