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19F and 13C GIAO-NMR chemical shifts for the identification of perfluoro-quinoline and -isoquinoline derivatives

Fox, M.A.; Pattison, G.; Sandford, G.; Batsanov, A.S.

19F and 13C GIAO-NMR chemical shifts for the identification of perfluoro-quinoline and -isoquinoline derivatives Thumbnail


Authors

G. Pattison

G. Sandford

A.S. Batsanov



Abstract

Reaction of perfluoroquinoline 1 and perfluoroisoquinoline 2 with benzylamine gave mono- and di-aminated quinoline and isoquinoline systems, respectively, depending upon the reaction conditions by selective SNAr processes. Optimised model geometries of the aminated derivatives at MP2/6-31G* were in very good agreement with available X-ray crystallographic data and were used to compute 19F and 13C GIAO-NMR shifts. Comparison with observed 19F and 13C NMR shifts give excellent correlations, indicating that 19F and 13C GIAO-NMR computations are powerful tools in structurally identifying polyfunctional, polycyclic perfluoroheteroaromatic compounds and aiding NMR resonance assignment.

Citation

Fox, M., Pattison, G., Sandford, G., & Batsanov, A. (2013). 19F and 13C GIAO-NMR chemical shifts for the identification of perfluoro-quinoline and -isoquinoline derivatives. Journal of Fluorine Chemistry, 155, 62-71. https://doi.org/10.1016/j.jfluchem.2013.05.005

Journal Article Type Article
Publication Date Nov 1, 2013
Deposit Date May 16, 2014
Publicly Available Date Mar 29, 2024
Journal Journal of Fluorine Chemistry
Print ISSN 0022-1139
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 155
Pages 62-71
DOI https://doi.org/10.1016/j.jfluchem.2013.05.005
Keywords Perfluoroheteroaromatic, Nucleophilic aromatic substitution, Perfluoroquinoline, NMR spectroscopy.

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Copyright Statement
NOTICE: this is the author’s version of a work that was accepted for publication in Journal of fluorine chemistry. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of fluorine chemistry, 165, 2013, 10.1016/j.jfluchem.2013.05.005




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