American Chemical Society
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Internal Motions in a Fulleropyrrolidine Tertiary Amide with Axial Chirality

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journal contribution
posted on 2004-08-20, 00:00 authored by Giuseppe Borsato, Federico Della Negra, Francesco Gasparrini, Domenico Misiti, Vittorio Lucchini, Giorgia Possamai, Claudio Villani, Alfonso Zambon
The kinetic parameters for topomerization around the N−CO bond and enantiomerization around the C−CO bond in N-1-naphthoyl fulleropyrrolidine 1 and N-1-naphthoyl pyrrolidine 2 have been determined by dynamic NMR (line shape simulation and selective inversion transfer). The ΔS values are negligible. The ΔH# value for topomerization of 1 is smaller with respect to that of 2 by 4.3 kcal mol-1 (explained by the electron-withdrawing effect of fullerene) and the value for enantiomerization is greater by 1.4 kcal mol-1 (explained by the greater rigidity of the fulleropyrrolidine ring, as confirmed by ab initio analyses).