Influence of fluorine substituents on the NMR properties of phenylboronic acids

Błażej Gierczyk; Marcin Kaźmierczak; Łukasz Popenda; Andrzej Sporzyński; Grzegorz Schroeder; Stefan Jurga

doi:10.1002/mrc.4051

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Magn Reson Chem. 2014 May;52(5):202-13. doi: 10.1002/mrc.4051. Epub 2014 Feb 11.

Authors

Błażej Gierczyk¹, Marcin Kaźmierczak, Łukasz Popenda, Andrzej Sporzyński, Grzegorz Schroeder, Stefan Jurga

Affiliation

¹ Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614, Poznań, Poland.

PMID: 24519471
DOI: 10.1002/mrc.4051

Abstract

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.

Keywords: DFT calculation; NMR; arylboronic acid; spectroscopy.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boronic Acids / chemistry*
Hydrocarbons, Fluorinated / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Quantum Theory
Reference Standards

Substances

Boronic Acids
Hydrocarbons, Fluorinated
benzeneboronic acid