Abstract
A series of Schiff bases 7-11 derived from dibenzoylmethane have been prepared. The UV, IR, 1H NMR and mass spectra revealed theses compounds were existed mainly as the keto-enamine tautomer in the solution. The absorption bands which appeared in the range λmax = 376-406 nm were assigned to the electronic transitions which arised from the central hydrogen bonded chelated unsaturated ring system in this tautomer. The appearance of the broad singlet near d = 13 ppm due to the N-H proton and a singlet near d = 6 ppm due to the –C=C-H proton inaddition to benzoyl fragment ion signal m/z =105 in the mass spectra supported the above suggested products.
Highlights
The imines formation is a important chemical reaction in some biological processes [1, 2]
The utility of Schiff bases that derived from β-diketones as models in the investigation of the keto-enol tautomerism, their application as metal chelate catalysts and their analytical importance [13, 14] in addition to the fact that their metal chelates have conjugated systems similar to those of the synthetic chelated oxygen carriers [15, 16] have drown an increasing interest to them
These compounds could be exist as a tautomeric mixture of the enol-imine, the keto-imine and the keto-enamine tautomers: H
Summary
The imines formation is a important chemical reaction in some biological processes [1, 2]. The utility of Schiff bases that derived from β-diketones as models in the investigation of the keto-enol tautomerism, their application as metal chelate catalysts and their analytical importance [13, 14] in addition to the fact that their metal chelates have conjugated systems similar to those of the synthetic chelated oxygen carriers [15, 16] have drown an increasing interest to them. These compounds could be exist as a tautomeric mixture of the enol-imine, the keto-imine and the keto-enamine tautomers: H. This work is devoted to investigate the structures of some Schiff bases derived from dibenzoylmethane on the basis of their UV, IR, NMR, and mass spectra
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