FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W3174085816> ?p ?o ?g. }

• W3174085816 endingPage "10156" @default.
• W3174085816 startingPage "10143" @default.
• W3174085816 abstract "Boron-containing heterocycles are important in a variety of applications from drug discovery to materials science; therefore a clear understanding of their structure and reactivity is desirable to optimize these functions. Although the boranol (B-OH) unit of boronic acids behaves as a Lewis acid to form a tetravalent trihydroxyborate conjugate base, it has been proposed that pseudoaromatic hemiboronic acids may possess sufficient aromatic character to act as Brønsted acids and form a boron oxy conjugate base, thereby avoiding the disruption of ring aromaticity that would occur with a tetravalent boronate anion. Until now no firm evidence existed to ascertain the structure of the conjugate base and the aromatic character of the boron-containing ring of hemiboronic naphthoid isosteres. Here, these questions are addressed with a combination of experimental, spectroscopic, X-ray crystallographic, and computational studies of a series of model benzoxazaborine and benzodiazaborine naphthoids. Although these hemiboronic heterocycles are unambiguously shown to behave as Lewis acids in aqueous solutions, boraza derivatives possess partial aromaticity provided their nitrogen lone electron pair is sufficiently available to participate in extended delocalization. As demonstrated by dynamic exchange and crossover experiments, these heterocycles are stable in neutral aqueous medium, and their measured pKa values are consistent with the ability of the endocyclic heteroatom substituent to stabilize a partial negative charge in the conjugate base. Altogether, this study corrects previous inaccuracies and provides conclusions regarding the properties of these compounds that are important toward the methodical application of hemiboronic and other boron heterocycles in catalysis, bioconjugation, and medicinal chemistry." @default.
• W3174085816 created "2021-07-05" @default.
• W3174085816 creator A5009925446 @default.
• W3174085816 creator A5016425697 @default.
• W3174085816 creator A5023415427 @default.
• W3174085816 creator A5036019142 @default.
• W3174085816 creator A5045248437 @default.
• W3174085816 creator A5078317759 @default.
• W3174085816 creator A5078764952 @default.
• W3174085816 date "2021-06-24" @default.
• W3174085816 modified "2023-10-06" @default.
• W3174085816 title "Lewis or Brønsted? A Rectification of the Acidic and Aromatic Nature of Boranol-Containing Naphthoid Heterocycles" @default.
• W3174085816 cites W1260922102 @default.
• W3174085816 cites W1498365154 @default.
• W3174085816 cites W1753489606 @default.
• W3174085816 cites W1965011444 @default.
• W3174085816 cites W1968310807 @default.
• W3174085816 cites W1987905567 @default.
• W3174085816 cites W1989765623 @default.
• W3174085816 cites W2000875788 @default.
• W3174085816 cites W2006941404 @default.
• W3174085816 cites W2007933863 @default.
• W3174085816 cites W2010621614 @default.
• W3174085816 cites W2011453303 @default.
• W3174085816 cites W2026172453 @default.
• W3174085816 cites W2030545256 @default.
• W3174085816 cites W2037667906 @default.
• W3174085816 cites W2053248916 @default.
• W3174085816 cites W2070370255 @default.
• W3174085816 cites W2075290468 @default.
• W3174085816 cites W2089432886 @default.
• W3174085816 cites W2091929113 @default.
• W3174085816 cites W2093360044 @default.
• W3174085816 cites W2095517944 @default.
• W3174085816 cites W2112775392 @default.
• W3174085816 cites W2137631747 @default.
• W3174085816 cites W2152933949 @default.
• W3174085816 cites W2240530019 @default.
• W3174085816 cites W2241225072 @default.
• W3174085816 cites W2275894450 @default.
• W3174085816 cites W2313658489 @default.
• W3174085816 cites W2321612681 @default.
• W3174085816 cites W2325302768 @default.
• W3174085816 cites W2327177546 @default.
• W3174085816 cites W2332391293 @default.
• W3174085816 cites W2334892113 @default.
• W3174085816 cites W2345914391 @default.
• W3174085816 cites W2470053394 @default.
• W3174085816 cites W2586053703 @default.
• W3174085816 cites W2613680293 @default.
• W3174085816 cites W2742917280 @default.
• W3174085816 cites W2783161192 @default.
• W3174085816 cites W2829757150 @default.
• W3174085816 cites W2949276763 @default.
• W3174085816 cites W2949546387 @default.
• W3174085816 cites W2955791106 @default.
• W3174085816 cites W3017959452 @default.
• W3174085816 cites W3135153012 @default.
• W3174085816 doi "https://doi.org/10.1021/jacs.1c02462" @default.
• W3174085816 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/34165966" @default.
• W3174085816 hasPublicationYear "2021" @default.
• W3174085816 type Work @default.
• W3174085816 sameAs 3174085816 @default.
• W3174085816 citedByCount "13" @default.
• W3174085816 countsByYear W31740858162021 @default.
• W3174085816 countsByYear W31740858162022 @default.
• W3174085816 countsByYear W31740858162023 @default.
• W3174085816 crossrefType "journal-article" @default.
• W3174085816 hasAuthorship W3174085816A5009925446 @default.
• W3174085816 hasAuthorship W3174085816A5016425697 @default.
• W3174085816 hasAuthorship W3174085816A5023415427 @default.
• W3174085816 hasAuthorship W3174085816A5036019142 @default.
• W3174085816 hasAuthorship W3174085816A5045248437 @default.
• W3174085816 hasAuthorship W3174085816A5078317759 @default.
• W3174085816 hasAuthorship W3174085816A5078764952 @default.
• W3174085816 hasConcept C134306372 @default.
• W3174085816 hasConcept C142724271 @default.
• W3174085816 hasConcept C145148216 @default.
• W3174085816 hasConcept C147597530 @default.
• W3174085816 hasConcept C161790260 @default.
• W3174085816 hasConcept C163638829 @default.
• W3174085816 hasConcept C178790620 @default.
• W3174085816 hasConcept C181199279 @default.
• W3174085816 hasConcept C185592680 @default.
• W3174085816 hasConcept C192386470 @default.
• W3174085816 hasConcept C197336794 @default.
• W3174085816 hasConcept C204787440 @default.
• W3174085816 hasConcept C20950531 @default.
• W3174085816 hasConcept C21951064 @default.
• W3174085816 hasConcept C2776793192 @default.
• W3174085816 hasConcept C2776910235 @default.
• W3174085816 hasConcept C2777864310 @default.
• W3174085816 hasConcept C2777992278 @default.
• W3174085816 hasConcept C2778689049 @default.
• W3174085816 hasConcept C2780378348 @default.
• W3174085816 hasConcept C32909587 @default.
• W3174085816 hasConcept C33923547 @default.
• W3174085816 hasConcept C46000676 @default.

• next