Solvent effect in keto–enol tautomerism for a polymerizable β-ketonitrile monomer. Spectroscopy and theoretical study

• A beta-ketonitrile studied by NMR spectroscopy and DFT methods.
• Experimental and calculated NMR chemical shifts showed good correlation.
• Enol content increases with solvent polarity.

The beta-ketonitrile 2-methyl-5-phenyl-3-oxo-4-pentenenitrile, a polymerizable monomer, exists in two important tautomeric forms, keto and enol isomers. This compound has been studied as monomer in polymerization reactions and the resulting polymers have been applied in fields of nanotechnology. Currently, these are being studied in nanomedicine. To understand the tautomeric equilibrium, we have studied this compound in solution by NMR spectrometry. Correlation with DFT calculations has been carried out in order to understand the system behavior. The results found in this work, both by experiments and calculations, show that the enol content increases with solvent polarity.

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