Thermodynamic and kinetic studies of hydride transfer from Hantzsch ester under the promotion of organic bases‡
Literature Information
Zhen Li, Jin-Dong Yang, Jin-Pei Cheng
Base-promoted hydride transfer (BPHyT), a strategy for the upconversion of hydride donors, was studied here in a three-component system, composed of Hantzsch ester (HEH), acridinium derivatives and organic bases. Based on the thermodynamic parameters of hydricity and pKa, we proposed a thermodynamic cycle to evaluate the apparent hydricity of HEH/base combinations, as well as the overall driving force of BPHyT. Brønsted-type linear analysis indicated that the base used in BPHyT is much more effective to regulate the reaction kinetics, compared to conventional Brønsted acid or base catalysis. Structure–reactivity relationships showed that the hydride acceptor and the base contribute equally to regulate the kinetics of BPHyT. Kinetic isotope effects suggested that the hydride transfer is involved in the rate-determining step. Reductions of the polar CC bonds by HEH/base combinations were performed to confirm the feasibility of applying BPHyT in organic synthesis.
Related Literature
Single-wall carbon nanotubes and peapods investigated by EPR
B. Corzilius, K.-P. Dinse, K. Hata
DOI: 10.1039/B707936M
Performance of spin-component-scaled Møller–Plesset theory (SCS-MP2) for potential energy curves of noncovalent interactions
Tait Takatani
DOI: 10.1039/B709669K
Synthesis, characterization, and intracellular uptake of carboxyl-terminated poly(amidoamine) dendrimer-stabilized iron oxide nanoparticles
Xiangyang Shi, Thommey P. Thomas, Lukasz A. Myc, Alina Kotlyar, James R. Baker, Jr
DOI: 10.1039/B709147H
The canonical and other mechanisms of elementary chemical reactions
Jesús Aldegunde, F. Javier Aoiz, Vicente Sáez-Rábanos, Brian K. Kendrick, Marcelo P. de Miranda
DOI: 10.1039/B707190F
Dissociative electron attachment to gas phase glycine: Exploring the decomposition pathways by mass separation of isobaric fragment anions
A. Mauracher, S. Denifl, A. Aleem, N. Wendt, F. Zappa, P. Cicman, M. Probst, T. D. Märk, P. Scheier, H. D. Flosadóttir, O. Ingólfsson, E. Illenberger
DOI: 10.1039/B709140K
Investigation of the interactions between alkanethiol self-assembled monolayers and a liquid overlayer using impedance spectroscopy
Janelle D. S. Newman, G. J. Blanchard
DOI: 10.1039/B711212B
Potential energy surface for cyclotrimethylene trinitramine dimer from symmetry-adapted perturbation theory‡
Robert Bukowski, Betsy M. Rice
DOI: 10.1039/B709192C
On the position of the potential wall in DFT temporary anion calculations
Nick Sablon, Frank De Proft, Paul Geerlings, David J. Tozer
DOI: 10.1039/B711428A
You might also like
What is Ethyl 3-cyclohexylpropanoate (CAS: 10094-36-7)?
Ethyl 3-cyclohexylpropanoate is a clear, colorless to light yellow liquid with a...
How should waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)nicotinic acid (CAS: 34783-31-8) be handled?
Waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl...
How should waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) be handled?
Waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) sho...
What precautions should be taken when handling Chloroac-nle-oh (CAS: 56787-36-1)?
When handling Chloroac-nle-oh (CAS: 56787-36-1), it is essential to wear appropr...
What industries use Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 752244-05-6)?
Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate is primarily used in the...
Are there alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis?
Alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis ...
How should waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) be handled?
Waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) should be managed...
What industries use 1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9)?
1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9) is used in various ...
Are there alternatives to 3-Bromo-5-(N-Boc)aminomethylisoxazole (CAS: 903131-45-3) in synthesis?
There are alternative reagents and compounds that can be used in the synthesis o...
What is Tungsten(IV) oxide (CAS: 12036-22-5)?
Tungsten(IV) oxide, also known as tungsten dioxide, is a chemical compound with ...
Source Journal
Organic Chemistry Frontiers

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry














