NMR study of kinetic HH/HD/DH/DD isotope effects on the tautomerism of acetylporphyrin: evidence for a stepwise double proton transfer

M Schlabach, HH Limbach, E Bunnenberg…

Index: Schlabach, Martin; Limbach, Hans-Heinrich; Bunnenberg, Edward; Shu, Arthur Y.L.; Tolf, Bo-Ragnar; Djerassi, Carl Journal of the American Chemical Society, 1993 , vol. 115, # 11 p. 4554 - 4565

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Citation Number: 57

Abstract

Abstract: The kinetic HH/HD/DH/DD isotope effects of an intramolecular reversible nondegenerate double proton transfer reaction are described. The molecule studied is 8- acetyl-3, 13, 17-tris [2-(methoxycarbonyl) ethyl]-2, 7, 12, 18-tetramethyl-(21H, 23H)- porphyrin (acetylporphyrin, ACP) dissolved in CD2C12. As a thermodynamic and kinetic method we used dynamic IH and 13C NMR spectroscopy of suitably 2H, 15N, and I3C ...