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Structural examination of some polychlorinated 2‐phenoxyphenols by 1 H and 13 C nuclear magnetic resonance
Author(s) -
Nordén Bo,
Edlund Ulf,
Nilsson CarlAxel
Publication year - 1980
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270130602
Subject(s) - steric effects , intramolecular force , chemistry , chemical shift , moiety , substituent , chlorine , nmr spectra database , aryl , ring (chemistry) , ether , chlorine atom , intermolecular force , nuclear magnetic resonance spectroscopy , crystallography , molecule , spectral line , stereochemistry , medicinal chemistry , organic chemistry , physics , alkyl , astronomy
Carbon‐13 NMR spectra of some polychlorinated 2‐phenoxyphenols have been obtained. The substituent chemical shifts obtained by varying the chlorine substitution pattern of one ring are very similar to those reported for the corresponding diphenyl ethers. Thus, the replacement of a 2‐chlorine atom by a hydroxyl group only induces minor shielding changes at the adjacent aryl moiety and the 13 C chemical shift changes are mainly determined by the preferred conformations governed by the steric demand of the ortho substituents. An 1 H NMR/IR study revealed an equilibrium between intermolecular aggregates and intramolecular OH…π species in the concentration interval 2‐0.005 M. Any hydrogen bonding effects on 13 C NMR shieldings are, therefore, minor compared to shielding variations caused by steric perturbations.