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Diels–Alder Reactivity of Metallofullerene Sc 3 N@C 78 and Structure Elucidation on Its Products
Author(s) -
Zhang Zhuxia,
Zhang Yong,
Xue Wenhua,
Guo Zhen,
Cui Peng
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701427
Subject(s) - metallofullerene , cycloaddition , regioselectivity , diels–alder reaction , adduct , reactivity (psychology) , chemistry , fullerene , computational chemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The Diels–Alder reaction of Sc 3 N@C 78 with o ‐quinodimethane was studied through experimental and theoretical methods. Four isomers for Sc 3 N@C 78 monoadduct were discovered in experiment and the possible cycloaddition sites were analyzed by means of theoretical calculations. The results revealed that the major isomers can be assigned to the thermodynamically and kinetically favorable [6, 6] adduct, indicating that the cycloaddition reaction takes place in the bond between two hexagonal rings of C 78 cage. The high regioselectivity of Diels–Alder reaction on Sc 3 N@C 78 was also discussed by means of structure and reaction barrier analyses.