Related Experiment Video
Updated: Mar 5, 2026
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Dehydrogenation of icosahedral carborane anions via gas-phase collisional activation
Omar M Hamdy1, Huong T Pham1, Scott G McArthur1
1Department of Chemistry, University of California, Riverside, CA, 92521, USA.
Rationale:
The icosahedral carborane anion HCB11 H11-1 is well known for its exceptional stability in solution and the solid state, but the gas-phase properties of this molecule have not previously been explored.
Methods:
Electrospray ionization ion trap mass spectrometry, collisional activation, and isotopic labelling were used to examine the formation and reaction pathways of covalent and noncovalent carborane clusters.
Results:
Covalent attachment of an amino group to the C-vertex of HCB11 H11-1 dramatically alters its stability in the gas phase. Interestingly, covalently bound carborane dimers are produced during electrospray ionization. Subsequent collisional activation of these dimers leads to facile hydrogen losses (7 H2 molecules). The loss of H2 does not follow a stochastic pattern, but occurs preferentially by loss of 3 H2 , followed by loss of 2 H2 and then another 2 H2 molecules.
Conclusions:
This study provides insight into new possible modes of B-H activation and functionalization in carborane cages. Copyright © 2016 John Wiley & Sons, Ltd.
More Related Videos
14:07Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
03:08Hydroboration-Oxidation of Alkenes
01:26Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
02:10Carbocations
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration