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

Fox, M.A. and Pattison, G. and Sandford, G. and Batsanov, A.S. (2013) '19F and 13C GIAO-NMR chemical shifts for the identification of perfluoro-quinoline and -isoquinoline derivatives.', Journal of fluorine chemistry., 155 . pp. 62-71.


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.

Item Type:Article
Keywords:Perfluoroheteroaromatic, Nucleophilic aromatic substitution, Perfluoroquinoline, NMR spectroscopy.
Full text:(AM) Accepted Manuscript
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Publisher 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
Date accepted:No date available
Date deposited:21 May 2014
Date of first online publication:November 2013
Date first made open access:No date available

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