PMID: 11322551Apr 27, 2001Paper

A study of gas-phase reactions of radical cations of mono- and dihaloethenes with alcohols by FT-ICR spectrometry and molecular orbital calculations: substitution versus oxidation

Chemistry : a European Journal
A Nixdorf, H F Grützmacher

Abstract

The ion-molecule reactions of the radical cations of vinyl chloride (1), vinyl bromide (2), 1,2-dichloroethene (3), 1,2-dibromoethene (4), 1,1-dichloroethene (5), and 1,1-dibromoethene (6) with methanol (MeOH) and ethanol (EtOH) have been studied by FT-ICR spectrometry. In the case of EtOH as reactant the oxidation of the alcohol to protonated acetaldehyde by a formal hydride transfer to the haloethene radical cation is the main process if not only reaction observed with the exception of the 1,2-dibromoethene radical cation which exhibits slow substitution. In secondary reactions the protonated acetaldehyde transfers the proton to EtOH which subsequently undergoes a well known condensation reaction of EtOH to form protonated diethyl ether. With MeOH as reactant, the 1,2-dihaloethene radical cations of 3.+ and 4.+ exhibit no reaction, while the other haloethene radical cations undergo the analogous reaction sequence of oxidation yielding protonated formaldehyde. Generally, bromo derivatives of haloethene radical cations react predominantly by substitution and chloro derivatives by oxidation. This selectivity can be understood by the thermochemistry of the competing processes which favors substitution of Br while the effect of th...Continue Reading

References

Mar 1, 1999·Angewandte Chemie·Sason Shaik, Avital Shurki

❮ Previous
Next ❯

Citations

May 14, 2003·Journal of Colloid and Interface Science·Jimmy C YuJun Lin
Oct 31, 2002·Ultrasonics Sonochemistry·Yanqin WangArahon Gedanken
Oct 31, 2017·Mass Spectrometry Reviews·Dirk NoltingAlexander Makarov
Aug 30, 2008·The Journal of Physical Chemistry. a·Victor A MikhailovChris A Mayhew
Mar 11, 2006·The Journal of Organic Chemistry·Micha SlegtGerrit Lodder
Apr 28, 2006·The Journal of Physical Chemistry. a·Victor A MikhailovChris A Mayhew

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.