Hydrogen bonding in acetylacetaldehyde: Theoretical insights from the theory of atoms in molecules

A. Nowroozi, A. F. Jalbout, H. Roohi, E. Khalilinia, M. Sadeghi, A. De Leon*, H. Raissi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

All the possible conformations of tautomeric structures (keto and enol) of acetylacetaldehyde (AAD) were fully optimized at HF, B3LYP, and MP2 levels with 6-31G(d,p) and 6-311+ + (d,p) basis sets to determine the conformational equilibrium. Theoretical results show that two chelated enol forms have extra stability with respect to the other conformers, but identification of global minimum is very difficult. The high level ab initio calculations G2(MP2) and CBS-QB3) also support the HF conclusion. It seems that the chelated enol forms have equal stability, and the energy gap between them is probably lies in the computational error range. Finally, the analysis of hydrogen bond in these molecules by quantum theory of atoms in molecules (AIM) and natural bond orbital (NBO) methods fairly support the ab initio results.

Original languageEnglish
Pages (from-to)1505-1514
Number of pages10
JournalInternational Journal of Quantum Chemistry
Volume109
Issue number7
DOIs
StatePublished - 2009
Externally publishedYes

Keywords

  • AIM
  • Ab initio
  • Acetylacetaldehyde
  • Intramolecular hydrogen bond
  • NBO

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