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Title: 1,3,2,5-Diazadiborinine featuring nucleophilic and electrophilic boron centres
Authors: Wu, Di
Kong, Lingbing
Li, Yongxin
Ganguly, Rakesh
Kinjo, Rei
Issue Date: 2015
Source: Wu, D., Kong, L., Li, Y., Ganguly, R., & Kinjo, R. (2015). 1,3,2,5-Diazadiborinine featuring nucleophilic and electrophilic boron centres. Nature Communications, 6, 7340-.
Series/Report no.: Nature communications
Abstract: The seminal discovery in 1865 by Kekulé that benzene nucleus exists with cyclic skeleton is considered to be the beginning of aromatic chemistry. Since then, a myriad of cyclic molecules displaying aromatic property have been synthesized. Meanwhile, borazine (B3N3H6), despite the isostructural and isoelectronic relationships with benzene, exhibits little aromaticity. Herein, we report the synthesis of a 1,3,2,5-diazadiborinine (B2C2N2R6) derivative, a hybrid inorganic/organic benzene, and we present experimental and computational evidence for its aromaticity. In marked contrast to the reactivity of benzene, borazine, and even azaborinines previously reported, 1,3,2,5-diazadiborinine readily forms the adducts with methyl trifluoromethanesulfonate and phenylacetylene without any catalysts. Moreover, 1,3,2,5-diazadiborine activates carbon dioxide giving rise to a bicycle[2,2,2] product, and the binding process was found to be reversible. These results, thus, demonstrate that 1,3,2,5-diazadiborinine features both nucleophilic and electrophilic boron centres, with a formal B(+I)/B(+III) mixed valence system, in the aromatic six-membered B2C2N2 ring.
ISSN: 2041-1723
DOI: 10.1038/ncomms8340
Schools: School of Physical and Mathematical Sciences 
Rights: © 2015 Macmillan Publishers Limited. This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit
Fulltext Permission: open
Fulltext Availability: With Fulltext
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