Diels–Alder Reactivity of Metallofullerene Sc3N@C78 and Structure Elucidation on Its Products. Issue 28 (2nd October 2017)

• Record Type: Journal Article
• Authors: Zhang, Zhuxia; Zhang, Yong; Xue, Wenhua; Guo, Zhen; Cui, Peng
• Is Part Of: ChemistrySelect. Volume 2:Issue 28(2017)
• Page Start: 8880
• Page End: 8885
• Publication Date: 2017-10-02
• Subjects: cycloaddition sites -- Diels–Alder Reactivity -- Metallofullerene -- Sc3N@C78 -- theoretical calculations; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201701427
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: The Diels–Alder reaction of Sc3 N@C78 with o ‐quinodimethane was studied through experimental and theoretical methods. Four isomers for Sc3 N@C78 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 C78 cage. The high regioselectivity of Diels–Alder reaction on Sc3 N@C78 was also discussed by means of structure and reaction barrier analyses. Abstract : The external modification on metallofullerenes plays an important role in manipulating their structure and functions. In this manuscript, the Diels–Alder reaction of o ‐quinodimethane to D3h ‐Sc3 N@C78 was studied by both density functional theory calculations and experiments. Four isomers for Sc3 N@C78 monoadduct were discovered and the possible cycloaddition sites were analyzed by means of theoretical calculations. The major isomers can be assigned to the thermodynamically and kinetically favorable [6, 6] adduct.