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.

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: May 21, 2014
• Journal: Journal of Fluorine Chemistry
• Print ISSN: 0022-1139
• Electronic ISSN: 1873-3328
• 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.
• Public URL: https://durham-repository.worktribe.com/output/1432051