Cycloaddition of benzyne to armchair single-walled carbon nanotubes: [2 + 2] or [4 + 2]?
The reaction mechanism and regioselectivity of cycloaddition reactions of benzyne to armchair single-walled carbon nanotubes were investigated with quantum chemical methods. The [2 + 2] cycloaddition reaction follows the diradical mechanism, whereas the [4 + 2] cycloaddition reaction adopts the concerted mechanism. More importantly, the [2 + 2] product is always more stable thermodynamically than the [4 + 2] ones, regardless of the diameter, while the [4 + 2] cycloaddition becomes kinetically more favored as the diameter goes up.
Institute for Chemical Physics and Department of Chemistry, State Key Laboratory of Electrical Insulation and Power Equipment, Xi'an Jiaotong University , Xi'an 710049, China, and Fukui Institute for Fundamental Chemistry, Kyoto University , Kyoto 606-8103, Japan.
Tao
T
Yang
Xiang
X
Zhao
Shigeru
S
Nagase