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Durham University

Department of Chemistry

Publication details for Prof. Graham Sandford

Fox, M.A., Pattison, G., Sandford, G. & 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: 62-71.

Author(s) from Durham


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.