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1 Polish Journal of Chemistry

1 1998

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(13)C kinetic isotope effects in the decarboxylation of phenylpropiolic acid (PPA) assisted with formic acid and (13)C KIE in the decarbonylation of formic acid in the presence of PPA

Zieliński M., Zielińska A., Paul H., Papiernik-Zielińska H.

Polish Journal of Chemistry

1998

Vol. 72, nr 12

2551-2555

Carbon-13 kinetic isotope effects, (13)C-KIE, in the decarboxylation of phenylpropiolic acid (carboxyl C-13) in formic acid medium and (13)C KIE in the decarbonylation of liquid formic acid assisted with PPA and acetophenone have been studied in the 70-100 degree C temperature interval. The kinetic and isotope results have been discussed and interpreted as indicating that the formation of C alpha-H bond, preceded by the protonation of acetylenic bond of PPA, is the rate determining step followed by carbon dioxide splitting. The (13)CO-KIE in the carbon monoxide generation assisted with PPA is much larger than the (13)CO-KIE observed in the generation of CO in the presence of phenylacetylene. Thus the decaeboxylation of PPA and decarbonylation of formic acid are interrelated processes proceeding in the reaction cage.