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Related Experiment Videos

Formaldehyde oxime <--> nitrosomethane tautomerism.

J A Long1, N J Harris, K Lammertsma

  • 1Department of Chemistry, Faculty of Sciences, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.

The Journal of Organic Chemistry
|October 2, 2001
PubMed
Summary

Formaldehyde oxime is more stable than its tautomer, nitrosomethane, by 15.8 kcal/mol, considering aqueous solvation. This study also details the stability and ionization energies of related nitrone isomers.

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Area of Science:

  • Computational Chemistry
  • Theoretical Chemistry
  • Quantum Chemistry

Background:

  • Tautomerism is a fundamental chemical process involving the interconversion of isomers.
  • Understanding the relative stability of tautomers is crucial for predicting chemical reactivity and properties.
  • Formaldehyde oxime and nitrosomethane represent a specific tautomeric system with potential applications.

Purpose of the Study:

  • To investigate the formaldehyde oxime <--> nitrosomethane tautomerism using advanced computational methods.
  • To compare the stability and properties of formaldehyde oxime, nitrosomethane, and their isomeric nitrone.
  • To assess the influence of solvent effects, including hydrogen bonding, on tautomeric stability.

Main Methods:

  • Utilized Gaussian-2 (G2) theory with MP2(full)/6-31G geometries.

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  • Employed density functional theory (DFT) with B3LYP/6-311+G** functional.
  • Applied self-consistent isodensity polarizable continuum model (SCIPCM) for solvent effects, including explicit water molecules.

    • Main Results:

    • Formaldehyde oxime is predicted to be 15.8 kcal/mol more stable than nitrosomethane with aqueous solvation correction.
    • Unsolvated formaldehyde oxime is 11.1 kcal/mol more stable than the nitrone isomer.
    • Calculated gas-phase ionization energies are provided for all studied species.

    Conclusions:

    • Formaldehyde oxime is the more stable tautomer under aqueous conditions.
    • The computational methods employed provide reliable predictions for tautomeric stability and ionization energies.
    • The study offers insights into the fundamental chemical behavior of formaldehyde oxime and related compounds.