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Issue 12, 2013
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DFT investigation of C–H bond activation of malononitrile in the presence of amines

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Abstract

DFT investigations of the isomerization and deprotonation of malononitrile by the amines were performed at the B3LYP/6-31++G** level. Calculations indicate that isomerization of malononitrile is difficult to achieve without promoters because of high energy barriers. Basic N atoms in amines can abstract an H atom from malononitrile. Activation barriers for proton abstraction are highly correlated with the available or estimated pKa values of protonated amines. The reaction mechanism can be deduced from the slope of the Brönsted plot. This work suggests an efficient catalyst, N-1, based on computational results.

Graphical abstract: DFT investigation of C–H bond activation of malononitrile in the presence of amines

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Publication details

The article was received on 23 Jun 2013, accepted on 30 Sep 2013 and first published on 02 Oct 2013


Article type: Paper
DOI: 10.1039/C3NJ00678F
Citation: New J. Chem., 2013,37, 3920-3927
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    DFT investigation of C–H bond activation of malononitrile in the presence of amines

    Z. Su and C. Kyung Kim, New J. Chem., 2013, 37, 3920
    DOI: 10.1039/C3NJ00678F

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