Related Experiment Video
Updated: Jun 20, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
Oxidative addition reactions of element-hydrogen bonds with different polarities to a gallium(I) compound
Annekathrin Seifert1, Dominik Scheid, Gerald Linti
1Universität Heidelberg, Anorganisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Abstract:
The gallium(I) derivative [Ga({N(dipp)CMe}(2)CH)] (1; dipp = 2,6-diisopropylphenyl) undergoes facile oxidative addition reactions with various element-hydrogen bonds including N-H, P-H, O-H, Sn-H, and H-H bonds. This was demonstrated by its reaction with triphenyltin hydride, ethanol, water, diethylamine, diphenylphosphane, and dihydrogen. All products were characterized by means of single-crystal X-ray structure determination, NMR spectroscopy, IR spectroscopy, and mass spectrometry.
Related Concept Videos
Introduction to Electrophilic Addition Reactions of Alkenes
Addition and elimination reactions can be...
Electrophilic Addition to Alkynes: Hydrohalogenation
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Halogens
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Radical 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,...

