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. 2019 Oct 1;1(11):4207–4237. doi: 10.1039/c9na00308h

Example cationic counterions used in hydrophobic ion pairing.

Name Structure Mol. wt. pKa log P Paired with
Arginine-hexadecanoyl ester (AHE) graphic file with name c9na00308h-u32.jpg 398.6 0.19 Daptomycin41
Heparin41
Arginine-nonyl ester (ANE) graphic file with name c9na00308h-u33.jpg 300.5 −0.06 Daptomycin41
Heparin41
Benethamine(N-benzyl-2-phenylethanamine) graphic file with name c9na00308h-u34.jpg 211.3 3.6 Retinoic acid65,108,115
Chitosan graphic file with name c9na00308h-u35.jpg Varies Insulin53
Dodecylamine (laurylamine) graphic file with name c9na00308h-u36.jpg 185.3 10.6 5.2 Retinoic acid46,107,114
Hexadecyl trimethylammonium(cetrimonium) bromide (CTAB) graphic file with name c9na00308h-u37.jpg 364.5 2.69 Ovalbumin39
Pemetrexed103
Poly(I:C)39
Maprotiline graphic file with name c9na00308h-u38.jpg 277.4 10.5 5.1 Retinoic acid115
N α-Deoxycholyl-l-lysyl-methylester graphic file with name c9na00308h-u39.jpg 534.8 3.8 Pemetrexed4
N,N′-Dibenzyl ethylenediamine(benzathine) graphic file with name c9na00308h-u40.jpg 240.3 2.86 α-Lipoic acid47
N,N-Dimethyl dodecylamine (DDA) graphic file with name c9na00308h-u41.jpg 213.4 9.97 5.91 Am80 (ref. 40)
N,N-Dimethyl hexylamine graphic file with name c9na00308h-u42.jpg 129.2 10.4 2.72 Am80 (ref. 40)
N,N-Dimethyl octadecylamine(dimethyl stearamine) graphic file with name c9na00308h-u43.jpg 297.6 8.8 Am80 (ref. 40)
Stearylamine(octadecylamine) graphic file with name c9na00308h-u44.jpg 269.5 10.7 7.7 Retinoic acid46,65,107,114
Tetrabutyl ammonium bromide (TBAB) graphic file with name c9na00308h-u45.jpg 322.4 2.1 Bromothymol blue66
Rose bengal66
Tetraheptyl ammonium bromide (THA) graphic file with name c9na00308h-u46.jpg 490.7 8.16 Isoniazid methanesulfonate179
Tetrahexyl ammonium bromide graphic file with name c9na00308h-u47.jpg 434.6 6.16 Bromothymol blue66
Rose bengal66
Tetraoctyl ammonium bromide (TOAB) graphic file with name c9na00308h-u48.jpg 546.7 9.16 Bromothymol blue66
Rose bengal66
Tetrapentyl ammonium bromide (TPA) graphic file with name c9na00308h-u49.jpg 378.5 4.14 Isoniazid methanesulfonate179
Triethylamine (TEA) graphic file with name c9na00308h-u50.jpg 101.2 10.8 1.65 Retinoic acid46,65,107,114