0000000001309931
AUTHOR
Andrzej Sporzyński
5-Formyl-2-furanboronic acid at 100 K
The furan ring in the title compound, C5H5BO4, is planar and each of the formyl and boronic groups makes a dihedral angle of ca 3° with this ring. The geometry of the furan ring is somewhat different to that found for substituted and unsubstituted furan structures. The molecules are connected to each other in the bc plane by C—H⋯O and O—H⋯O hydrogen bonds.
The influence of fluorine position on the properties of fluorobenzoxaboroles
5-Fluoro-2,1-benzoxaborol-1(3H)-ol, a potent antifungal drug also known as Tavaborole or AN2690, has been compared with its three isomers in terms of its activity against several fungi as well as pKa and multinuclear NMR characterization. The molecular and crystal structure of 6-fluoro-2,1-benzoxaborol-1(3H)-ol was determined and compared with that of AN2690.
Novel 2,6-disubstituted phenylboronic compounds - Synthesis, crystal structures, solution behaviour and reactivity
Abstract 2,6-Diformylphenylboronic acid has been synthesized and characterized both in the solid state as well as in solution. In crystal, an unusual structural pattern has been found with the formation of intermolecular hydrogen bonds by B(OH) 2 and CHO groups as well as water molecules. In solution tautomeric equilibrium with the formation of oxaborole ring by one of the formyl groups was proved on the basis of multinuclear NMR spectroscopy. The title compound reacts with secondary mono- and diamines to form various types of substituted benzoxaboroles, which have been characterized by XRD and spectroscopic methods.
3-Formyl-2-furanboronic acid: X-ray and DFT studies
The molecule of the title compound, C5H5BO4, is almost planar with the boronic acid group inclined to the furan ring by 3.7 (1)°. DFT (density functional theory) calculations at the B3LYP/6-311+G** level of theory (with no imaginary frequencies) were used to approximate the influence of hydrogen bonding on the molecular geometry and have confirmed the planarity of the molecule. No significant differences in geometrical parameters in the solid state and in the gas phase are associated with the presence of the O—H⋯O intermolecular hydrogen-bonding network. The crystal packing is characterized by O—H⋯O hydrogen-bonded dimers, which are additionally linked by O—H⋯O, as well as C—H⋯O interactio…
(Trifluoromethoxy)Phenylboronic Acids: Structures, Properties, and Antibacterial Activity.
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 sol…
Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an electron-withdrawing substituent results in a considerable rise in the acidity in comparison with its analogues. In some solutions, the title compound isomerizes with formation of the corresponding 3-hydroxybenzoxaborole. Taking into account the probable mechanism of antifungal action of benzoxaboroles, which blocks the cytoplasmic leucyl-tRNA synthetase (LeuRS) of the microorganism, docking stud…
Investigation of fungicidal activity of 3-piperazine-bis(benzoxaborole) and its boronic acid analogue
3-Piperazine-bis(benzoxaborole) and its bis(phenylboronic acid) analogue were investigated in terms of their fungicidal activity. The study was carried out against five filamentous fungi: Aspergillus terreus, Fusarium dimerum, Fusarium solani, Penicillium ochrochloron and Aspergillus niger. 3-Piperazine-bis(benzoxaborole) revealed higher inhibitory activity towards the examined strains than standard antibiotic (amphotericin B), whereas bis(phenylboronic acid) proved to be inactive. The study unequivocally showed that the presence of the heterocyclic benzoxaborole system is essential for antifungal action of the examined compounds. Copyright © 2014 John Wiley & Sons, Ltd.
3-formylphenylboronic acid.
The molecule of the title compound, C(7)H(7)BO(3), is planar, and the bond lengths and angles are typical. The formyl group is essentially coplanar with the benzene ring but does not influence significantly the distortion of the ring, although the formyl group does have a strong influence on the crystal packing. The geometry of the boronic acid group is typical. In the crystal structure, the molecules are linked by O-H...O hydrogen bonds.
CCDC 1029677: Experimental Crystal Structure Determination
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CCDC 1959978: Experimental Crystal Structure Determination
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CCDC 1029678: Experimental Crystal Structure Determination
Related Article: Agnieszka Adamczyk-Woźniak, Krzysztof Ejsmont, Błażej Gierczyk, Ewa Kaczorowska, Alicja Matuszewska, Grzegorz Schroeder, Andrzej Sporzyński, Bartosz Zarychta|2015|J.Organomet.Chem.|788|36|doi:10.1016/j.jorganchem.2015.04.026
CCDC 1027467: Experimental Crystal Structure Determination
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