通过狄尔斯-阿尔德反应实现碳纳米管侧壁的有机功能化：一项理论预测。

Organic functionalization of the sidewalls of carbon nanotubes by diels-alder reactions: a theoretical prediction.

作者信息

Lu Xin, Tian Feng, Wang Nanqin, Zhang Qianer

机构信息

State Key Laboratory for Physical Chemistry of Solid Surfaces, Institute of Physical Chemistry, Department of Chemistry, Xiamen University, Xiamen 361005, China.

出版信息

Org Lett. 2002 Nov 28;4(24):4313-5. doi: 10.1021/ol026956r.

DOI:10.1021/ol026956r

PMID:12443086

Abstract

[structure: see text] The viability of the Diels-Alder (DA) cycloaddition of conjugated dienes onto the sidewalls of single-wall carbon nanotubes is assessed by means of a two-layered ONIOM(B3LYP/6-31G:AM1) approach. Whereas the DA reaction of 1,3-butadiene on the sidewall of an armchair (5,5) nanotube is found to be unfavorable, the cycloaddition of quinodimethane is predicted to be viable due to the aromaticity stabilization at the corresponding transition states and products.

摘要

[结构：见正文] 通过两层ONIOM(B3LYP/6 - 31G:AM1)方法评估共轭二烯与单壁碳纳米管侧壁发生狄尔斯-阿尔德（DA）环加成反应的可行性。虽然发现1,3 - 丁二烯在扶手椅型(5,5)纳米管侧壁上的DA反应不利，但由于相应过渡态和产物处的芳香性稳定作用，预计醌二甲烷的环加成反应是可行的。