%0 Journal Article
%A Zheng, Haiyan
%A Li, Kuo
%A Cody, George D.
%A Tulk, Christopher A.
%A Dong, Xiao
%A Gao, Guoying
%A Molaison, Jamie J.
%A Liu, Zhenxian
%A Feygenson, Mikhail
%A Yang, Wenge
%A Ivanov, Ilia N.
%A Basile, Leonardo
%A Idrobo, Juan-Carlos
%A Guthrie, Malcolm
%A Mao, Ho-kwang
%T Polymerization of Acetonitrile via a Hydrogen Transfer Reaction from CH 3 to CN under Extreme Conditions
%J Angewandte Chemie / International edition
%V 55
%N 39
%@ 1433-7851
%C Weinheim
%I Wiley-VCH
%M FZJ-2016-05538
%P 12040 - 12044
%D 2016
%X Acetonitrile (CH$_{3}$CN) is the simplest and one of the most stable nitriles. Reactions usually occur on the C≡N triple bond, while the C−H bond is very inert and can only be activated by a very strong base or a metal catalyst. It is demonstrated that C−H bonds can be activated by the cyano group under high pressure, but at room temperature. The hydrogen atom transfers from the CH3 to CN along the CH⋅⋅⋅N hydrogen bond, which produces an amino group and initiates polymerization to form a dimer, 1D chain, and 2D nanoribbon with mixed sp2 and sp3 bonded carbon. Finally, it transforms into a graphitic polymer by eliminating ammonia. This study shows that applying pressure can induce a distinctive reaction which is guided by the structure of the molecular crystal. It highlights the fact that very inert C−H can be activated by high pressure, even at room temperature and without a catalyst.
%F PUB:(DE-HGF)16
%9 Journal Article
%U <Go to ISI:>//WOS:000384713100062
%$ pmid:27561179
%R 10.1002/anie.201606198
%U https://juser.fz-juelich.de/record/819971