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).
Internal motions in a fulleropyrrolidine tertiary amide with axial chirality / Borsato, Giuseppe; Della Negra, Federico; Gasparrini, Francesco; Misiti, Domenico; Lucchini, Vittorio; Possamai, Giorgia; Villani, Claudio; Zambon, Alfonso. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 69:17(2004), pp. 5785-5788. [10.1021/jo049485q]
Internal motions in a fulleropyrrolidine tertiary amide with axial chirality
ZAMBON, Alfonso
2004
Abstract
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).
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