Several organosulfur compounds are present in the crude oil, and are required to be removed before its processing into transport fuel. For this reason, biodesulfurization of thiophenic compounds has been studied extensively. However, studies on the sulfide compounds are scarce. In this paper, we describe desulfurization of a model sulfidic compound, dibenzyl sulfide (DBS) by an isolated Gordonia sp. IITR100. The reaction was accompanied with the formation of metabolites dibenzyl sulfoxide, dibenzyl sulfone and benzoic acid. Studies with recombinant E. coli revealed that enzyme DszC of this isolate metabolizes DBS into dibenzyl sulfoxide and dibenzyl sulfone, but the reaction downstream to it is mediated by some enzyme other than its DszA. In reactions where DBS and dibenzothiophene (DBT) were present together, both IITR100 and recombinant E. coli exhibited preference for the desulfurization of DBS over DBT. The newly identified capability of IITR100 for desulfurization of both thiophenic and sulfidic compounds suggests its potential use in improved desulfurization of petroleum fractions.
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http://dx.doi.org/10.1007/s13205-014-0221-1 | DOI Listing |
J Org Chem
October 2024
Faculty of Pharmacy, Musashino University, 1-1-20 Shinmachi Nishitokyo, Tokyo 202-8585, Japan.
This study demonstrated for the first time that alkenoic thioesters can be effectively used as nucleophiles in ring-closing disulfenylation reactions. Our investigation revealed that the reaction in hexafluoroisopropanol with an electrophilic sulfur reagent significantly enhances the product yield. We gathered experimental and theoretical evidence to support the superiority of thioesters over the traditionally used benzyl sulfide.
View Article and Find Full Text PDFOrg Lett
October 2024
Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, China.
A coupling reaction between diazo compounds and phenyl benzyl sulfide catalyzed by TfOH has been reported. This reaction can synthesize important α-arylthio carbonyl compounds via regioselective cleavage and reconfiguration of C-S bonds, and various functional groups were tolerant to the reaction conditions. Mechanistic studies have conclusively established that the pivotal intermediate in the reaction was meticulously investigated through spectroscopic evidence, complemented by rigorous control experiments.
View Article and Find Full Text PDFChem Asian J
January 2023
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences (CAS), North First Street 2, 100190, Beijing, P. R. China).
Benzyl phenyl sulfide is a kind of important chemicals with wide usage, which is mainly prepared through a nucleophilic reaction of thiophenol with benzyl chlorides or benzyl alcohols, suffering from inherent drawbacks, such as low efficiency, requirements for equivalent acid or base catalysts and formation of harmful byproducts and waste. Herein, we report a green route to access various benzyl phenyl sulfide derivatives in good to excellent yields under mild conditions via the reaction of thioanisoles with benzyl alcohols over ionic liquid 1-propylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO HPrMIm][OTf]). Mechanism investigation indicates that the synergic effect of cation and anion of [SO HPrMIm][OTf] activates thioanisoles and benzyl alcohols via hydrogen bonding, thus catalyzes the dehydration of benzyl alcohol to dibenzyl ether and the subsequent metathesis reaction between dibenzyl ether and benzyl phenyl sulfide, finally generating benzyl phenyl sulfide derivatives.
View Article and Find Full Text PDFInt J Mol Sci
February 2022
State Key Laboratory of Power Transmission Equipment & System Security and New Technology, Chongqing University, Chongqing 400044, China.
The vibration spectroscopy (Raman and infrared) of widely concerned molecules in sulfur corrosion phenomenon (Dibenzyl Disulfide, Dibenzyl Sulphide, and Bibenzyl) is detailedly analyzed based on density functional theory and experimental measurement. The dominant conformations of these molecules are determined according to Boltzmann distribution in relative Gibbs free energy. Additionally, noncovalent interaction analysis is conducted to indicate intramolecular interaction.
View Article and Find Full Text PDFChem Commun (Camb)
May 2020
Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
An ambident electrophilicity of phosphinic acid thioesters is disclosed. Unexpected carbon-sulfur bond formation took place in the reaction between phosphinic acid thioesters and benzyl Grignard reagents. The developed method for benzyl sulfides has a wide substrate scope and was applicable for the synthesis of a drug analog.
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