Functionalization of fullerene via the Bingel reaction with α-chlorocarbanions: an ONIOM approach

Nguyen Minh Thong; Thi Chinh Ngo; Duy Quang Dao; Tran Duong; Quoc Tri Tran; Pham Cam Nam

doi:10.1007/s00894-016-2981-5

Functionalization of fullerene via the Bingel reaction with α-chlorocarbanions: an ONIOM approach

J Mol Model. 2016 May;22(5):113. doi: 10.1007/s00894-016-2981-5. Epub 2016 Apr 25.

Authors

Nguyen Minh Thong^{1

2}, Thi Chinh Ngo³, Duy Quang Dao³, Tran Duong⁴, Quoc Tri Tran⁵, Pham Cam Nam⁶

Affiliations

¹ The University of Danang, Campus in Kon Tum, 704, Phan Dinh Phung, Kon Tum, Vietnam.
² Department of Chemistry, Hue University of Sciences, 77 Nguyen, Hue, Hue, Vietnam.
³ Institute of Research and Development, Duy Tan University, K7/25 Quang Trung, Da Nang, Vietnam.
⁴ Department of Chemistry, Hue's University College of Education, 34 Le Loi, Hue, Vietnam.
⁵ Dong Thap University, 873 Pham Huu Lau, Cao Lanh, Vietnam.
⁶ Department of Chemistry, University of Science and Technology - The University of Danang, 54 Nguyen Luong Bang, Lien Chieu, Da Nang, Vietnam. [email protected].

PMID: 27114364
DOI: 10.1007/s00894-016-2981-5

Abstract

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.

Keywords: Bingel reaction; Fukui function; Fullerene; Mulliken charge; Natural bond orbital; ONIOM; α-chlorocarbanions.

Publication types

Research Support, Non-U.S. Gov't