A PROPOSED INTERPRETATION OF THE DESTABILIZING EFFECT OF HYDROXYL-GROUPS ON NITROAROMATIC MOLECULES Academic Article

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. 1989.

authors

• Seminario, Jorge

published proceedings

• CHEMICAL PHYSICS LETTERS

author list (cited authors)

• POLITZER, P., SEMINARIO, J. M., & BOLDUC, P. R.

citation count

• 48

complete list of authors

• POLITZER, P||SEMINARIO, JM||BOLDUC, PR

publication date

• June 1989

publisher

• Elsevier  Publisher

published in

• CHEMICAL PHYSICS LETTERS  Journal

Digital Object Identifier (DOI)

• 10.1016/0009-2614(89)87371-3

start page

• 463

end page

• 469

volume

• 158

issue

• 5

URL

• http%3A%2F%2Fdx.doi.org%2F10.1016%2F0009-2614%2889%2987371-3