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Esters of Nitric Acid as Electron Acceptors

It is well known that C-nitro compounds are strong electron acceptors forming readily charge transfer complexes. Nothing so far has been known as regards possible electron accepting properties of Onitro compounds. However, in a series of papers one of us [1—5] and his co-worker [6] have found using the thermal analysis method that nitric esters such as D-mannitol hexanitrate and erythritol tetranitrate can form additive compounds with some aromatic nitro compounds. The problem arose what is the nature of such additive compounds: whether they are charge transfer complexes, and which of the components is the electron acceptor. A suggestion was advanced that nitric esters can act as electron acceptors and this was substantiated by our present work. We examined now an interaction between nitric esters of mono-, di-, tri-, tetraand hexahydroxylic alcohols and a model electron donor — tetramethyl-p-phenylenediamine (TMPD). The choice of the latter was justified by its low ionisation potential (6.5 eV). The preliminary report has already been published [7]. We found that the solutions of nitric esters, when added to a solution of T M P D , produce an intense violet colour. This colour is due to two absorption bands: at 570 and 620 nm (Fig. 1). Their source is the T M P D cation ("Wurster radical") (I) [8] formed from T M P D through the loss of one electron.