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Substituent‐Induced 1 H Chemical Shifts of 3‐Substituted Camphors
Author(s) -
Kaiser Carlos R.,
Rittner Roberto,
Basso Ernani A.
Publication year - 1997
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199709)35:9<609::aid-omr133>3.0.co;2-t
Subject(s) - substituent , chemistry , steric effects , chemical shift , proton , electronic effect , proton nmr , computational chemistry , stereochemistry , physics , quantum mechanics
The high‐field 1 H NMR analysis of 3‐substituted camphors with OH, OMe, SMe, NHMe, NMe 2 and Me substituents at endo and exo positions, and also with an oxo substituent, is reported. The substituent‐induced chemical shifts (SCS) obtained for these difunctional systems, including those from previous work on 3‐halocamphors, were examined in view of multilinear correlations with steric and electronic parameters. The resultant data show a strong contribution from the electric field mechanism, principally for the protons closer to the substituent. Carbonyl group interference on the expected SCS for the α‐proton is also observed, with less deshielding than those of substituted bornanes and norbornanes. © 1997 by John Wiley & Sons, Ltd.