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

Mark A. Fox, Graham Pattison, Graham Sandford, Andrei S. Batsanov

Research output: Contribution to journalArticle

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 S NAr 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.

Original languageEnglish
Pages (from-to)62-71
Number of pages10
JournalJournal of Fluorine Chemistry
Volume155
DOIs
Publication statusPublished - 12 Jun 2013

Fingerprint

quinoline
Chemical shift
chemical equilibrium
nuclear magnetic resonance
Nuclear magnetic resonance
Derivatives
Polycyclic Compounds
shift
X-Rays
geometry
X rays
Geometry
isoquinoline
chemical
Carbon-13 Magnetic Resonance Spectroscopy
x rays

Keywords

  • NMR spectroscopy
  • Nucleophilic aromatic substitution
  • Perfluoroheteroaromatic
  • Perfluoroquinoline

Cite this

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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 S NAr 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.",
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19F and 13C GIAO-NMR chemical shifts for the identification of perfluoro-quinoline and -isoquinoline derivatives. / Fox, Mark A.; Pattison, Graham; Sandford, Graham; Batsanov, Andrei S.

In: Journal of Fluorine Chemistry, Vol. 155, 12.06.2013, p. 62-71.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 19F and 13C GIAO-NMR chemical shifts for the identification of perfluoro-quinoline and -isoquinoline derivatives

AU - Fox, Mark A.

AU - Pattison, Graham

AU - Sandford, Graham

AU - Batsanov, Andrei S.

PY - 2013/6/12

Y1 - 2013/6/12

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AB - 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 S NAr 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.

KW - NMR spectroscopy

KW - Nucleophilic aromatic substitution

KW - Perfluoroheteroaromatic

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