Supplement Information – Chromatographia

Gabriela Kučerová1, Květa Kalíková1,*, Hana Procházková1, Martin Popr2, Jindřich Jindřich2,

Pavel Coufal3, Eva Tesařová1

Chromatographic Characterization of a New Cationic β-CD Based Stationary Phase Prepared

by Dynamic Coating

1Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles

University in Prague, Hlavova 8, 128 43 Prague 2, Czech Republic

2Department of Organic Chemistry, Faculty of Science, Charles University in Prague,

Hlavova 8, 128 43 Prague 2, Czech Republic

3Department of Analytical Chemistry, Faculty of Science, Charles University in Prague,

Hlavova 8, 128 43 Prague 2, Czech Republic

*e-mail: kalikova@natur.cuni.cz, Tel.:+420221951299

Table S1. Set of tested analytes with their descriptors (for LFER study)

Analyte E S A B VToluene 0.601 0.520 0.000 0.140 0.8573Propylbenzene 0.604 0.500 0.000 0.150 1.1391Butylbenzene 0.600 0.510 0.000 0.150 1.2800Pentylbenzene 0.594 0.510 0.000 0.150 1.4209Naphthalene 1.340 0.920 0.000 0.200 1.0854Benzamide 0.990 1.500 0.490 0.670 0.9728Caffeine 1.500 1.720 0.000 1.280 1.3632Theophylline 1.500 1.600 0.540 1.340 1.2223Benzyl alcohol 0.803 0.870 0.390 0.560 0.9160Benzonitrile 0.742 1.110 0.000 0.330 0.8711Chlorobenzene 0.718 0.650 0.000 0.070 0.8388Bromobenzene 0.882 0.730 0.000 0.090 0.8914Benzophenone 1.447 1.500 0.000 0.500 1.4808Phenol 0.805 0.890 0.600 0.300 0.7751Pyrocatechol 0.970 1.100 0.880 0.470 0.8338Resorcinol 0.980 1.000 1.090 0.520 0.8338Hydroquinone 1.063 1.270 1.060 0.570 0.8337β-Naphthol 1.520 1.080 0.610 0.400 1.1440o-Xylene 0.663 0.560 0.000 0.160 0.9982m-Xylene 0.623 0.520 0.000 0.160 0.9982p-Xylene 0.613 0.520 0.000 0.160 0.9982o-Cresol 0.840 0.860 0.520 0.300 0.9160m-Cresol 0.822 0.880 0.570 0.340 0.91602,3-Dimethylphenol 0.850 0.850 0.520 0.360 1.05692,5-Dimethylphenol 0.840 0.790 0.540 0.370 1.05693,4-Dimethylphenol 0.830 0.860 0.560 0.390 1.0569o-Isopropylphenol 0.842 0.880 0.520 0.380 1.1978o-Chlorophenol 0.853 0.880 0.320 0.310 0.8975m-Chlorophenol 0.909 1.060 0.690 0.150 0.8975p-Chlorophenol 0.915 1.080 0.670 0.200 0.8975o-Nitrophenol 1.015 1.050 0.050 0.370 0.9493p-Nitrophenol 1.070 1.720 0.820 0.260 0.9493m-Nitrotoluene 0.874 1.100 0.000 0.250 1.0315Biphenyl 1.360 0.990 0.000 0.260 1.3242Anthracene 2.290 1.340 0.000 0.280 1.4544p-Cresol 0.820 0.870 0.570 0.310 0.9160

Table S2. Set of tested analytes with their pKA constants (for Ionic Interactions)

Analyte pKA [32,33]

Aniline 4.6

N-Ethylaniline 5.1

N,N-Diethylaniline 5.2

Benzenesulfonic acid -2.8

p-Toluenesulfonic acid -2.5

N,N,N-Trimethylanilinium chloride -9.8

PEMPDA-β-CD coated SP Commercial β-CD SPGroup/analyte k RS Group/analyte k RS

Group A Group ABenzene 1.23 Benzene 4.55Phenanthrene 1.72 2.40 Naphthalene 7.15 6.72Naphthalene 2.03 1.21 Pyrene 7.27 0.22Anthracene 3.51 4.46 Phenanthrene 9.62 3.86Pyrene 9.04 8.98 Anthracene 22.46 13.38

Group B Group BToluene 0.94 Toluene 3.71Propylbenzene 2.73 7.83 Propylbenzene 12.38 10.93Butylbenzene 4.34 3.35 Butylbenzene 20.53 3.91Pentylbenzene 5.57 1.45 Pentylbenzene 27.50 1.91

Group C Group CAniline 8.21 N,N-Diethylaniline 0.17N-Methylaniline 13.39 11.47 N-Ethylaniline 0.75 5.43N-Ethylaniline 19.90 9.05 Aniline 0.90 1.77N,N-Diethylaniline 45.39 12.87 N-Methylaniline 0.99 1.22

Group D Group Dm-Xylene 0.77 m-Xylene 4.13o-Xylene 1.08 2.57 o-Xylene 4.42 1.09p-Xylene 1.15 0.64 p-Xylene 6.46 5.81

Group E Group Eo-Cresol 0.44 o-Cresol 1.53m-Cresol 0.66 3.55 m-Cresol 1.75 1.14p-Cresol 0.91 3.45 p-Cresol 2.46 1.41

Group F Group FPyrocatechol 0.51 Pyrocatechol 1.36Resorcinol 0.53 0.05 Resorcinol 1.40 0.30

Group G Group G2,6-Dimethylphenol 0.32 2,6-Dimethylphenol 1.372,5-Dimethylphenol 0.44 1.12 2,5-Dimethylphenol 1.67 1.222,3-Dimethylphenol 0.62 1.55 2,3-Dimethylphenol 2.20 1.32

Table S3. Chromatographic data k and RS of achiral sets of analytes on coated and bonded CD-based SPs at MP composed of 40/60 MeOH/10 mM AMAC buffer, pH 4.00 (v/v)

k - retention factor, RS – resolution

Benzene

Naphthalene

Anthracene

Phenanthrene

Pyrene

Toluene

Fig. S1: Structures of analytes

Propylbenzene

Butylbenzene

Pentylbenzene

Aniline

N-Methylaniline

N-Ethylaniline

N,N-Diethylaniline

o-Xylene

m-Xylene

p-Xylene

Fig. S1: Structures of analytes

o-Cresol

m-Cresol

p-Cresol

Pyrocatechol

Resorcinol

2,3-Dimethylphenol

2,5-Dimethylphenol

2,6-Dimethylphenol

Fig. S1: Structures of analytes

N,N,N-Trimethylanilinium chloride

Benzenesulfonic acid

p-Toluenesulfonic acid