Fluorinated Boronic Acids: Acidity and Hydrolytic Stability of Fluorinated Phenylboronic Acids

Zarzeczańska, Dorota; Adamczyk‐Woźniak, Agnieszka; Kulpa, Amanda; Ossowski, Tadeusz; Sporzyński, Andrzej

doi:10.1002/ejic.201700546

Cited by 30 publications

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References 32 publications

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“…Therefore the p K a values of compounds 1 and 2 have been determined by spectrophotometric methods and compared with the previously reported value for the para ‐isomer ( 3 ) . Similarly to other isomeric phenylboronic acids,, the position of the substituent influences the p K a value mostly for the meta isomer. In the case of the presence of the alkoxyl substituent (electron donating group) at the ortho ( 1 ) and para ( 3 ) positions a slight drop in acidity in comparison with the unsubstituted phenylboronic acid is observed.…”

Section: Resultsmentioning

confidence: 96%

Dehydration of ortho‐, meta‐ and para‐Alkoxy Phenylboronic Acids to their Corresponding Boroxines

et al. 2018

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Section: Resultsmentioning

confidence: 96%

Dehydration of ortho‐, meta‐ and para‐Alkoxy Phenylboronic Acids to their Corresponding Boroxines

et al. 2018

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“…According to expectations, the acidity of meta ( 2 ) and para ( 3 ) isomers is higher than that for the unsubstituted phenylboronic acid: their p K a values are ca. one unit lower than that of a parent PhB(OH) 2 , which is 8.8 [ 3 ]. This is due to the inductive effect of the -OCF 3 group, which in comparison with the trifluoromethyl substituent (-CF 3 group) is slightly diminished by the resonance effect of an oxygen atom.…”

Section: Resultsmentioning

confidence: 99%

“…The introduction of a fluorine atom directly to the aromatic ring or to its substituents usually increases the Lewis acidity of these compounds, which is important in terms of their applications as well as stability [ 2 ]. The literature on arylboronic compounds with fluorine substituents is quite extensive and covers such areas as: acidity of the compounds [ 3 , 4 ], structural studies [ 5 , 6 , 7 ], NMR characterization [ 7 , 8 ], or equilibria in solutions [ 9 , 10 , 11 ] as well as antimicrobial activity [ 10 , 11 ]. The extreme electronegativity of the fluorine substituent induces a strong withdrawing inductive effect, whereas the resonance effect of its lone-pair electrons allows the fluorine atom to be considered as a π-electron donor as well [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

(Trifluoromethoxy)Phenylboronic Acids: Structures, Properties, and Antibacterial Activity

et al. 2021

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Three isomers of (trifluoromethoxy)phenylboronic acids were studied in the context of their physicochemical, structural, antimicrobial and spectroscopic properties. They were characterized by 1H, 13C, 11B and 19F NMR spectroscopy. The acidity of all the isomers was evaluated by both spectrophotometric and potentiometric titrations. The introduction of the -OCF3 group influences the acidity, depending, however, on the position of a substituent, with the ortho isomer being the least acidic. Molecular and crystal structures of ortho and para isomers were determined by the single crystal XRD method. Hydrogen bonded dimers are the basic structural motives of the investigated molecules in the solid state. In the case of the ortho isomer, intramolecular hydrogen bond with the -OCF3 group is additionally formed, weaker, however, than that in the analogous -OCH3 derivative, which has been determined by both X-Ray measurements as well as theoretical DFT calculations. Docking studies showed possible interactions of the investigated compounds with LeuRS of Escherichia coli. Finally, the antibacterial potency of studied boronic acids in vitro were evaluated against Escherichia coli and Bacillus cereus.

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“…Benzoxaborole (2), 5-fluoro-substituted benzoxaborole (3) and 3-piperazine-bis(benzoxaborole) (4) were synthesized at the Faculty of Chemistry of Warsaw University of Technology by the research team of Prof. Agnieszka Adamczyk–Woźniak. Studies under aryl boronic acids stability showed that these compounds are stable under conditions of experiments (aquatic medium) [ 14 , 39 ].…”

Section: Methodsmentioning

confidence: 99%

Boronic Acids of Pharmaceutical Importance Affect the Growth and Photosynthetic Apparatus of Cyanobacteria in a Dose-Dependent Manner

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Pogrzeba

Adamczyk‐Woźniak

et al. 2020

Toxins

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The dynamic increase in the commercial application of antimicrobial derivatives of boronic acids, and potential impact of their presence in aquatic systems, supports the necessity to study the toxicity of these substances towards microorganisms of crucial meaning in the environment. One example of the mentioned derivatives is tavaborole (5-fluoro-substituted benzoxaborole), a pharmaceutical agent with antifungal activity. Cyanobacteria were used as model organisms, which are photoautotrophic prokaryotes, as representative aquatic bacteria and photoautotrophs associated with the plant kingdom. To the best of our knowledge, we investigated this issue for the first time. In order to recognize the under-stress response of those microorganisms, the concentration of photopigments—a key factor in the activity of photosynthetic apparatus—was measured spectrophotometrically. We found that the 3-piperazine bis(benzoxaborole) significantly suppressed the growth of halophilic and freshwater cyanobacteria, at a concentration 3.0 mM and 0.3 mM, respectively. Our results also showed that the tested substances at micromolar concentrations stimulated the growth of cyanobacteria, particularly in the freshwater strain Chroococcidiopsis thermalis. The tested substances acted with various strengths, depending on their structure and concentration; nevertheless, they had a greater influence on the synthesis of phycobiliproteins (e.g., lowered their concentration) than on the formation of chlorophyll and carotenoids.

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Fluorinated Boronic Acids: Acidity and Hydrolytic Stability of Fluorinated Phenylboronic Acids

Cited by 30 publications

References 32 publications

Dehydration of ortho‐, meta‐ and para‐Alkoxy Phenylboronic Acids to their Corresponding Boroxines

Dehydration of ortho‐, meta‐ and para‐Alkoxy Phenylboronic Acids to their Corresponding Boroxines

(Trifluoromethoxy)Phenylboronic Acids: Structures, Properties, and Antibacterial Activity

Boronic Acids of Pharmaceutical Importance Affect the Growth and Photosynthetic Apparatus of Cyanobacteria in a Dose-Dependent Manner

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