Related Experiment Video
Updated: Aug 4, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Understanding the Reactivity of Diazaborinines towards the Activation of σ-Bonds
Susana Portela1, Israel Fernández1
1Departamento de Química Orgánica y Centro de Innovación en Química Avanzada (ORFEO-CINQA) Facultad de Ciencias Químicas, Universidad Complutense de Madrid Ciudad Universitaria, 28040-, Madrid, Spain.
Abstract:
The poorly understood factors governing the small molecule activation reactions mediated by diazaborinines have been computationally explored in detail using quantum chemical tools. To this end, the activation of E-H σ-bonds (E = H, C, Si, N, P, O, S) has been investigated. These reactions, which proceed in a concerted manner, are exergonic and, in general, associated with relatively low activation barriers. In addition, the barrier becomes lower for the E-H bonds involving the heavier element in the same group (ΔG≠ : C>Si; N>P; O>S). This reactivity trend together with the mode of action of the diazaborinine system are quantitatively analyzed by means of the activation strain model of reactivity in combination with the energy decomposition analysis method.
More Related Videos
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Diazonium Group Substitution: –OH and –H
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

