. Can. J. Chem. 53, 986 (1975). Under conditions of slow intermolecular hydroxyl proton exchange 6Jp0H.F < 0, SJtr.nsOH.F > 0, SJcI,OH~F < 0, 4J00H*F < 0 in fluorophenol derivatives. 'J,OHsF is remarkably insensitive to intrinsic substituent effects, yields accurate values of conformational populations of m-fluorophenol derivatives and can be used to demonstrate a buttressing effect on the strength of the relatively weak 0-H-halogen hydrogen bond. 4J,0H.F displays a stereospecific dependence opposite to that of other couplings from a side-chain proton to a ring fluorine nucleus, is apparently very sensitive to the distance between proton and fluorine nucleus and is cited as an example of a negative through-space coupling ,mechanism. Approximate molecular orbital calculations give some support to the last suggestion. [Traduit par le journal]

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