Functionalization of fullerene via the Bingel reaction with α-chlorocarbanions: an ONIOM approach.
Two-layer ONIOM method at the ONIOM(B3LYP/6-31G(d):PM6) level of theory was applied to study the cycloaddition reaction of α-chlorocarbanions (CR2Cl(─), where R is H, Cl, CH3 CN, and NO2) and fullerene. The results show that the reaction pathways depend on the electron withdrawing functional groups or the electron donating functional groups contained in the α-chlorocarbanions. The energy profile analysis reveals that functionalization of fullerene by CCl3 (─), C(CH3)2Cl(─), and CH2Cl(─) is more favorable than by C(CN)2Cl(─) and C(NO2)2Cl(─) in terms of the thermodynamic point of view.
The University of Danang, Campus in Kon Tum, 704, Phan Dinh Phung, Kon Tum, Vietnam.|Department of Chemistry, Hue University of Sciences, 77 Nguyen, Hue, Hue, Vietnam.
Nguyen Minh
NM
Thong
Institute of Research and Development, Duy Tan University, K7/25 Quang Trung, Da Nang, Vietnam.
Thi Chinh
TC
Ngo
Institute of Research and Development, Duy Tan University, K7/25 Quang Trung, Da Nang, Vietnam.
Duy Quang
DQ
Dao
Department of Chemistry, Hue's University College of Education, 34 Le Loi, Hue, Vietnam.
Tran
T
Duong
Dong Thap University, 873 Pham Huu Lau, Cao Lanh, Vietnam.
Quoc Tri
QT
Tran
Department of Chemistry, University of Science and Technology - The University of Danang, 54 Nguyen Luong Bang, Lien Chieu, Da Nang, Vietnam. camnamp@yahoo.com.
Pham Cam
PC
Nam
Bingel reaction; Fukui function; Fullerene; Mulliken charge; Natural bond orbital; ONIOM; α-chlorocarbanions