Matches in SemOpenAlex for { <https://semopenalex.org/work/W2037085893> ?p ?o ?g. }
- W2037085893 endingPage "4684" @default.
- W2037085893 startingPage "4674" @default.
- W2037085893 abstract "Stability constants of boronic acid diol esters in aqueous solution have been determined potentiometrically for a series of meta-, para-substituted phenylboronic acids and diols of variable acidity. The constants β11-1 for reactions between neutral forms of reactants producing the anionic ester plus proton follow the Hammett equation with ρ depending on pKa of diol and varying from 2.0 for glucose to 1.29 for 4-nitrocatechol. Observed stability constants (Kobs) measured by UV–vis and fluorometric titrations at variable pH for esters of 4,5-dihydroxy-1,3-benzenedisulfonate (Tiron) generally agree with those expected on the basis of β11-1 values, but the direct fitting of Kobs vs pH profiles gives shifted pKa values both for boronic acids and diol as a result of significant interdependence of fitting parameters. The subsituent effects on absorption and fluorescence spectra of Tiron arylboronate esters are characterized. The Kobs for Tiron determined by 11B NMR titrations are approximately 1 order of magnitude smaller than those determined by UV–vis titrations under identical conditions. A general equation, which makes possible an estimate of β11-1 for any pair of boronic acid and diol from their pKa values, is proposed on the basis of established Brönsted-type correlation of Hammett parameters for β11-1 with acidity of diols. The equation allows one to calculate stability constants expected only on basis of acid–base properties of the components, thus permitting more strict evaluation of contributions of additional factors such as steric or charge effects to the ester stability." @default.
- W2037085893 created "2016-06-24" @default.
- W2037085893 creator A5023467561 @default.
- W2037085893 creator A5045829422 @default.
- W2037085893 creator A5063724899 @default.
- W2037085893 creator A5091529193 @default.
- W2037085893 date "2013-05-02" @default.
- W2037085893 modified "2023-10-04" @default.
- W2037085893 title "Substituent Effects and pH Profiles for Stability Constants of Arylboronic Acid Diol Esters" @default.
- W2037085893 cites W1979939682 @default.
- W2037085893 cites W1983223629 @default.
- W2037085893 cites W1987715285 @default.
- W2037085893 cites W1991527689 @default.
- W2037085893 cites W1993703556 @default.
- W2037085893 cites W1996323804 @default.
- W2037085893 cites W2001910387 @default.
- W2037085893 cites W2007838251 @default.
- W2037085893 cites W2007933863 @default.
- W2037085893 cites W2008096428 @default.
- W2037085893 cites W2012675110 @default.
- W2037085893 cites W2015700034 @default.
- W2037085893 cites W2019587160 @default.
- W2037085893 cites W2024768627 @default.
- W2037085893 cites W2028881531 @default.
- W2037085893 cites W2034530919 @default.
- W2037085893 cites W2036607554 @default.
- W2037085893 cites W2036967221 @default.
- W2037085893 cites W2044529613 @default.
- W2037085893 cites W2062938584 @default.
- W2037085893 cites W2067436522 @default.
- W2037085893 cites W2067906450 @default.
- W2037085893 cites W2070684772 @default.
- W2037085893 cites W2075290468 @default.
- W2037085893 cites W2076976762 @default.
- W2037085893 cites W2080778401 @default.
- W2037085893 cites W2085381403 @default.
- W2037085893 cites W2086184134 @default.
- W2037085893 cites W2088122376 @default.
- W2037085893 cites W2106527539 @default.
- W2037085893 cites W2113561474 @default.
- W2037085893 cites W2137890605 @default.
- W2037085893 cites W2138520198 @default.
- W2037085893 cites W2152649528 @default.
- W2037085893 cites W2158142220 @default.
- W2037085893 cites W2159863025 @default.
- W2037085893 cites W2164875595 @default.
- W2037085893 cites W2171219272 @default.
- W2037085893 cites W2313658489 @default.
- W2037085893 cites W2317206726 @default.
- W2037085893 cites W2951119274 @default.
- W2037085893 cites W416990685 @default.
- W2037085893 cites W4214597346 @default.
- W2037085893 cites W4241445517 @default.
- W2037085893 cites W4301973482 @default.
- W2037085893 doi "https://doi.org/10.1021/jo400617j" @default.
- W2037085893 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23631757" @default.
- W2037085893 hasPublicationYear "2013" @default.
- W2037085893 type Work @default.
- W2037085893 sameAs 2037085893 @default.
- W2037085893 citedByCount "73" @default.
- W2037085893 countsByYear W20370858932013 @default.
- W2037085893 countsByYear W20370858932014 @default.
- W2037085893 countsByYear W20370858932015 @default.
- W2037085893 countsByYear W20370858932016 @default.
- W2037085893 countsByYear W20370858932017 @default.
- W2037085893 countsByYear W20370858932018 @default.
- W2037085893 countsByYear W20370858932019 @default.
- W2037085893 countsByYear W20370858932020 @default.
- W2037085893 countsByYear W20370858932021 @default.
- W2037085893 countsByYear W20370858932022 @default.
- W2037085893 countsByYear W20370858932023 @default.
- W2037085893 crossrefType "journal-article" @default.
- W2037085893 hasAuthorship W2037085893A5023467561 @default.
- W2037085893 hasAuthorship W2037085893A5045829422 @default.
- W2037085893 hasAuthorship W2037085893A5063724899 @default.
- W2037085893 hasAuthorship W2037085893A5091529193 @default.
- W2037085893 hasConcept C121332964 @default.
- W2037085893 hasConcept C145148216 @default.
- W2037085893 hasConcept C148898269 @default.
- W2037085893 hasConcept C155647269 @default.
- W2037085893 hasConcept C161790260 @default.
- W2037085893 hasConcept C168191866 @default.
- W2037085893 hasConcept C178790620 @default.
- W2037085893 hasConcept C181199279 @default.
- W2037085893 hasConcept C184651966 @default.
- W2037085893 hasConcept C184866935 @default.
- W2037085893 hasConcept C185592680 @default.
- W2037085893 hasConcept C201194858 @default.
- W2037085893 hasConcept C22163223 @default.
- W2037085893 hasConcept C2777734296 @default.
- W2037085893 hasConcept C2777864310 @default.
- W2037085893 hasConcept C2778689049 @default.
- W2037085893 hasConcept C2779515768 @default.
- W2037085893 hasConcept C2780795997 @default.
- W2037085893 hasConcept C2781330165 @default.
- W2037085893 hasConcept C30095370 @default.
- W2037085893 hasConcept C62520636 @default.
- W2037085893 hasConcept C8503813 @default.