14diazabenzene

14Diazabenzene, also known as 1,4-diazacyclohexa-2,5-diene or more commonly as para-benzoquinone diimine, is an organic compound with the chemical formula C6H6N2. It is a heterocyclic aromatic compound, structurally related to benzene where two carbon atoms are replaced by nitrogen atoms in a 1,4 arrangement. This arrangement results in a six-membered ring containing two nitrogen atoms and four carbon atoms, with alternating double bonds.

Para-benzoquinone diimine is a relatively unstable compound and readily undergoes oxidation or reduction reactions. It can exist in different tautomeric forms. Its synthesis typically involves the oxidation of p-phenylenediamine. Due to its reactivity, it is often used as an intermediate in the synthesis of other organic molecules, particularly in the preparation of dyes and pharmaceuticals. It has also been studied for its electrochemical properties and its role in certain biological processes. The compound's diimine structure contributes to its electron-deficient nature, making it susceptible to nucleophilic attack. Its precise physical and chemical properties are often dependent on the specific reaction conditions and the presence of other substances.