5-(2-Naphthyl)thio-1-phenyltetrazole: Chemical Reactivity and Electronic Effects of Conjugation through Sulfur

The title compound, C₁₇H₁₂N₄S, is a sulfide in which an aromatic naphthyl group is connected through the S atom to the electronegative 1-phenyltetrazole. Investigations of similar systems in which oxygen ethers of phenols or naphthols are connected to the very electronegative benzisothiazole 1,1-dioxide have found that the O atom of the central ether linkage has one long bond to the aryl group of the original phenol or naphthol and one short bond to the heterocyclic system. The C-O bond lengths show that the O atom is strongly conjugated to the heterocycle but not at all to the aryl ring. In the title compound with its thioether (sulfide) in place of an oxygen ether, the difference in the two central C-S bond lengths is very small and the S atom is only slightly conjugated with either of the two aromatic systems to which it is attached. These differences between the oxygen and sulfur ethers are reflected in their chemical reactivity.

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