FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2968353584> ?p ?o ?g. }

• W2968353584 endingPage "4779" @default.
• W2968353584 startingPage "4775" @default.
• W2968353584 abstract "Abstract The nucleophilic and reductive properties of thiolates and thiols make them ideal candidates as redox mediators via the thiol/disulfide couple. One mechanism for biological lignin depolymerization entails reduction of keto aryl ether bonds by an S N 2 mechanism with the thiol redox mediator glutathione. In this study, mimicking this chemistry in a simple protein‐ and metal‐free process, several small organic thiols are surveyed for their ability to cleave aryl keto ethers that model the β‐ O ‐4 linkages found in partially oxidized lignin. In polar aprotic solvents, β‐mercaptoethanol and dithiothreitol yielded up to 100 % formation of phenol and acetophenone products from 2‐phenoxyacetophenone, but not from its reduced alcohol congener. The effects of reaction conditions and of substituents on the aryl rings and the keto ether linkage are assessed. These results, together with activation barriers computed by quantum chemical simulations and direct observation of the expected intermediate thioether, point to an S N 2 mechanism. This study confirms that small organic thiols can reductively break down lignin‐relevant keto aryl ether linkages." @default.
• W2968353584 created "2019-08-22" @default.
• W2968353584 creator A5001291968 @default.
• W2968353584 creator A5015483238 @default.
• W2968353584 creator A5019236643 @default.
• W2968353584 creator A5035163747 @default.
• W2968353584 creator A5040774017 @default.
• W2968353584 creator A5079481609 @default.
• W2968353584 creator A5086130594 @default.
• W2968353584 date "2019-09-11" @default.
• W2968353584 modified "2023-10-14" @default.
• W2968353584 title "Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols" @default.
• W2968353584 cites W1982811967 @default.
• W2968353584 cites W1984865044 @default.
• W2968353584 cites W1989761868 @default.
• W2968353584 cites W2015260661 @default.
• W2968353584 cites W2048421344 @default.
• W2968353584 cites W2086635150 @default.
• W2968353584 cites W2111886847 @default.
• W2968353584 cites W2125653280 @default.
• W2968353584 cites W2134967712 @default.
• W2968353584 cites W2150299360 @default.
• W2968353584 cites W2153154728 @default.
• W2968353584 cites W2264004717 @default.
• W2968353584 cites W2295090549 @default.
• W2968353584 cites W2316355312 @default.
• W2968353584 cites W2318301891 @default.
• W2968353584 cites W2318985750 @default.
• W2968353584 cites W2322372984 @default.
• W2968353584 cites W2441046938 @default.
• W2968353584 cites W2441647337 @default.
• W2968353584 cites W2465196018 @default.
• W2968353584 cites W2608588862 @default.
• W2968353584 cites W2770114257 @default.
• W2968353584 cites W2783757378 @default.
• W2968353584 cites W2786479777 @default.
• W2968353584 cites W2900116919 @default.
• W2968353584 cites W2904069367 @default.
• W2968353584 doi "https://doi.org/10.1002/cssc.201901742" @default.
• W2968353584 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/31418534" @default.
• W2968353584 hasPublicationYear "2019" @default.
• W2968353584 type Work @default.
• W2968353584 sameAs 2968353584 @default.
• W2968353584 citedByCount "21" @default.
• W2968353584 countsByYear W29683535842020 @default.
• W2968353584 countsByYear W29683535842021 @default.
• W2968353584 countsByYear W29683535842022 @default.
• W2968353584 countsByYear W29683535842023 @default.
• W2968353584 crossrefType "journal-article" @default.
• W2968353584 hasAuthorship W2968353584A5001291968 @default.
• W2968353584 hasAuthorship W2968353584A5015483238 @default.
• W2968353584 hasAuthorship W2968353584A5019236643 @default.
• W2968353584 hasAuthorship W2968353584A5035163747 @default.
• W2968353584 hasAuthorship W2968353584A5040774017 @default.
• W2968353584 hasAuthorship W2968353584A5079481609 @default.
• W2968353584 hasAuthorship W2968353584A5086130594 @default.
• W2968353584 hasConcept C161790260 @default.
• W2968353584 hasConcept C178790620 @default.
• W2968353584 hasConcept C178907741 @default.
• W2968353584 hasConcept C185592680 @default.
• W2968353584 hasConcept C2777329087 @default.
• W2968353584 hasConcept C2778815869 @default.
• W2968353584 hasConcept C2779444094 @default.
• W2968353584 hasConcept C2780263894 @default.
• W2968353584 hasConcept C2780407432 @default.
• W2968353584 hasConcept C2781076698 @default.
• W2968353584 hasConcept C2781324293 @default.
• W2968353584 hasConcept C49852136 @default.
• W2968353584 hasConcept C55904794 @default.
• W2968353584 hasConceptScore W2968353584C161790260 @default.
• W2968353584 hasConceptScore W2968353584C178790620 @default.
• W2968353584 hasConceptScore W2968353584C178907741 @default.
• W2968353584 hasConceptScore W2968353584C185592680 @default.
• W2968353584 hasConceptScore W2968353584C2777329087 @default.
• W2968353584 hasConceptScore W2968353584C2778815869 @default.
• W2968353584 hasConceptScore W2968353584C2779444094 @default.
• W2968353584 hasConceptScore W2968353584C2780263894 @default.
• W2968353584 hasConceptScore W2968353584C2780407432 @default.
• W2968353584 hasConceptScore W2968353584C2781076698 @default.
• W2968353584 hasConceptScore W2968353584C2781324293 @default.
• W2968353584 hasConceptScore W2968353584C49852136 @default.
• W2968353584 hasConceptScore W2968353584C55904794 @default.
• W2968353584 hasFunder F4320337393 @default.
• W2968353584 hasFunder F4320337509 @default.
• W2968353584 hasIssue "21" @default.
• W2968353584 hasLocation W29683535841 @default.
• W2968353584 hasLocation W29683535842 @default.
• W2968353584 hasLocation W29683535843 @default.
• W2968353584 hasOpenAccess W2968353584 @default.
• W2968353584 hasPrimaryLocation W29683535841 @default.
• W2968353584 hasRelatedWork W2026139859 @default.
• W2968353584 hasRelatedWork W2031526759 @default.
• W2968353584 hasRelatedWork W2071746505 @default.
• W2968353584 hasRelatedWork W2108467888 @default.
• W2968353584 hasRelatedWork W2952368810 @default.
• W2968353584 hasRelatedWork W2968353584 @default.
• W2968353584 hasRelatedWork W4241708406 @default.
• W2968353584 hasRelatedWork W4307943795 @default.

• next