Fragmentation Method For Assigning Oxidation Numbers In Organic And Bioorganic Compounds

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Oxidation number (ON) is taught as an electron-counting concept for redox reactions in chemistry curriculum. The molecular formula method, the Lewis formula method, and the structural formula method have all been used to determine ON. However, the task of assigning ON still poses problems for some teachers and students. This paper explores a new method, the fragmentation method, which is a visual approach for counting the individual ON of any atom according to its structural formula. The critical step is to break the carbon-heteroatom bond into organic fragments and inorganic fragments. The individual ON of carbon atoms and heteroatoms can be determined by the bond cleavages in the organic and biological compounds. The mean ON of carbons can be calculated by the arithmetic mean of all individual ON of carbons in a molecule or molecular ion. The step-by-step operating procedures and examples are provided. When comparing corresponding molecules in organic conversions, the change of individual ON of atoms can be used as a tool for determining the number of transferred electrons. Furthermore, a reaction site can be identified by their changes of individual ON, chemical composition, and bond order in metabolic redox reactions.