Konformationsuntersuchungen mit Hilfe der 13C‐NMR‐Spektroskopie. IV. Additive Berechnung der 13C‐chemischen Verschiebungen in 2‐Brom‐cycloalkanolen und 2‐Brom‐1‐methoxy‐cycloalkanen unterschiedlicher Ringgröße
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Media type:
E-Article
Title:
Konformationsuntersuchungen mit Hilfe der 13C‐NMR‐Spektroskopie. IV. Additive Berechnung der 13C‐chemischen Verschiebungen in 2‐Brom‐cycloalkanolen und 2‐Brom‐1‐methoxy‐cycloalkanen unterschiedlicher Ringgröße
Contributor:
Kleinpeter, E.;
Haufe, G.;
Borsdorf, R.
imprint:
Wiley, 1980
Published in:Journal für Praktische Chemie
Language:
English
DOI:
10.1002/prac.19803220115
ISSN:
0021-8383
Origination:
Footnote:
Description:
<jats:p><jats:bold>Conformational Investigations by Means of <jats:sup>13</jats:sup>C‐N.M.R.Spectroscopy. IV. Additive Calculation of the <jats:sup>13</jats:sup>C‐N.M.R. Chemical Shifts in 2‐Bromo‐cycloalkanoles and 2‐Bromo‐1‐methoxy‐cycloalkanes of Different Ring Size</jats:bold></jats:p><jats:p>The <jats:sup>13</jats:sup>C‐n.m.r. spectra of a series of bromo‐cycloalkanes, cycloalkanoles, methoxy‐cycloalkanes, trans‐2‐bromo‐cycloalkanoles and trans‐2‐bromo‐1‐methoxy‐cycloalkanes (ring size n = 5, 6, 7, 8, 12) as well as cis‐2‐bromo‐cyclododecanol and cis‐2‐bromo‐1‐methoxycyclododecane are obtained and assigned. The <jats:sup>13</jats:sup>C‐chemical shifts of the monosubstituted compounds have been used to estimate the substituent effects of bromo, hydroxy and methoxy groups to the α‐, β‐ and γ‐position. Using these shift parameters, the <jats:sup>13</jats:sup>C‐chemical shifts of the vicinal disubstituted compounds are calculated in an additive incremental manner. These <jats:sup>13</jats:sup>C‐chemical shifts have been compared with the experimental values and the differences are discussed with respect to the magnitude of the deviations from additivity with the dimension of steric and electronic interaction of the vicinal substituents.</jats:p>