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Issue 31, 2010
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A chemical dynamics, kinetics, and theoretical study on the reaction of the cyano radical (CN; X2Σ+) with phenylacetylene (C6H5CCH; X1A1)

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Abstract

The chemical reaction dynamics to form o-, m-, and p-cyanophenylacetylene via the neutral–neutral reaction of ground state cyano radicals with phenylacetylene and D1-phenylacetylene were investigated in crossed beam experiments; these studies were combined with kinetics measurements of the rate coefficients at temperatures of 123, 200, and 298 K and supplemented by electronic structure calculations. The data suggest that the reaction is initiated by a barrier-less addition of the electrophilic cyano radical to the o-, m-, or p-position of the aromatic ring. The eventually fragmented via atomic hydrogen elimination to form o-, m-, and p-cyanophenylacetylene via tight exit transition states with the hydrogen atom being ejected almost perpendicularly to the molecular plane of the rotating complex. The overall reaction to form o-, m-, and p-cyanophenylacetylene was found to be exoergic by 89 ± 18 kJ mol−1 in nice agreement with the calculations. The o-cyanophenylacetylene isomer is of particular relevance as a potential building block to the formation of nitrogen-substituted didehydronaphthalene molecules in analogy to didehydronaphthalene in Titan's aerosol layers—a pathway hitherto neglected by the planetary science modeling community.

Graphical abstract: A chemical dynamics, kinetics, and theoretical study on the reaction of the cyano radical (CN; X2Σ+) with phenylacetylene (C6H5CCH; X1A1)

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Article information


Submitted
30 Nov 2009
Accepted
26 Feb 2010
First published
06 Apr 2010

Phys. Chem. Chem. Phys., 2010,12, 8737-8749
Article type
Paper

A chemical dynamics, kinetics, and theoretical study on the reaction of the cyano radical (CN; X2Σ+) with phenylacetylene (C6H5CCH; X1A1)

C. J. Bennett, S. B. Morales, S. D. Le Picard, A. Canosa, I. R. Sims, Y. H. Shih, A. H. H. Chang, X. Gu, F. Zhang and R. I. Kaiser, Phys. Chem. Chem. Phys., 2010, 12, 8737
DOI: 10.1039/B925072G

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