New 19F NMR methodology reveals structures of molecules in complex mixtures of fluorinated compounds

Although the number of natural fluorinated compounds is very small, fluorinated pharmaceuticals and agrochemicals are numerous. 19F NMR spectroscopy has a great potential for the structure elucidation of fluorinated organic molecules, starting with their production by chemical or chemoenzymatic reac...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2022-03, Vol.13 (13), p.3766-3774
Main Authors: Smith, Alan J R, York, Richard, Uhrín, Dušan, Bell, Nicholle G A
Format: Article
Language:English
Subjects:
Agrochemicals
Biological activity
Chemical reactions
Chemistry
Fluorination
Mixtures
Molecular structure
NMR spectroscopy
Organic chemistry
Parameter sensitivity
Phenols
Reaction mechanisms
Structural integrity
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Summary:Although the number of natural fluorinated compounds is very small, fluorinated pharmaceuticals and agrochemicals are numerous. 19F NMR spectroscopy has a great potential for the structure elucidation of fluorinated organic molecules, starting with their production by chemical or chemoenzymatic reactions, through monitoring their structural integrity, to their biotic and abiotic transformation and ultimate degradation in the environment. Additionally, choosing to incorporate 19F into any organic molecule opens a convenient route to study reaction mechanisms and kinetics. Addressing limitations of the existing 19F NMR techniques, we have developed methodology that uses 19F as a powerful spectroscopic spy to study mixtures of fluorinated molecules. The proposed 19F-centred NMR analysis utilises the substantial resolution and sensitivity of 19F to obtain a large number of NMR parameters, which enable structure determination of fluorinated compounds without the need for their separation or the use of standards. Here we illustrate the 19F-centred structure determination process and demonstrate its power by successfully elucidating the structures of chloramination disinfectant by-products of a single mono-fluorinated phenolic compound, which would have been impossible otherwise. This novel NMR approach for the structure elucidation of molecules in complex mixtures represents a major contribution towards the analysis of chemical and biological processes involving fluorinated compounds.
ISSN:2041-6520
2041-6539
DOI:10.1039/d1sc06057k