Computational Study on the Acidic Constants of Chiral Brønsted Acids in Dimethyl Sulfoxide

2014 ◽  
Vol 79 (10) ◽  
pp. 4340-4351 ◽  
Author(s):  
Chen Yang ◽  
Xiao-Song Xue ◽  
Xin Li ◽  
Jin-Pei Cheng
Keyword(s):  
Dimethyl Sulfoxide ◽  
Computational Study ◽  
Bronsted Acids ◽  
Chiral Brønsted Acids ◽  
Acidic Constants

Enantioselective oxysulfenylation and oxyselenenylation of olefins catalyzed by chiral Brønsted acids

Tetrahedron ◽  
2012 ◽  
Vol 68 (12) ◽  
pp. 2728-2735 ◽  
Author(s):  
Huan Guan ◽  
Haining Wang ◽  
Deshun Huang ◽  
Yian Shi
Keyword(s):  
Bronsted Acids ◽  
Chiral Brønsted Acids

Chiral Brønsted Acids and Their Calcium Salts in Catalytic Asymmetric Mannich Reactions of Cyclic 1,3-Diketones

Synlett ◽  
2011 ◽  
Vol 2011 (03) ◽  
pp. 323-326 ◽  
Author(s):  
Magnus Rueping ◽  
Teerawut Bootwicha ◽  
Erli Sugiono
Keyword(s):  
Bronsted Acids ◽  
Mannich Reactions ◽  
Calcium Salts ◽  
Catalytic Asymmetric ◽  
Chiral Brønsted Acids

scholarly journals H–Abstraction from Dimethyl Sulfide in the Presence of an Excess of Hydroxyl Radicals. A Quantum Chemical Evaluation of Thermochemical and Kinetic Parameters Unveil an Alternative Pathway to Dimethyl Sulfoxide.

2020 ◽  
Author(s):  
Zoi Salta ◽  
Jacopo Lupi ◽  
Vincenzo Barone ◽  
Oscar Ventura
Keyword(s):  
Dimethyl Sulfoxide ◽  
Hydroxyl Radicals ◽  
Quantum Chemical ◽  
Dimethyl Sulfide ◽  
Computational Study ◽  
Alternative Pathway ◽  
Oxidation Mechanism ◽  
State Theory ◽  
Rate Coefficients ◽  
Reduced Sulfur Compounds

<div> Elucidation of the oxidation mechanism of naturally emitted reduced sulfur compounds, especially dimethyl sulfide, plays a central role in understanding background acid precipitation in the natural environment. Most frequently, theoretical studies of the addition and H-elimination reactions of dimethyl sulfide with hydroxyl radicals are studied considering the presence of oxygen that further reacts with the radicals formed in the initial steps. Although the reaction of intermediate species with additional hydroxyl radicals has been considered as part of the global mechanism of oxidation, few if any attention has been dedicated to the possibility of reactions of the initial radicals with a second •OH molecule. In this work we performed a computational study using quantum-chemical methods, of the mechanism of H-abstraction from dimethyl sulfide under normal atmospheric conditions and in reaction chambers at different O2 partial pressure, including complete absence of oxygen. Additionally, important rate coefficients were computed using canonical and variational transition state theory. The rate coefficient for abstraction affords a 4.72 x 10-12 cm3 molecule1 s-1 value, very close to the most recent experimental one (4.13 x 10-12 cm3 molecule-1 s-1). According to our best results, the initial methyl thiomethyl radical was obtained at -25.2 kcal/mol (experimentally -22.4 kcal/mol), and four important paths were identified on the potential energy surface. From the interplay of thermochemical and kinetic arguments, it was possible to demonstrate that the preferred product of the reaction of dimethyl sulfide with two hydroxyl radicals, is actually dimethyl sulfoxide. </div><div> </div>

Highly Efficient AsymmetricTrans-Selective Aziridination of Diazoacetamides andN-Boc-imines Catalyzed by Chiral Brønsted Acids

2009 ◽  
Vol 11 (14) ◽  
pp. 3036-3039 ◽  
Author(s):  
Xiaofei Zeng ◽  
Xin Zeng ◽  
Zhenjiang Xu ◽  
Min Lu ◽  
Guofu Zhong
Keyword(s):  
Bronsted Acids ◽  
Highly Efficient ◽  
Chiral Brønsted Acids

Asymmetric protonation of lithium enolates of α-amino acid derivatives with α-amino acid-based chiral Brønsted acids

2003 ◽  
pp. 566 ◽  
Author(s):  
Kentaro Futatsugi ◽  
Akira Yanagisawa ◽  
Hisashi Yamamoto
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Bronsted Acids ◽  
Lithium Enolates ◽  
Chiral Brønsted Acids

Chiral Brønsted Acids for Asymmetric Organocatalysis

2009 ◽  
pp. 395-456 ◽  
Author(s):  
Daniela Kampen ◽  
Corinna M. Reisinger ◽  
Benjamin List
Keyword(s):  
Bronsted Acids ◽  
Asymmetric Organocatalysis ◽  
Chiral Brønsted Acids

Highly Enantioselective Friedel-Crafts Reaction of 4,7-Dihydroindoles with β,γ-Unsaturated α-Keto Esters by Chiral Brønsted Acids

2008 ◽  
Vol 350 (14-15) ◽  
pp. 2169-2173 ◽  
Author(s):  
Mi Zeng ◽  
Qiang Kang ◽  
Qing-Li He ◽  
Shu-Li You
Keyword(s):  
Bronsted Acids ◽  
Keto Esters ◽  
Chiral Brønsted Acids

scholarly journals Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids

2017 ◽  
Vol 8 (10) ◽  
pp. 7197-7202 ◽  
Author(s):  
Guo-Peng Wang ◽  
Meng-Qing Chen ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Proton Transfer ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Bronsted Acids ◽  
Bronsted Acid ◽  
Nazarov Cyclization ◽  
Cooperative Catalysis ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid ◽  
Chiral Brønsted Acids

The first enantioselective Nazarov cyclization of substrates with only one coordinating site and with proton-transfer as an enantioselective-determining step was realized by means of cooperative catalysis with a Lewis acid and a chiral Brønsted acid.

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