Solubility of phenylboronic compounds in water

Sporzyński, Andrzej; Leszczyński, Paweł

doi:10.13171/mjc65/01711030630-sporzynski

Cited by 5 publications

(3 citation statements)

References 6 publications

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“…One can also find some generalized and misleading statements in the literature such as "boronic acids are water soluble" [10] or "since the reactants are insoluble in water, this reaction is an > on water < reaction" [11]. Only recently, solubilities of several simple arylboronic acid and benzoxaboroles in water were published [12]. It was found, that solubility of this class of compounds was low, with the value of 1.9 g/100 g H 2 O for phenylboronic acid at 20 ºC and even lower for some substituted compounds.…”

Section: Introductionmentioning

confidence: 99%

Solubility of Phenylboronic Acid and its Cyclic Esters in Organic Solvents

2020

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The solubilities of phenylboronic acid, its pinacol ester and azaester in organic solvents (chloroform, 3-pentanone, acetone, dipropyl ether and methylcyclohexane) have been determined experimentally by a dynamic method, in which the disappearance of turbidity was determined by measuring of light intensity using a luminance probe. Phenylboronic acid has high solubility in ether and ketones, moderate in chloroform and very low in hydrocarbon. Pinacol ester and azaester show better solubility than the parent acid in all tested solvents. For pinacol ester differences between particular solvents are small, while for azaester the differences are significant. For both esters the highest solubility is observed in chloroform and the lowest in the hydrocarbon. The results have been correlated by the Wilson, NRTL and Redlich-Kister equations. For the phenylboronic acid better correlation of the data is obtained by polynomials in comparison with the above equations. It is connected with additional acid-anhydride equilibrium in the system. The influence of polarity of the solvents on the solubility is discussed.

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Section: Introductionmentioning

confidence: 99%

Solubility of Phenylboronic Acid and its Cyclic Esters in Organic Solvents

2020

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“…In the DSC data, we observed a clear thermal event for the PhBA at ∼80 °C attributing to a dehydration event. 52,53 In the case of the OTHO1-PhBA xerogel, we observed a similar thermal event at a much higher temperature indicating that the boronic ester formed during gel formation is more thermally stable than the parent boronic acid.…”

Section: ■ Results and Discussionmentioning

confidence: 57%

“…For the OTHO1-BA xerogel, we did not observe any significant changes in the onset degradation temperature compared to BA indicating that the hybrid system is not contributing to the thermal stability. In the DSC data, we observed a clear thermal event for the PhBA at ∼80 °C attributing to a dehydration event. , In the case of the OTHO1-PhBA xerogel, we observed a similar thermal event at a much higher temperature indicating that the boronic ester formed during gel formation is more thermally stable than the parent boronic acid.…”

Section: Resultsmentioning

confidence: 61%

Dual Role of Boronic Acid Modification in Enhancing Rheological and Photophysical Properties of Supramolecular Gels

Saha,

Ruiu,

Zacharias

et al. 2024

Macromolecules

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Supramolecular gels derived from functionalized gelators offer diverse applications, and modifying the properties of existing organogels using guest molecules presents an attractive approach for designing functional gel materials with targeted properties. In this study, we investigated a method to enhance the mechanical and photophysical properties of readily prepared low molecular weight gels (LMWGs) through the incorporation of boronic acid derivatives. The leveraging of dynamic covalent bonding interactions between the hydroxyl groups of oxotriphenylhexanoates (OTHO) gelator and the boronic acid derivatives gave rise to a boronate adduct along with enhanced intermolecular aromatic stacking interactions between gelators and thereby reinforced the rheological and thermal stability of the doped OTHO gels. In an effort to probe the aforementioned aromatic interactions, we used a pyrene boronic acid dopant, which revealed that the spatial proximity between the aromatic groups of the boronic acid was close enough to display excimer formation. Our findings provide valuable insights into the regulation of mechanical strength, self-healing ability, and photophysical properties of supramolecular gels. Furthermore, this approach holds promise for broad applications in hydroxyl-containing LMWGs, enabling the development of functional gel materials with enhanced properties.

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