New approach for assigning mean oxidation number of carbons to organonitrogen and organosulfur compounds

Abstract Organonitrogen and organosulfur compounds are abundant in the natural environment. To understand the biological redox pathways properly, it is important for learners to be able to count the oxidation number of organic carbons. However, the process of counting is not always easy. In addition, organonitrogen and organosulfur molecules are seldom studied. To compensate these problems, this paper explores the bond-dividing method, which can effectively determine the mean oxidation number of carbons of organonitrogen and organosulfur molecules. This method uses the cleavage of carbon-sulfur and carbon-nitrogen bonds to obtain the organic and inorganic fragments. The mean oxidation numbers of carbon atoms, nitrogen atoms, and sulfur atoms can be calculated by the molecular formulas of their fragments. Furthermore, when comparing organosulfur or organonitrogen molecules in a redox conversion, the changes of the mean oxidation numbers of carbon atoms, nitrogen atoms, and sulfur atoms can be used as indicators to identify the redox positions and determine the number of transferred electrons.