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Visualization and quantification of anisotropic effects on the 1H NMR spectra of 1,3-oxazino[4,3- alpha]isoquinolines - indirect estimates of steric compression

  • The anisotropic effects of the phenyl, alpha- and beta-naphthyl moieties in four series of 1,3-oxazino[4,3- a]isoquinolines on the H-1 chemical shifts of the isoquinoline protons were calculated by employing the Nucleus Independent Chemical Shift (NICS) concept and Visualized as anisotropic cones by a through-space NMR shielding grid. The signs and extents of these spatial effects on the H-1 chemical shifts of the isoquinoline protons were compared with the experimental H-1 NMR spectra. The differences between the experimental delta (H-1)/ppm values and the calculated anisotropic effects of the aromatic moieties are discussed in terms of the steric compression that occurs in the Compounds studied.

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Author details:Erich KleinpeterORCiDGND, István SzatmáriORCiD, László Lázár, Andreas KochORCiDGND, Matthias HeydenreichORCiD, Ferenc FulopORCiD
DOI:https://doi.org/10.1016/j.tet.2009.07.038
ISSN:0040-4020
Publication type:Article
Language:English
Year of first publication:2009
Publication year:2009
Release date:2017/03/25
Source:Tetrahedron. - ISSN 0040-4020. - 65 (2009), 38, S. 8021 - 8027
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer review:Referiert
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