The Nuclear Magnetic Resonance Spectra of Compounds Related to DDT. I. Non-Aromatic Protons

Authors: Sharpless, Norman E.; Bradley, Robert B.

Source: Applied Spectroscopy, Volume 19, Issue 5, Pages 141-166 (September 1965) , pp. 150-154(5)

Publisher: Society for Applied Spectroscopy

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Abstract:

The nuclear magnetic resonance spectra of a series of compounds related to DDT have been studied as they are influenced by ring or aliphatic substituents or by aliphatic structural changes

The chemical shift of the benzylic or α proton follows the Hammett equation for ring substituents and the Taft variation of this equation for aliphatic substituents. Alkoxy substituents on the ring show alternation of chemical shift of the –OCH2– group protons with chain length and limiting behavior of the terminal methyl group with chain length.

Dehydrochlorination of o,p-DDD produces cis-trans isomers.

Coupling constants are shown to be influenced by ring substitution, particularly ortho chlorine.

Document Type: Research Article

DOI: http://dx.doi.org/10.1366/000370265774415702

Affiliations: Laboratory of Physical Biology, National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, Bethesda, Maryland

Publication date: September 1, 1965

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