Ambiphilic boron in 1,4,2,5-diazadiborinine

Baolin Wang, Yongxin Li, Rakesh Ganguly, Hajime Hirao () and Rei Kinjo ()
Additional contact information
Baolin Wang: School of Physical and Mathematical Sciences, Nanyang Technological University
Yongxin Li: NTU-SPMS-CBC Crystallography Facility, Nanyang Technological University
Rakesh Ganguly: NTU-SPMS-CBC Crystallography Facility, Nanyang Technological University
Hajime Hirao: School of Physical and Mathematical Sciences, Nanyang Technological University
Rei Kinjo: School of Physical and Mathematical Sciences, Nanyang Technological University

Nature Communications, 2016, vol. 7, issue 1, 1-10

Abstract: Abstract Boranes have long been known as the archetypal Lewis acids owing to an empty p-orbital on the boron centre. Meanwhile, Lewis basic tricoordinate boranes have been developed in recent years. Here we report the synthesis of an annulated 1,4,2,5-diazadiborinine derivative featuring boron atoms that exhibit both Lewis acidic and basic properties. Experimental and computational studies confirmed that two boron atoms in this molecule are spectroscopically equivalent. Nevertheless, this molecule cleaves C–O, B–H, Si–H and P–H bonds heterolytically, and readily undergoes [4+2] cycloaddition reaction with non-activated unsaturated bonds such as C=O, C=C, C≡C and C≡N bonds. The result, thus, indicates that the indistinguishable boron atoms in 1,4,2,5-diazadiborinine act as both nucleophilic and electrophilic centres, demonstrating ambiphilic nature.

Date: 2016
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/ncomms11871 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms11871

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/ncomms11871

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().