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Title: Strength of the N-HiiiO=C and C-HiiiO=C Bonds in Formamide and N-Methylacetamide Dimers

Journal Article · · Journal of Physical Chemistry A
DOI:https://doi.org/10.1021/jp003888m· OSTI ID:15004989
 [1];  [2];  [3];  [4];  [5];  [5]
  1. Pacific Northwest National Laboratory
  2. Universidad Autonoma Metropolitana
  3. Columbia University
  4. COLUMBIA UNIVERSITY
  5. BATTELLE (PACIFIC NW LAB)

The structures of the dimers of formamide and N-methylacetamide have been calculated at the ab initio electronic structure theory level, 2nd order Miller-Plesset perturbation theory (MP2) with augmented correlation consistent basis sets. Five unique structures were optimized for the formamide dimers at the MP2/aug-cc-pVDZ and MP2/aug-cc-pVTZ levels. At the optimized geometries obtained with the aug-cc-pVTZ basis set, MP2 energies were evaluated with the aug-cc-pVQZ basis set allowing an extrapolation of the energies to the complete basis set limit. Four structures were found for the N-methylacetamide dimer at the MP2/aug-cc-pVDZ level and single point energies were calculated at the MP2/aug-cc-pVTZ level. In both systems, the basis set superposition error (BSSE) was estimated with the counterpoise method. The strength of the N-HiiiO=C bond has a mean value of 7.1 kcal/mol in the formamide dimers and a mean value of 8.6 kcal/mol in the N-methylacetamide dimers. The difference in hydrogen bond strengths is attributed to differences in basicity at the carbonyl oxygen receptor site. In several dimers C-HiiiO=C hydrogen bonds play an important role in stabilizing these intermolecular complexes increasing the interaction energy by 1.1 to 2.6 kcal/mol per interaction.

Research Organization:
Pacific Northwest National Lab., Richland, WA (US), Environmental Molecular Sciences Laboratory (US)
Sponsoring Organization:
US Department of Energy (US)
DOE Contract Number:
AC06-76RL01830
OSTI ID:
15004989
Report Number(s):
PNNL-SA-33725; 1796; KP1301030; TRN: US200321%%283
Journal Information:
Journal of Physical Chemistry A, Vol. 105, Issue 20; Other Information: PBD: 24 May 2001
Country of Publication:
United States
Language:
English