Hydrogen bonds in phenylboronic acids with polyoxaalkyl substituents at ortho-position

Adamczyk‐Woźniak, Agnieszka; Cyrański, Michał K.; Dąbrowska, Aldona; Gierczyk, Błażej; Klimentowska, Paulina; Schroeder, Grzegorz; Żubrowska, Anna; Sporzyński, Andrzej

doi:10.1016/j.molstruc.2008.12.006

Cited by 21 publications

(14 citation statements)

References 15 publications

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“…The paper presents a comprehensive NMR spectroscopic characterization ( 1 H, 11 B, 13 C, 19 F, and 17 O) of all fluoro‐substituted phenylboronic acids (Fig. ) and is a continuation of our previous NMR studies on boronic acids and its derivatives …”

Section: Introductionmentioning

confidence: 93%

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Gierczyk

Kaźmierczak

Popenda

et al. 2014

Magnetic Reson in Chemistry

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The paper presents results of a systematic NMR studies on fluorinated phenylboronic acids. All possible derivatives were studied. The experimental (1)H, (13)C, (19)F, (11)B, and (17)O spectral data were compared with the results of theoretical calculations. The relation between the calculated natural bond orbital parameters and spectral data (chemical shifts and coupling constants) is discussed. The first examples of (10)B/(11)B isotopic effect on the (19)F spectra and (4)JFO scalar coupling in organic compounds are reported.

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Section: Introductionmentioning

confidence: 93%

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Gierczyk

Kaźmierczak

Popenda

et al. 2014

Magnetic Reson in Chemistry

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“…Such a twist is characteristic for a number of arylboronic acids as it allows one to avoid sterical repulsion between aromatic moieties from molecules arranged in side hydrogen-bond interactions [ 5 ]. In turn, the conformation of molecule 1 carrying the OCF 3 substituent in the ortho position is predefined by the O2–H2A…O3 intramolecular hydrogen bond ( d O…O = 2.839(2) Å; d H…O = 2.38(2) Å) [ 34 ]. Thus τ C2C1B1O1 dihedral angle is higher and equals to 26.5(1)°.…”

Section: Resultsmentioning

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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“…In particular, the influence of the substituents present in the phenyl ring of phenylboronic acids and their derivatives on the 17 O chemical shift have been investigated. 151,152 The largest changes of 17 O shifts were observed for the ortho position. The effect of intermolecular hydrogen bond formation in the boronic acids also has been detected by 17 O chemical shift changes.…”

Section: Applications Of 17 O Nmr In Chemistry and Materialsmentioning

confidence: 94%

17o NMR

Castiglione

Raos

2015

Annual Reports on NMR Spectroscopy

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This review summarizes recent developments in the area of liquid-state Nuclear Magnetic Resonance spectroscopy of the 17 O nucleus. It is structured in Sections, respectively covering (a) general background information, with special emphasis on spin relaxation phenomena for quadrupolar nuclei and in paramagnetic environments, (b) methods for the calculation of 17 O NMR parameters, with illustrative results, (c) applications in chemistry and materials science, (d) application to biomolecules and biological systems, (e) relaxation phenomena, including contrast agents for Magnetic Resonance Imaging (MRI). The 17 O nucleus emerges as a very sensitive probe of the local environment ─ including both bonding and non-bonding interactions ─ and molecular motions.

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Hydrogen bonds in phenylboronic acids with polyoxaalkyl substituents at ortho-position

Cited by 21 publications

References 15 publications

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Influence of fluorine substituents on the NMR properties of phenylboronic acids

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

17o NMR

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