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

Reaction of perfluoroquinoline 1 and perfluoroisoquinoline 2 with benzylamine gave mono- and diaminated 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 F-19 and C-13 GIAO-NMR shifts. Comparison with observed F-19 and C-13 NMR shifts give excellent correlations, indicating that F-19 and C-13 GIAO-NMR computations are powerful tools in structurally identifying polyfunctional, polycyclic perfluoroheteroaromatic compounds and aiding NMR resonance assignment. (C) 2013 Elsevier B.V. All rights reserved.