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

doi:10.1016/j.jfluchem.2013.05.005

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 journal › Article › peer-review

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 language	English
Pages (from-to)	62-71
Number of pages	10
Journal	Journal of Fluorine Chemistry
Volume	155
DOIs	https://doi.org/10.1016/j.jfluchem.2013.05.005
Publication status	Published - 12 Jun 2013

Keywords

NMR spectroscopy
Nucleophilic aromatic substitution
Perfluoroheteroaromatic
Perfluoroquinoline

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10.1016/j.jfluchem.2013.05.005

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

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.",

keywords = "NMR spectroscopy, Nucleophilic aromatic substitution, Perfluoroheteroaromatic, Perfluoroquinoline",

author = "Fox, \{Mark A.\} and Graham Pattison and Graham Sandford and Batsanov, \{Andrei S.\}",

year = "2013",

month = jun,

day = "12",

doi = "10.1016/j.jfluchem.2013.05.005",

language = "English",

volume = "155",

pages = "62--71",

journal = "Journal of Fluorine Chemistry",

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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

N2 - 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.

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

KW - Perfluoroquinoline

UR - https://www.scopus.com/pages/publications/84884501610

U2 - 10.1016/j.jfluchem.2013.05.005

DO - 10.1016/j.jfluchem.2013.05.005

M3 - Article

AN - SCOPUS:84884501610

SN - 0022-1139

VL - 155

SP - 62

EP - 71

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

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

Abstract

Keywords

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