Intramolecular hydrogen bonding (proton transfer) of 1-phenyl-1,3-butanedione.

Hideyo Matsuzawa, Takashi Nakagaki, Makio Iwahashi

Index: J. Oleo Sci. 56(12) , 653-8, (2007)

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Abstract

Through the (1)H and (13)C NMR measurements for the symmetrical beta-diketones such as 2,4-pentanedione and 1,3-diphenyl-1,3-propanedione and unsymmetrical one such as 1-phenyl-1,3-butanedione at various concentrations and temperatures, we confirmed that 1-phenyl-1,3-butanedione in CDCl(3) exists as monomers in its relatively low concentration. In addition, the 1-phenyl-1,3-butanedione in CDCl(3) exists not as a keto-form but as two kinds of cis-enol forms. The proton transfer between the two kinds of cis-enols for 1-phenyl-1,3-butanedione was discussed thermodynamically; it is concluded that the OH proton of enol of 1-phenyl-1,3-butanedione is considerably located near the oxygen atom attached to the carbon atom linking to a phenyl group.