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1 H NMR Spectroscopic Studies of the Conformational Isomers of Pyrrolidinofullerenes
Author(s) -
Lukoyanova Olena,
Kitaygorodskiy Alex,
Cardona Claudia M.,
Echegoyen Luis
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700591
Subject(s) - pyrrolidine , chemistry , moiety , adduct , protonation , nitrogen , solvent , stereochemistry , malonate , organic chemistry , ion
Abstract Mixed bis‐adduct derivatives of C 60 containing a pyrrolidine and a malonate methano group were synthesized. Three regioisomers, the e′ , the trans ‐2, and the trans ‐3, were isolated and characterized. In‐depth NMR studies of these methano‐pyrrolidinofullerenes showed that the nitrogen inversion on the pyrrolidine moiety is not a fast event in the 1 H NMR time scale as previously regarded. Solvent effects, variable temperature experiments, and protonation of the pyrrolidine nitrogen are addressed.