“Tschitschibabin type biradicals”: benzenoid or quinoid?

Abstract

Our findings provide a better understanding of the discrepancies related to the discussion in the literature on the ground state of Tschitschibabin's hydrocarbon. A series of phenylene bridged bisnitroxide molecules were designed and studied for the comparison. The simple theoretical and experimental methodologies have been developed and utilized to understand the singlet biradicaloids which exist in semi-quinoid form and exhibits characteristics of biradicaloid and quinoid form simultaneously.