Influence of Lewis acid strength on hydride transfer to unsaturated substrates

Dalton Transactions : an International Journal of Inorganic Chemistry
Ian A KiefferZachariah M Heiden

Abstract

Hydride transfer promoted by the coordination of a substrate molecule to a Lewis acid is a critical step in many catalytic transformations. This computational study investigates the nature of the interaction between a polar substrate molecule and a Lewis acid by examining the influence of Lewis acid strength on the ability to reduce (transfer a hydride to) the coordinated substrate molecule. To investigate this interaction, the coordination of 10 probe substrates to seven Lewis acids was analyzed. Coordination of the probe substrate molecules to a Lewis acid resulted in a more favorable reduction of the substrate molecule by 20-70 kcal mol-1. Further examination of the coordination of the substrate molecules to Lewis acids of varying Lewis acid strengths resulted in a direct linear correlation between the ability of the Lewis acid-substrate adduct to accept a hydride and the Lewis acid strength. The linear correlations also revealed that between 44 and 70% of the Lewis acidity of the Lewis acids translated to the Lewis acid-substrate adducts. From the results obtained in this study, the minimum Lewis acid strength needed to activate the substrates for the reduction with [BH4]-and the implications of employing a Lewis acid to pr...Continue Reading

References

Oct 10, 2002·Chemical Reviews·Avelino Corma, Hermenegildo García
Apr 1, 2003·Journal of Computational Chemistry·Maurizio CossiVincenzo Barone
Nov 13, 2003·Chemical Reviews·Avelino Corma, Hermenegildo García
May 18, 2004·Chemistry : a European Journal·R Morris Bullock
Sep 17, 2009·Journal of the American Chemical Society·Michael T MockDaniel L DuBois
Apr 20, 2011·Chemical Communications : Chem Comm·Zachariah M Heiden, Douglas W Stephan
Oct 31, 2012·Chemistry, an Asian Journal·Sina SchwendemannGerhard Erker
Apr 21, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·A Paige Lathem, Zachariah M Heiden
Jul 12, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Benjamin L RinneZachariah M Heiden

❮ Previous
Next ❯

Citations

Jun 25, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Levente G PapElliott Hulley
Aug 12, 2020·Chemical Society Reviews·Kelsey R BreretonAlexander J M Miller
Apr 3, 2019·Tetrahedron·Brena L Thompson, Zachariah M Heiden
Apr 29, 2021·Physical Chemistry Chemical Physics : PCCP·Brena L Thompson, Zachariah M Heiden

❮ Previous
Next ❯

Software Mentioned

Gaussian

Related Concepts

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.

Related Papers

Dalton Transactions : an International Journal of Inorganic Chemistry
A Paige Lathem, Zachariah M Heiden
Dalton Transactions : an International Journal of Inorganic Chemistry
Benjamin L RinneZachariah M Heiden
Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
Céline Chizallet, Pascal Raybaud
© 2022 Meta ULC. All rights reserved