Tautomeric and conformational properties of acetoacetamide: electron diffraction and quantum chemical study

J Org Chem. 2006 Jul 7;71(14):5298-302. doi: 10.1021/jo060603e.

Abstract

The tautomeric properties of acetoacetamide, CH3C(O)CH2C(O)NH2, have been investigated by gas electron diffraction (GED) and quantum chemical calculations (B3LYP and MP2 approximations with 6-31G(d,p) and 6-311++G(3df,pd) basis sets). GED results in a mixture of 63(7)% enol tautomer and 37(7)% diketo form at 74(5) degrees C. Only one enol form with the O-H bond adjacent to the methyl group (CH3C(OH)=CHC(O)NH2) and only one diketo conformer (with dihedral angles tau(O=C(CH3)-C-C) = 31.7(7.5) degrees and tau(O=C(NH2)-C(H2)-C(O)) = 130.9(4.5) degrees ) are present. The calculated tautomeric composition varies in a wide range depending on the quantum chemical method and basis set. Only the B3LYP method with small basis sets reproduces the experimental composition correctly.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetoacetates / chemistry*
  • Amides / chemistry*
  • Electrons
  • Gases / chemistry
  • Hydrogen Bonding
  • Models, Chemical
  • Molecular Conformation
  • Quantum Theory

Substances

  • Acetoacetates
  • Amides
  • Gases