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Solid‐State NMR Study of the Tautomerism of Acetylacetone Included in a Host Matrix
Author(s) -
Claramunt Rosa M.,
López Concepción,
Lott Susanne,
Santa María M. Dolores,
Alkorta Ibon,
Elguero José
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590148
Subject(s) - tautomer , chemistry , acetylacetone , enol , pentane , nuclear magnetic resonance spectroscopy , keto–enol tautomerism , spectroscopy , matrix isolation , computational chemistry , photochemistry , infrared spectroscopy , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
The tautomerism of the enol form of acetylacetone (=pentane‐2,4‐dione; 1 ) inside a host cavity has been studied by means of solid‐state 13 C‐NMR spectroscopy (SSNMR) using the variable‐temperature CPMAS technique. It appears that the enol form, 4‐hydroxypent‐3‐en‐2‐one ( 1a ), exists in an equilibrium with an identical tautomer ( 1c ) trough OH ⋅⋅⋅O proton transfer. The experimental results (energy barrier and chemical shifts) were rationalized by means of MP2 and GIAO calculations.