The n.m.r. spectra of four halogenoacetones (Me·CO·CH2X; X = F, Cl, Br, or I) protonated in super-acid media show strong long-range coupling through the sp2 centre and intramolecular hydrogen bonding, both directly related to the electronegativity of the heteroatom X.
R. Jost, P. Rimmelin and J. M. Sommer, J. Chem. Soc. D, 1971, 1243 DOI: 10.1039/C29710001243
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