A study of the infrared spectra of primary, secondary and tertiary alkyl chlorides reveals that the frequency of the so-called C-Cl stretching mode is a function of the detailed structure in the vicinity of the C-Cl bond. In primary chlorides the frequency region depends on whether a hydrogen atom or a carbon atom is irons to the Cl atom across the common C-C bond. In secondary chlorides it is found that the trans substituents on both C-C bonds adjacent to the C-Cl bond are important in determining the frequency region, and a similar result is observed for the tertiary chlorides. Frequency ranges for the various rotationally isomeric structures of primary, secondary and tertiary chlorides are given.
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http://deepblue.lib.umich.edu/bitstream/2027.42/32341/1/0000411.pdf