Related Experiment Video
Updated: Oct 6, 2025
Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Nucleophilicity and Electrophilicity in the Gas Phase: Silane Hydricity
Allison E Krajewski1, Jeehiun K Lee1
1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08901, United States.
Abstract:
Hydricity is of great import as hydride transfer reactions are prominent in many processes, including organic synthesis, photoelectrocatalysis, and hydrogen activation. Herein, the kinetic hydricity of a series of silanes is examined in the gas phase. Most of these reactions have not heretofore been studied in vacuo and provide valuable data that can be compared to condensed-phase hydricity, to reveal the effects of solvent. Both experiments and computations are used to gain insight into mechanism and reactivity. In a broader sense, these studies also represent a first step toward systematically understanding nucleophilicity and electrophilicity in the absence of a solvent.
Related Concept Videos
02:28Electrophiles
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
02:30Nucleophiles
02:34Nucleophilic Substitution Reactions
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
02:42Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
02:54Lewis Structures of Molecular Compounds and Polyatomic Ions