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Endohedral Regulator for Metallofullerene Chemical Property: Diels–Alder Reaction Studies of Sc x Y 3‐ x N@C 80 ‐ I h ( x =0‐3)
Author(s) -
Zhang Zhuxia,
Xue Wenhua,
Jia Wei,
Zhang Caili,
Zhang Jie,
Zhang Yong,
Wang Lan,
Guo Zhen,
Cui Peng
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201703087
Subject(s) - adduct , reactivity (psychology) , metallofullerene , chemistry , regioselectivity , decomposition , stereochemistry , crystallography , metal , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology , catalysis
Chemical functionalization is an important method modulating the chemical properties of endohedral metallofullerene. In this study, Diels–Alder reaction of Sc x Y 3‐ x N@C 80 ‐ I h ( x =0‐3) with o ‐quinodimethane was investigated both experimentally and theoretically. There is only one regioselective mono‐[5, 6]‐adduct isolated for Sc 3 N@C 80 , Sc 2 YN@C 80 and ScY 2 N@C 80 , respectively and one mono‐[5, 6] and one mono‐[6, 6]‐adduct obtained for Y 3 N@C 80 . The calculated results showed that the entrapped Sc x Y 3‐ x N clusters in the cage have the same orientation with two metal atoms toward adduct sites in the thermodynamically stable DA‐[5, 6]‐adducts. They all have higher chemical reactivity. The similar stabilizing and destabilizing effects on reactivity were found by the Activation Strain Model of reactivity and Energy Decomposition Analysis method.