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- W2029489752 abstract "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." @default.
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- W2029489752 date "1989-06-01" @default.
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- W2029489752 title "A proposed interpretation of the destabilizing effect of hydroxyl groups on nitroaromatic molecules" @default.
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- W2029489752 doi "https://doi.org/10.1016/0009-2614(89)87371-3" @default.
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