Nitro ⇌ aci-Nitro Tautomerism

Koop Lammertsma, Bharatam V. Prasad

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66 Citations (Scopus)


The nitromethane ⇌ aci-nitromethane tautomerism is studied by high-level ab initio methods. The MP2/6-31G* geometry of nitromethane compares well with that determined experimentally. The G1 energy difference between the two tautomers amounts to 14.1 kcal/mol in favor of nitromethane. The calculated heat of atomization of −570.7 kcal/mol for nitromethane differs by only 2.4 kcal/mol from the experimental value. The nitromethide anion has Cs symmetry with the 6-311+G* basis set. Its G1 proton affinity is 355.2 kcal/mol, which differs from the gas-phase value by 1.4 kcal/mol. The anion does not display Y-aromaticity.

Original languageEnglish
Pages (from-to)2348-2351
Number of pages4
JournalJournal of the American Chemical Society
Issue number6
Publication statusPublished - 1 Mar 1993
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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