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Synthesis, Structure, and Theoretical Study of Trifluoromethyl Derivatives of C 84 (22) Fullerene
Author(s) -
Chang Kaichin,
Fritz Maria A.,
Tamm Nadezhda B.,
Goryunkov Alexey A.,
Sidorov Lev N.,
Chen Chuanbao,
Yang Shangfeng,
Kemnitz Erhard,
Troyanov Sergey I.
Publication year - 2013
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.201202568
Subject(s) - fullerene , trifluoromethylation , chemistry , trifluoromethyl , crystal structure , crystallography , stereochemistry , computational chemistry , organic chemistry , alkyl
Trifluoromethylation of higher fullerene mixtures with CF 3 I was performed in ampoules at 400 to 420 and 550 to 560 °C. HPLC separation followed by crystal growth and X‐ray diffraction studies allowed the structure elucidation of nine CF 3 derivatives of D 2 ‐C 84 (isomer 22). Molecular structures of two isomers of C 84 (22)(CF 3 ) 12 , two isomers of C 84 (22)(CF 3 ) 14 , four isomers of C 84 (22)(CF 3 ) 16 , and one isomer of C 84 (22)(CF 3 ) 20 were discussed in terms of their addition patterns and relative formation energies. DFT calculations were also used to predict the most stable molecular structures of lower CF 3 derivatives, C 84 (22)(CF 3 ) 2–10 . It was found that the addition of CF 3 groups to C 84 (22) is governed by two rules: additions can only occur at para positions of C 6 (CF 3 ) 2 hexagons and no additions can occur at triple‐hexagon‐junction positions on the fullerene cage.