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

Volume 19, Number 5 (Sept. 1965) Page 150-154

Sharpless, Norman E.; Bradley, Robert B.


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.