Original scientific paper

Proton and Lithium Cation Binding to Some β-Dicarbonyl Compounds. A Theoretical Study

Peeter Burk ; Institute of Chemistry, Tartu University, 2 Jakobi St., Tartu, 51014, Estonia
Kristo Taul ; Institute of Chemistry, Tartu University, 2 Jakobi St., Tartu, 51014, Estonia
Jaana Tammiku-Taul ; Institute of Chemistry, Tartu University, 2 Jakobi St., Tartu, 51014, Estonia

Abstract

DFT B3LYP/6-311+G** calculations were performed to study the proton and lithium cation binding to the acetylacetone, hexafluoroacetylacetone, diacetamide, and hexafluorodiacetamide. It was shown that the most stable Li+ adduct always corresponds to cyclic complex based on the trans, trans-keto
form of the base. The product of protonation was found to be similar trans, trans-keto form based cyclic structure in case of diacetamide and hexafluorodiacetamide, while for acetylacetone and hexafluoroacetylacetone the protonation simply involves the addition of proton to (free) carbonyl oxygen in already cyclic enol form of the base with possible rotation of O−H bond.

Keywords

keto-enol tautomerism; proton affinity; lithium cation afifinity; DFT calculations

Hrčak ID:

37980

URI

https://hrcak.srce.hr/37980

Publication date:

30.6.2009.

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