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Issue 6, 2017
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Double C–H bond activation of acetylene by atomic boron in forming aromatic cyclic-HBC2BH in solid neon

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Abstract

The organo-boron species formed from the reactions of boron atoms with acetylene in solid neon are investigated using matrix isolation infrared spectroscopy with isotopic substitutions as well as quantum chemical calculations. Besides the previously reported single C–H bond activation species, a cyclic-HBC2BH diboron species is formed via double C–H bond activation of acetylene. It is characterized to have a closed-shell singlet ground state with planar D2h symmetry. Bonding analysis indicates that it is a doubly aromatic species involving two delocalized σ electrons and two delocalized π electrons. This finding reveals the very first example of double C–H bond activation of acetylene in forming new organo-boron compounds.

Graphical abstract: Double C–H bond activation of acetylene by atomic boron in forming aromatic cyclic-HBC2BH in solid neon

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Supplementary files

Article information


Submitted
29 Mar 2017
Accepted
12 Apr 2017
First published
19 Apr 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 4443-4449
Article type
Edge Article

Double C–H bond activation of acetylene by atomic boron in forming aromatic cyclic-HBC2BH in solid neon

J. Jian, W. Li, X. Wu and M. Zhou, Chem. Sci., 2017, 8, 4443
DOI: 10.1039/C7SC01399J

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