Abstract
The conformational analyses of α-mono, α-di and α-trichloroacetanilides have been carried out using IR spectroscopy. α-Monochloro, dichloro and trichloroacetanilides were found to exist in only one conformation in CH2Cl2 and CHC13. The existence of all these anilides in single conformation is due to intramolecular H-bond formation between N−H and Cl.
In CH3CN, the broadening of C–0 bands of monochloroacetanilides and their bifurcation in α-dichloroacetanilides indicated the existence of two rotamers due to the breaking of chelation by the solvent.
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Venkateshwarlu, G., Reddy, P.P. & Subrahmanyam, B. Conformations ofαchloroacetanilides: An IR spectroscopic study. Proc. Indian Acad. Sci. (Chem. Sci.) 101, 75–82 (1989). https://doi.org/10.1007/BF02869388
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DOI: https://doi.org/10.1007/BF02869388