||Substituent Effects and Additivity in the Carbon-13 Nuclear Magnetic Resonance Spectra of Chlorinated Naphthalenes and Their Chlorinated Naphthol Metabolites.
Wilson, Nancy K. ;
Zehr, Robert D. ;
||Health Effects Research Lab., Research Triangle Park, NC. Environmental Toxicology Div.
Nuclear magnetic resonance ;
Chlorine organic compounds ;
Carbon isotopes ;
Proton magnetic resonance ;
Chlorinated naphthalenes ;
Carbon 13 ;
Chemical shifts(Nuclear magnetic resonance) ;
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Carbon-13 and proton nuclear magnetic resonance spectra were obtained for 12 chlorinated naphthalenes and six chlorinated naphthols, some of which are metabolites of the naphthalenes. The validity of the use of additivity of chlorine and hydroxyl substituent effects to predict 13-C chemical shifts in these compounds was examined. Deviations from the additivity predictions resulted from per and ortho substituent interactions, both steric and hydrogen bonding. Despite these deviations, additive substituent parameters could be used to assign 13-C spectra correctly and to distinguish uniquely between similar isomers. (Portions of this document are not fully legible)