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Engineering the Frontier Orbitals of a Diazadiborinine for Facile Activation of H 2 , NH 3 , and an Isonitrile
Author(s) -
Su Yuanting,
Li Yongxin,
Ganguly Rakesh,
Kinjo Rei
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201803938
Subject(s) - reactivity (psychology) , cycloaddition , atomic orbital , chemistry , homo/lumo , molecule , molecular orbital , ammonia , computational chemistry , electron , photochemistry , organic chemistry , catalysis , physics , medicine , alternative medicine , pathology , quantum mechanics
An annulated 1,3,2,5‐diazadiborinine with 14 π electrons has been synthesized and fully characterized. Experimental and computational studies revealed that this compound features a rather small HOMO–LUMO gap, which leads to enhanced reactivity towards small molecules. Thus, the 1,3,2,5‐diazadiborinine readily cleaves the H−H bond of dihydrogen and an N−H bond of ammonia under mild conditions. Moreover, it reacts with 2,6‐dimethylphenylisonitrile in a [4+1] cycloaddition at room temperature.