Aromatic N1-benzotriazole derivatives represent a class of triazoles extensively studied for their broad use in synthetic applications especially in the area of pharmacology. Interestingly, drugs utilizing the benzotriazole moiety shown utility as antimicrobial, antitumor and cholesterol lowering agents. Although myriad chemical studies have been performed on this system, it is interesting that studies involving N1-substituted derivatives of other annulenotriazole systems have yet to be explored. The only other known compound is the N1-phenylcyclooctatetraenotriazole, which was first synthesized in 1967. However, the chemical properties of this non-aromatic triazole (with respect to the [8]annulene ring) are largely unknown. We have performed a one electron reduction study on this system, as well as that of the fully aromatic N1-phenylbenzotriazole, to determine how the aromatic triazole ring affects electron spin density within the respective fused non-aromatic and aromatic annulene rings. The anion radicals of both compounds were generated by alkali metal reduction and detected using Electron Paramagnetic Resonance (EPR) spectroscopy. Our results reveal considerable differences in the distribution of electron spin. This is largely a consequence of changes in aromaticity upon reduction of these two annulenotriazoles.

Influence of 1,2,3-triazole aromaticity on electron spin distribution in annulenotriazole anion radicals

255th National Meeting (2018)

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