Chiral pyridinium-based ionic liquids containing the (1R,2S,5R)-(−)-menthyl group

A novel class of chiral pyridinium salts in which the chirality resides in the cation have been prepared and characterized. The physicochemical and anti-microbial properties have been determined. The group of prepared salts contained chiral ionic liquids and decomposable chiral pyridinium chlorides.

A novel class of chiral pyridinium salts in which the chirality resided in the cation have been prepared and characterized. The physicochemical and anti-microbial properties have been determined. The group of prepared salts contained chiral ionic liquids and decomposable chiral pyridinium chlorides.Figure optionsDownload as PowerPoint slide

1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium chlorideC16H26ClNO[α]D20=-124.2 (c 0.9, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-2-methylpyridinium chlorideC17H28ClNO[α]D20=-99.7 (c 0.5, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-3-methylpyridinium chlorideC17H28ClNO[α]D20=-126.9 (c 0.6, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-4-methylpyridinium chlorideC17H28ClNO[α]D20=-117.1 (c 1.3, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

4-Ethyl-1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium chlorideC18H30ClNO[α]D20=-124.8 (c 1.0, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

4-tert-Butyl-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium chlorideC20H34ClNO[α]D20=-102.7 (c 1.3, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

5-Hydroxy-1-[(1R,2S,5R)-(−)-menthoxymethyl]-2-methylpyridinium chlorideC17H28ClNO2[α]D20=-120.9 (c 1.1, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

3-Carbamoyl-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium chlorideC17H27ClN2O2[α]D20=-122.2 (c 1.0, EtOH)Decomposable chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

3-Hydroxy-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium chlorideC16H26ClNO2[α]D20=-147.3 (c 1.0, EtOH)Decomposable chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-4-(dimethylamino)pyridinium chlorideC18H31ClN2O[α]D20=-117.8 (c 0.5, EtOH)Chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-3-(dimethylamino)pyridinium chlorideC18H31ClN2O[α]D20=-154.6 (c 1.0, EtOH)Decomposable chiral pyridinium chlorideAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium tetrafluoroborateC16H26BF4NO[α]D20=-116.5 (c 0.7, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-2-methylpyridinium tetrafluoroborateC17H28BF4NO[α]D20=-116.3 (c 1.0, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-3-methylpyridinium tetrafluoroborateC17H28BF4NO[α]D20=-116.9 (c 1.0, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-4-methylpyridinium tetrafluoroborateC17H28BF4NO[α]D20=-109.9 (c 0.7, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

4-Ethyl-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium tetrafluoroborateC18H30BF4NO[α]D20=-112.2 (c 1.1, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

5-Hydroxy-1-[(1R,2S,5R)-(−)-menthoxymethyl]-2-methylpyridinium tetrafluoroborateC17H28BF4NO2[α]D20=-108.9 (c 1.0, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Carbamoyl-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium tetrafluoroborateC17H27BF4N2O2[α]D20=-111.9 (c 1.0, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

3-Hydroxy-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium tetrafluoroborateC16H26BF4NO2[α]D20=-114.8 (c 1.0, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-4-(dimethylamino)pyridinium tetrafluoroborateC18H31BF4N2O[α]D20=-112.6 (c 1.0, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-3-(dimethylamino)pyridinium tetrafluoroborateC18H31BF4N2O[α]D20=-139.4 (c 0.5, EtOH)Chiral pyridinium tetrafluoroborateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium perchlorateC16H26ClNO5[α]D20=-110.9 (c 0.6, EtOH)Chiral pyridinium perchlorateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium iodideC16H26INO[α]D20=-50.9 (c 0.8, EtOH)Chiral pyridinium iodideAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium hexafluorophosphateC16H26F6NOP[α]D20=-97.6 (c 1.0, EtOH)Chiral pyridinium hexafluorophosphateAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium bis(trifluoromethanesulfonyl)imideC18H26F6N2O5S2[α]D20=-70.9 (c 1.4, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-2-methylpyridinium bis(trifluoromethanesulfonyl)imideC19H28F6N2O5S2[α]D20=-77.2 (c 1.1, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-3-methylpyridinium bis(trifluoromethanesulfonyl)imideC19H28F6N2O5S2[α]D20=-70.3 (c 1.3, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-4-methylpyridinium bis(trifluoromethanesulfonyl)imideC19H28F6N2O5S2[α]D20=-71.2 (c 1.0, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)

4-ethyl-1-[(1R,2S,5R)-(−)-Menthoxymethyl]pyridinium bis(trifluoromethanesulfonyl)imideC20H30F6N2O5S2[α]D20=-69.7 (c 0.5, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)

4-tert-Butyl-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium bis(trifluoromethanesulfonyl)imideC22H34F6N2O5S2[α]D20=-70.4 (c 1.6, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)

3-Carbamoyl-1-[(1R,2S,5R)-(−)-menthoxymethyl]pyridinium bis(trifluoromethanesulfonyl)imideC19H27F6N3O6S2[α]D20=-75.4 (c 1.2, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)

1-[(1R,2S,5R)-(−)-Menthoxymethyl]-3-(dimethylamino)pyridinium bis(trifluoromethanesulfonyl)imideC20H31F6N3O5S2[α]D20=-92.5 (c 0.85, EtOH)Chiral ionic liquidAbsolute configuration: (1R,2S,5R)