Signs of proton–proton and proton–fluorine spin–spin coupling constants in 2-fluoro-3-methylpyridine. Sigma and pi contributions to coupling in a nitrogen heterocycle

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Abstract
The signs of all proton–proton and proton–fluorine spin–spin coupling constants in 2-fluoro-3-methylpyridine have been determined by double and triple resonance experiments. The signs of the longrange coupling constants, JH,CH3 and JF,CH3 are the same as in fluorotoluene derivatives. Their magnitudes are consistent with the assumption that the nitrogen atom primarily polarizes the σ bonds in the molecule, leaving the π contribution to the long-range coupling relatively unaffected.

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