A DFT examination of the role of proximal boron functionalities in the S-alkylation of sulfenic acid anions

2022 ◽  
Author(s):  
Andrew G. Durant ◽  
Eric A. Nicol ◽  
Brandon M. McInnes ◽  
Adrian L. Schwan
Keyword(s):  
Reaction Site ◽  
Sulfenic Acid ◽  
Alkylation Reactions ◽  
Dft Modelling

DFT modelling predicts proximal boron groups can accelerate sulfenate alkylation reactions, depending on boron substituents and boron distance from the reaction site.

A Fast and Additive Free C-C Homo/Cross-Coupling Reaction in Reverse Micelle: An Understanding of Role of Surfactant, Water Content and Base on the Product Yield and Reaction Site

2017 ◽  
Vol 2 (3) ◽  
pp. 1079-1088 ◽  
Author(s):  
Barnali Kar ◽  
Soumik Bardhan ◽  
Prasanjit Ghosh ◽  
Bhaskar Ganguly ◽  
Kaushik Kundu ◽  
...  
Keyword(s):  
Water Content ◽  
Reverse Micelle ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Product Yield ◽  
Reaction Site ◽  
Cross Coupling Reaction

scholarly journals The pivotal function of dehydroascorbate reductase in glutathione homeostasis in plants

2020 ◽  
Vol 71 (12) ◽  
pp. 3405-3416 ◽  
Author(s):  
Haiyan Ding ◽  
Bipeng Wang ◽  
Yi Han ◽  
Shengchun Li
Keyword(s):  
Reduced Form ◽  
Glutathione S Transferase ◽  
Sulfenic Acid ◽  
Abiotic And Biotic Stresses ◽  
Biotic Stresses ◽  
Ping Pong ◽  
Rapid Changes ◽  
Catalytic Cysteine ◽  
Oxidation Analysis

Abstract Under natural conditions, plants are exposed to various abiotic and biotic stresses that trigger rapid changes in the production and removal of reactive oxygen species (ROS) such as hydrogen peroxide (H2O2). The ascorbate-glutathione pathway has been recognized to be a key player in H2O2 metabolism, in which reduced glutathione (GSH) regenerates ascorbate by reducing dehydroascorbate (DHA), either chemically or via DHA reductase (DHAR), an enzyme belonging to the glutathione S-transferase (GST) superfamily. Thus, DHAR has been considered to be important in maintaining the ascorbate pool and its redox state. Although some GSTs and peroxiredoxins may contribute to GSH oxidation, analysis of Arabidopsis dhar mutants has identified the key role of DHAR in coupling H2O2 to GSH oxidation. The reaction of DHAR has been proposed to proceed by a ping-pong mechanism, in which binding of DHA to the free reduced form of the enzyme is followed by binding of GSH. Information from crystal structures has shed light on the formation of sulfenic acid at the catalytic cysteine of DHAR that occurs with the reduction of DHA. In this review, we discuss the molecular properties of DHAR and its importance in coupling the ascorbate and glutathione pools with H2O2 metabolism, together with its functions in plant defense, growth, and development.

Substituent Effect on Reactivity of Alkyl Thiolacetates

1971 ◽  
Vol 26 (7) ◽  
pp. 703-707
Author(s):  
F. Dutka ◽  
A. F. Márton ◽  
P. Vinkler
Keyword(s):  
Chemical Reaction ◽  
Sulfur Atom ◽  
Substituent Effect ◽  
Linear Structure ◽  
Common Mechanism ◽  
Reaction Site ◽  
Structure Reactivity Relationship ◽  
Kinetics Of

Kinetics of catalyzed acyl group exchange between acetic-1-14C anhydride and alkyl thiolacetates was investigated. The exchange is not accompanied by chemical reaction and demonstrates the full equivalency of anhydride acyl groups in the process. The rate of exchange is lowered by increasing branching rather than lengthening in S-alkyl substituents. The role of catalyst and structures of possible intermediates are interpreted. Upon existing linear structure-reactivity relationship a common mechanism involving sulfur atom as the reaction site seems to be operative.

Synthesis of Fluorinated Acridines via Sequential Micellar Buchwald–Hartwig Amination/Cyclization of Aryl Bromides

Synthesis ◽  
2018 ◽  
Vol 50 (08) ◽  
pp. 1621-1628 ◽  
Author(s):  
Luca Beverina ◽  
Luca Vaghi ◽  
Alessandro Sanzone ◽  
Mauro Sassi ◽  
Simone Pagani ◽  
...  
Keyword(s):  
Reaction Site ◽  
Aryl Bromides

Fluorinated unsymmetrical acridines are efficiently prepared by means of a tandem micellar Buchwald–Hartwig amination followed by an acid-promoted cyclization. The overall process is advantageous with respect to previously described protocols both in terms of efficiency and sustainability. The role of the cosolvent in the amination step is highlighted, demonstrating that rather than resorting to highly expensive catalysts, Buchwald–Hartwig aminations can be straightforwardly carried out by tuning the reaction site polarity.

scholarly journals The Role of Neutral and Radical Anionic Organozinc Complexes in the Alkylation Reactions of 1,4-Diaza-1,3-butadienes with Diorganozinc Compounds†

1997 ◽  
Vol 16 (14) ◽  
pp. 3158-3164 ◽  
Author(s):  
Evelien Rijnberg ◽  
Jaap Boersma ◽  
Johann T. B. H. Jastrzebski ◽  
Miles T. Lakin ◽  
Anthony L. Spek ◽  
...  
Keyword(s):  
Alkylation Reactions

Inactivation of Intracellular Thioldependent Enzymes by HOSCN: Evidence for a Role of Sulfenic Acid Intermediates

2010 ◽  
Vol 49 ◽  
pp. S166
Author(s):  
Tessa J Barrett ◽  
David I Pattison ◽  
Michael J Davies ◽  
Clare L Hawkins
Keyword(s):  
Sulfenic Acid
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