Measurement of H/D isotope effects on the (19)F resonances of sequentially deuterated 1-n-butyl-3-methylimidazolium hexafluorophosphate and tetrafluoroborate isotopologues reveals the formation of aliphatic C-H···X hydrogen bonds between the fluorinated anions and protons along the N-alkyl sidechains of the cations.

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Deuterium isotopologues of the ionic liquid (IL) 1-n-butyl-3-methylimidazolium chloride ([C 4 mim]Cl) sequentially labeled on the C-1 00 , C-1 0 , C-2 0 , C-3 0 , and C-4 0 positions of the N-alkyl groups were prepared following a strategy that minimizes the number of distinct reactions through the use of analogous synthetic routes. In several cases, good yields after the initial deuterium incorporation reaction were achieved by combining well-established chemical transformations into efficient single-step processes.