Research Article Open Access

Theoretical Study of the Proton Transfer in Enaminones

Rita Sabah Elias1
  • 1 Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah, Iraq

Abstract

Problem statement: Hydrogen bonding has a vital rule to unrevealed the nature of many different interactions both in gas phase and condensed media thus it is one of the most important concepts in chemistry. Enaminoes with their ability to form intrahydrogen bonded cheated rings represent one of the suitable compounds to study such concept. Approach: The three possible tautomers of eneminones were fully optimized at several theoretical levels including B3LYP with the 6-31+G(d,p), 6-311++G(d,p) and aug-cc-pVDZ basis sets as well as MP2/6-311++G(d,p) level of theory. Then a search for the possible transition state between the two most stable tautomers; the ketamine and the enolimine was done at the B3LYP/6-311++G(d,p) level of theory. Results: The ketamine is the most stable while the diketo is the less stable within the tautomeric mixture and the proton transfer occurs through a transition state that is energetically resemble the enolimine tautomer. Conclusion: The interconversion of the tautomers is preferable in the enolimine → ketamine direction.

American Journal of Applied Sciences
Volume 9 No. 1, 2012, 103-106

DOI: https://doi.org/10.3844/ajassp.2012.103.106

Submitted On: 3 September 2011 Published On: 23 November 2011

How to Cite: Elias, R. S. (2012). Theoretical Study of the Proton Transfer in Enaminones. American Journal of Applied Sciences, 9(1), 103-106. https://doi.org/10.3844/ajassp.2012.103.106

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Keywords

  • Proton transfer
  • intrahydrogen bonding
  • post hartree-fock
  • system enough
  • imaginary frequency
  • geometry optimized structures
  • tautomeric mixture
  • Transition State (TS)