13 C NMR CDCl 3 d 1530 1472 1440 1372 1368 535 318 292 277 222 194 180 174 138

13 c nmr cdcl 3 d 1530 1472 1440 1372 1368 535 318

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13 C NMR (CDCl 3 ): d 153.0, 147.2, 144.0, 137.2, 136.8, 53.5, 31.8, 29.2, 27.7, 22.2, 19.4, 18.0, 17.4, 13.8. Electrospray MS (micrOTOF Focus) m / z (%) 207 [(C 14 H 24 N + 1] + (15), 206.19012 ([(C 14 H 24 N] + requires 206.19033, 100). 1-Butyl-3,5-dimethyl-2-pentylpyridinium bromide (7). Yield 91%. 1 H NMR (CDCl 3 ): d 9.64 (1H, s, 6-H), 7.96 (1H, s, 4- H), 4.80 (2H, dd, J 1 = 6.0 Hz, J 2 = 9.9 Hz, NCH 2 ), 2.92 (2H, dd, J 1 = 5.8 Hz, J 2 = 10.7 Hz, 1 ¢ -Pen), 2.52 (3H, s, Ar-CH 3 ), 2.50 (3H, s, Ar-CH 3 ), 1.97-1.87 (2H, m, NCH 2 C H 2 ), 1.64-1.30 (m, 8H, N(CH 2 ) 2 C H 2 , 2 ¢ ,3 ¢ ,4 ¢ -Pen), 0.96 (3H, t, J = 7.3 Hz, N(CH 2 ) 3 C H 3 ), 0.90 (3H, t, J = 7.2 Hz, 5 ¢ -Pen). 13 C NMR (CDCl 3 ): d 152.9, 147.2, 144.5, 137.1, 136.5, 57.6, 34.0, 31.8, 29.2, 27.7, 22.1, 19.7, 19.4, 18.0, 13.8, 13.6. Electrospray MS (micrOTOF Focus) m / z (%) 235 [(C 16 H 28 N) + 1] + (17), 234.22137 ([(C 16 H 28 N)] + requires 234.22163, 100). 1-Hexyl-3,5-dimethyl-2-pentylpyridinium bromide (8). Yield 85%. 1 H NMR (CDCl 3 ): d 9.76 (1H, s, 6-H), 7.89 (1H, s, 4- H), 4.85 (2H, dd, J 1 = 6.1 Hz, J 2 = 10.0 Hz, NCH 2 ), 2.93 (2H, dd, J 1 = 5.9 Hz, J 2 = 10.6 Hz, 1 ¢ -Pen), 2.56 (3H, s, Ar-CH 3 ), 2.51 (3H, s, Ar-CH 3 ), 1.95 (2H, m, NCH 2 C H 2 ), 1.61 (2H, m, 2 ¢ - Pen), 1.55–1.25 (10H, m, N(CH 2 ) 2 C H 2 C H 2 C H 2 , 2 ¢ ,3 ¢ ,4 ¢ -Pen), 0.90 (3H, t, J = 7.2 Hz, 5 ¢ -Pen), 0.84 (3H, dt, J 1 = 3.7 Hz, J 2 = 7.1 Hz, N(CH 2 ) 5 C H 3 ). 13 C NMR (CDCl 3 ): d 152.9, 147.2, 144.4, 137.1, 136.5, 57.8, 32.1, 31.8, 31.2, 29.2, 27.6, 26.0, 22.4, 22.1, 19.4, 18.0, 13.9, 13.8. Electrospray MS (micrOTOF Focus) m / z (%) 263 [(C 18 H 32 N) + 1] + (18), 262.25261 ([(C 18 H 32 N)] + requires 262.25293, 100). General procedures for the synthesis of pyridinium bis(trifluoromethanesulfonyl)imides The tetraalkylpyridinium halide (21 mmol) was dissolved in water (20 mL) and treated with an aqueous solution of bis(trifluoromethane)sulfonimide lithium salt (6,64 g, 23 mmol) in water (20 mL). The obtained solution was stirred at rt for 10 min. The product was isolated by solvent extraction using CH 2 Cl 2 (2 ¥ 10 mL). The extracts were dried over anhydrous Na 2 SO 4 and evaporated under reduced pressure to yield the required product. The ILs obtained were dried by heating at (343.15 to 353.15 K) and stirring under high vacuum (2 ¥ 10 - 1 Pa) for 48 h. 1-Hexyl-2,3,5-trimethylpyridinium bis(trifluoromethanesul- fonyl)imide (9). Yield 99%. 1 H NMR (CDCl 3 ): d 8.29 (1H, s, 6-H), 7.96 (1H, s, 4-H), 4.47 (2H, dd, J 1 = 5.9 Hz, J 2 = 10.3 Hz, NCH 2 ), 2.69 (3H, s, Ar-CH 3 ), 2.50 (3H, s, Ar-CH 3 ), 2.46 (3H, s, Ar-CH 3 ), 1.88 (2H, m NCH 2 C H 2 ), 1.43 (2H, m, N(CH 2 ) 2 C H 2 ), 1.33 (4H, m, N(CH 2 ) 3 C H 2 C H 2 ), 0.88 (3H, t, J = 7.1 Hz, N(CH 2 ) 5 C H 3 ). 13 C NMR (CDCl 3 ): d 150.6, 146.7, 142.2, 138.6, 136.3, 119.77 (q, J C-F = 321.4 Hz), 59.2, 31.0, 30.4, 25.9, 22.3, 19.9, 17.7, 16.1, 13.8. 19 F RMN (CDCl 3 ): d - 78.92. Electrospray MS (apex-Qe) m / z (%) 693.30 [(C 14 H 24 N) 2 (C 2 F 6 NO 4 S 2 ) + 1] + (4), 692.29730 ([(C 14 H 24 N) 2 (C 2 F 6 NO 4 S 2 )] + requires 692.29849, 11), 207.19 [(C 14 H 24 N) + 1] + (12), 206.19 [(C 14 H 24 N)] + (100). 2-Ethyl-1-hexyl-3,5-dimethylpyridinium bis(trifluoromethane- sulfonyl)imide (10). Yield 97%. 1 H NMR (CDCl 3 ): d 8.36 (1H, s, 6-H), 7.98 (1H, s, 4-H), 4.49 (2H, dd, J 1 = 6.1 Hz, J 2 = 10.1 Hz, NCH 2 ), 3.05 (2H, q, J = 7.6 Hz, 2-CH 2 ), 2.54 (3H, s, Ar- CH 3 ), 2.49 (3H, s, Ar-CH 3 ), 1.93 (2H, m, NCH 2 C H 2 ), 1.46 (2H, m, N(CH 2 ) 2 C H 2 ), 1.35 (7H, m, N(CH 2 ) 3 C H 2 C H 2 , 2-CH 2 C H 3 ), 0.91 (3H, t, J = 6.9 Hz, N(CH 2 ) 5 C H 3 ). 13 C NMR (CDCl 3 ): d 154.6, 147.5, 142.7, 137.8, 136.7, 119.8 (q, J C-F = 321.4 Hz), 58.4, 31.8, 31.0, 26.0, 22.7, 22.3, 19.0, 17.7, 13.8, 11.7. 19 F RMN (CDCl 3 ): d - 78.92. Electrospray MS (micrOTOF Focus) m / z (%) 722 [(C 15 H 26 N) 2 (C 2 F 6 NO 4 S 2 ) + 2] + (10), 721 [(C 15 H 26 N) 2 (C 2 F 6 NO 4 S 2 ) + 1] + (22), 720.32735 ([(C 15 H 26 N) 2 (C 2 F 6 NO 4 S 2 )] + requires 720.32979, 57), 637 [(C 26 H 39 F 6 N 3 O 4 S 2 ) + 2] + (2), 636 [(C 26 H 39 F 6 N 3 O 4 S 2 ) + 1] + (10), 221 [(C 15 H 26 N) + 1] + (18), 220 [(C 15 H 26 N)] + (100).
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