Related Experiment Video
Updated: Aug 9, 2026

Analyzing Protein Dynamics Using Hydrogen Exchange Mass Spectrometry
Published on: November 29, 2013
A computational study of the role of hydrogen bonds in SN1 and E1 reactions
Shinichi Yamabe1, Noriko Tsuchida
1Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan. yamabes@nara-edu.ac.jp
Abstract:
The reaction between tertiary butyl chloride and water clusters was examined by applying density functional theory calculations. The carbonium ion t-Bu(+) that is normally sandwiched between the water clusters was found to be absent, such that a Cbond;O covalent bond was formed in the intermediate (Int1) after heterolysis. An (H(2)O)(4) cluster is able to bridge the front and rear of the central carbon and promotes heterolysis. A correlation between bond interchanges at the central carbon and proton relays is presented. Stereochemical scrambling in the solvolysis products is discussed in terms of this correlation. In addition, an E1 pathway for the elimination product, iso-butene, is found from Int1.
More Related Videos
10:52Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics
Published on: April 12, 2019
05:57Synthesizing Amino Acids Modified with Reactive Carbonyls in Silico to Assess Structural Effects Using Molecular Dynamics Simulations
Published on: April 26, 2024
Related Concept Videos
SN2 Reaction: Mechanism
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
SN2 Reaction: Transition State
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
SN1 Reaction: Mechanism
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a polar...
Predicting Products: SN1 vs. SN2
With increased substitution on the alkyl halide,...
E2 Reaction: Kinetics and Mechanism
E1 Reaction: Kinetics and Mechanism