3-Alkoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium salts-based chiral ionic liquids

A new group of imidazolium salt-based chiral ionic liquids have been prepared and characterized. The chiral ionic liquids obtained are stable in air, in contact with water and popular organic solvents. Their physicochemical properties, single-crystal X-ray structures, antimicrobial activities, and antielectrostatic effects have been determined. The chiral ionic liquids synthesized have proven to represent not only potential new solvents in asymmetric synthesis but also effective disinfectants with antielectrostatic activity.

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3-Ethoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium chlorideC17H31ClN2O2[α]D20=-137.6 (c 0.45, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-propoxymethylimidazolium chlorideC18H33ClN2O2[α]D20=-86.1 (c 0.9, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

3-Butoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium chlorideC19H35ClN2O2[α]D20=-59.7 (c 1.0, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-pentyloxymethylimidazolium chlorideC20H37ClN2O2[α]D20=-76.0 (c 1.7, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

3-Hexyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium chlorideC21H39ClN2O2[α]D20=-71.6 (c 0.8, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

3-Heptyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium chlorideC22H41ClN2O2[α]D20=-72.0 (c 0.7, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-octyloxymethylimidazolium chlorideC23H43ClN2O2[α]D20=-67.6 (c 1.4, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-nonyloxymethylimidazolium chlorideC24H45ClN2O2[α]D20=-60.65 (c 0.9, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

3-Decyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium chlorideC25H47ClN2O2[α]D20=-59.9 (c 1.5, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-undecyloxymethylimidazolium chlorideC26H49ClN2O2[α]D20=-61.5 (c 1.2, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

3-Dodecyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium chlorideC27H51ClN2O2[α]D20=-65.2 (c 0.95, EtOH)Chiral alkoxymethylimidazolium chlorideAbsolute configuration: (1R,2S,5R)

3-Ethoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium tetrafluoroborateC17H31BF4N2O2[α]D20=-83.7 (c 0.6, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-propoxymethylimidazolium tetrafluoroborateC18H33BF4N2O2[α]D20=-98.3 (c 0.9, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Butoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium tetrafluoroborateC19H35BF4N2O2[α]D20=-104.9 (c 0.6, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-pentyloxymethylimidazolium tetrafluoroborateC20H37BF4N2O2[α]D20=-75.2 (c 0.7, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Hexyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium tetrafluoroborateC21H39BF4N2O2[α]D20=-78.6 (c 0.6, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Heptyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium tetrafluoroborateC22H41BF4N2O2[α]D20=-66.2 (c 1.5, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-octyloxymethylimidazolium tetrafluoroborateC23H43BF4N2O2[α]D20=-62.1 (c 1.6, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-nonyloxymethylimidazolium tetrafluoroborateC24H45BF4N2O2[α]D20=-67.6 (c 1.4, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Decyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium tetrafluoroborateC25H47BF4N2O2[α]D20=-55.4 (c 1.1, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-undecyloxymethylimidazolium tetrafluoroborateC26H49BF4N2O2[α]D20=-54.3 (c 1.9, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Dodecyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium tetrafluoroborateC27H51BF4N2O2[α]D20=-52.6 (c 1.4, EtOH)Chiral alkoxymethylimidazolium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Ethoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium perchlorateC17H31ClN2O2[α]D20=-80.8 (c 0.6, EtOH)Chiral alkoxymethylimidazolium perchlorateAbsolute configuration: (1R,2S,5R)

3-Ethoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium hexafluorophosphateC17H31F6N2O2P[α]D20=-75.1 (c 0.5, EtOH)Chiral alkoxymethylimidazolium hexafluorophosphateAbsolute configuration: (1R,2S,5R)

3-Ethoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium bis(trifluoromethanesulfonyl)imideC19H31F6N3O6S2[α]D20=-55.2 (c 1.1, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-propoxymethylimidazolium bis(trifluoromethanesulfonyl)imideC20H33F6N3O6S2[α]D20=-54.1 (c 0.7, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

3-Butoxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium bis(trifluoromethanesulfonyl)imideC21H35F6N3O6S2[α]D20=-51.2 (c 0.95, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-pentyloxymethylimidazolium bis(trifluoromethanesulfonyl)imideC22H37F6N3O6S2[α]D20=-49.3 (c 1.1, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

3-Hexyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium bis(trifluoromethanesulfonyl)imideC23H39F6N3O6S2[α]D20=-47.6 (c 0.9, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

3-Heptyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium bis(trifluoromethanesulfonyl)imideC24H41F6N3O6S2[α]D20=-45.7 (c 1.1, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-octyloxymethylimidazolium bis(trifluoromethanesulfonyl)imideC25H43F6N3O6S2[α]D20=-44.4 (c 1.2, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-nonyloxymethylimidazolium bis(trifluoromethanesulfonyl)imideC26H45F6N3O6S2[α]D20=-41.3 (c 1.4, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

3-Decyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium bis(trifluoromethanesulfonyl)imideC27H47F6N3O6S2[α]D20=-40.7 (c 2.2, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

1-(1R,2S,5R)-(−)-Menthoxymethyl-3-undecyloxymethylimidazolium bis(trifluoromethanesulfonyl)imideC28H49F6N3O6S2[α]D20=-34.4 (c 1.1, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)

3-Dodecyloxymethyl-1-(1R,2S,5R)-(−)-menthoxymethylimidazolium bis(trifluoromethanesulfonyl)imideC29H51F6N3O6S2[α]D20=-32.1 (c 1.0, EtOH)Chiral alkoxymethylimidazolium bis(trifluoromethanesulfonyl)imideAbsolute configuration: (1R,2S,5R)