A proposed interpretation of the destabilizing effect of hydroxyl groups on nitroaromatic molecules
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Whereas an amino group stabilizes nitroaromatic molecules toward shock and impact, presumably through a resonance interaction that strengthens the CNO2 bonds, hydroxyl substituents have a sensitizing effect despite having resonance capabilities. This may reflect the formation, by hydroxyaromatics, of the unstable nitronic acid tautomer. A computational analysis (SCF, 3-21G) of the o-nitrophenol system, used as a model, shows that transfer of the phenolic proton to the nitro group produces an equilibrium nitronic acid structure, with a calculated energy 15.4 kcal/mol above o-nitrophenol. Such proton transfer might result from vibrational excitation of the OH bond produced by shock or impact. No analogous equilibrium structure is found for a possible nitronic acid tautomer of o-nitroaniline. 1989.
author list (cited authors)
Politzer, P., Seminario, J. M., & Bolduc, P. R.
complete list of authors
Politzer, Peter||Seminario, Jorge M||Bolduc, Paul R