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The ion kinetic energy (IKE) and mass spectra of 1- and 2-chloronapthalenes and seven dichoronaphthalenes have been recorded and the spectra of each set of isomers are strikingly similar; comparison of the daughter ion peaks obtained from the IKE spectra indicate chlorine randomisation over at least one of the rings in the monosubstituted compounds and over both rings in the isomeric dichloronaphthalenes.
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Safe et al. (1972) studied this question.
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