Related Experiment Video
Updated: Feb 7, 2026

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin
Published on: July 23, 2016
SN2 Reactions in Hydrocarbon Solvents Using Ammonium-Terminated Polyisobutylene Oligomers as Phase-Solubilizing
Peerada Samunual1, David E Bergbreiter1
1Department of Chemistry , Texas A&M University , P.O. Box 30012, College Station , Texas 77842-3012 , United States.
Abstract:
Although SN2 reactions have been thoroughly studied in polar aprotic and protic solvents, not many studies have been done to study the rate of SN2 reaction in nonpolar solvents like alkanes due to the insolubility of anionic nucleophiles in these solvents. In this study, we investigated the use of N,N-diethyl- N-methylammonium-terminated polyisobutylene oligomers as phase-solubilizing agents for nucleophilic anions that could react with hydrocarbon-soluble substrates in alkanes. The results of these kinetic studies showed alkanes were comparable to MeCN as solvents in many reactions. Based on these studies, we developed a solid/liquid catalytic process using insoluble alkali metal carboxylate salts and a recyclable soluble polyisobutylene-bound catalyst that can be used to carry out SN2 reactions both in heptane and in hydrocarbon oligomeric solvents known as poly(α-olefins) (PAOs).
More Related Videos
Related Concept Videos
Phase I Reactions: Hydrolytic Reactions
An important hydrolytic reaction is ester hydrolysis. Ester bonds, often found in prodrugs, are broken down, increasing the solubility of drugs like aspirin and lidocaine for more straightforward elimination. Amide hydrolysis is another critical reaction, targeting amide bonds prevalent...
Phase II Reactions: Acetylation Reactions
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...
Phase I Reactions: Reductive Reactions
Phase II Reactions: Methylation Reactions
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
Phase II Reactions: Miscellaneous Conjugation Reactions
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...
Phase II Reactions: Glucuronidation

