The Relationship between the Structure and Properties of Amino Acid Ionic Liquids
Abstract
:1. Introduction
2. Results and Discussion
2.1. Spectroscopic Properties
2.2. Physicochemical Properties
3. Materials and Methods
3.1. Materials
3.2. Preparation of Amino Acid Ionic Liquids
3.3. General Analytical Procedures
3.3.1. Structural Characterization of Obtained Amino Acid Ionic Liquids
3.3.2. Water Content
3.3.3. Specific Rotation
3.3.4. Viscosity
3.3.5. Thermogravimetric Analysis
3.3.6. Phase Transformations (DSC)
3.3.7. Measurement of Surface Tension
- Γmax—surface excess concentration at the saturated interface, mol·m−2,
- R—gas constant, 8.3144598(48) J·mol−1·K−1,
- T—absolute temperature, K,
- c—concentration of the salt, mol·dm−3.
- NA—the Avogadro number.
3.3.8. Cellulose Solubility
- Ccel—cellulose concentration [%],
- mcel—weight of cellulose dissolved in the ionic liquid [g],
- mcj—weight of ionic liquids [g].
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–52 are available from the authors. |
| |||
Ionic Liquid | 1H-NMR (δ/ppm) (α) | 13C-NMR (δ/ppm) (α) | C=O (2′) |
[DDTMA][Gly] | 3.09 | 44.7 | 181.7 |
[HDTMA][Gly] | 3.25 | 43.9 | 179.1 |
[TBA][l-Val]a) | 2.59 | 62.0 | 176.8 |
[tBMA][l-Val] | 2.56 | 78.7 | 176.3 |
[EMIM][l-Val] | 2.63 | 62.0 | 177.2 |
[DDA][l-Val]b) | 2.55 | 62.6 | 176.3 |
[BA][l-Val]c) | 3.38 | 63.8 | 184.2 |
[Chol][l-Val] | 2.66 | 61.5 | 177.4 |
[HDTMA][l-Val] | 3.00 | 61.6 | 180.4 |
[ODTMA][l-Val] | 3.00 | 61.7 | 180.6 |
[TBA][l-Leu]a) | 2.77 | 56.1 | 177.8 |
[tBMA][l-Leu] | 2.66 | 71.1 | 177.7 |
[EMIM][l-Leu] | 2.75 | 56.3 | 178.8 |
[DDA][l-Leu]b) | 2.78 | 62.6 | 177.7 |
[BA][l-Leu]c) | 3.22 | 64.8 | 185.7 |
[Chol][l-Leu] | 2.77 | 54.5 | 178.7 |
[DDTMA][l-Leu] | 3.25 | 54.4 | 181.4 |
[HDTMA][l-Leu] | 3.25 | 54.2 | 180.7 |
[TBA][l-Ile]a) | 2.63 | 61.8 | 176.5 |
[tBMA][l-Ile] | 2.64 | 78.1 | 176.4 |
[EMIM][l-Ile] | 2.71 | 61.7 | 177.6 |
[DDA][l-Ile]b) | 2.62 | 61.3 | 176.4 |
[BA][l-Ile]c) | 3.14 | 64.1 | 185.7 |
[Chol][l-Ile] | 2.72 | 61.0 | 177.2 |
[DDTMA][l-Ile] | 3.05 | 60.9 | 180.6 |
[HDTMA][l-Ile] | 3.09 | 61.2 | 181.8 |
[TBA][l-Thr]a) | 2.86 | 59.1 | 176.3 |
[tBMA][l-Thr] | 2.92 | 68.0 | 175.8 |
[EMIM][l-Thr] | 2.86 | 59.2 | 176.6 |
[DDA][l-Thr]b) | 2.80 | 62.6 | 175.8 |
[BA][l-Thr]c) | 3.16 | 64.2 | 183.3 |
[Chol][l-Thr] | 2.85 | 58.4 | 176.5 |
[TBA][l-His]a) | 3.02 | 56.8 | 178.9 |
[tBMA][l-His] | 3.93 | 47.0 | 176.6 |
[EMIM][l-His] | 3.05 | 56.9 | 177.1 |
[DDA][l-His]b) | 3.43 | 62.7 | 176.6 |
[BA][l-His]c) | 3.57 | 58.1 | 183.3 |
[HDTMA][l-His] | 3.41 | 52.8 | 180.4 |
[ODTMA][l-His] | 3.43 | 52.8 | 180.1 |
[TBA][l-Met]a) | 2.79 | 56.0 | 176.6 |
[EMIM][l-Met] | 2.86 | 55.5 | 176.7 |
[BA][l-Met]c) | 2.69 | 58.4 | 185.8 |
[Chol][l-Met] | 2.88 | 55.30 | 177.2 |
[DDTMA][l-Met] | 3.36 | 55.4 | 182.2 |
[HDTMA][l-Met] | 3.36 | 55.4 | 181.8 |
[ODTMA][l-Met] | 3.20 | 55.2 | 181.1 |
[TBA][l-Trp]a) | 3.40 | 58.0 | 176.9 |
[EMIM][l-Trp] | 3.44 | 56.0 | 172.2 |
[BA][l-Trp]c) | 3.40 | 56.5 | 181.2 |
[Chol][l-Trp] | 2.65 | 57.0 | 177.4 |
[HDTMA][l-Arg] | 3.27 | 55.5 | 183.2 |
[ODTMA][l-Arg] | 3.15 | 55.5 | 183.1 |
[TBA][l-Tyr] | 2.19 | 58.8 | 176.8 |
[BA][l-Tyr] | 3.45 | 58.8 | 176.8 |
Ionic Liquid | v(XH) | v(CH3-)as. | v(CH3-) | v(COO−)as. | v(COO−)sym. |
---|---|---|---|---|---|
[DDTMA][Gly] | 3600–3000 br. | 2918 | 2850 | 1578 | 1396 |
[HDTMA][Gly] | 3600–3000 br. | 2918 | 2850 | 1585 | 1407 |
[TBA][l-Val]a) | 3600–3100 br. | 2959 | 2874 | 1570 | 1397 |
[DDA][l-Val]b) | 3500–3100 br. | 2956 | 2854 | 1573 | 1397 |
[BA][l-Val]c) | 3600–3000 br. | 2957 | 2854 | 1583 | 1396 |
[Chol][l-Val]d) | 3362 | 2961 | 2874 | 1571 | 1399 |
[HDTMA][l-Val] | 3600–3000 br. | 2920 | 2851 | 1584 | 1396 |
[ODTMA][l-Val] | 3600–3000 br. | 2918 | 2849 | 1569 | 1408 |
[TBA][l-Leu]a) | 3500–3100br. | 2961 | 2875 | 1573 | 1383 |
[DDA][l-Leu]b) | 3500–3100 br. | 2925 | 2855 | 1576 | 1398 |
[BA][l-Leu]c) | 3600–3000 br. | 2954 | 2854 | 1578 | 1396 |
[Chol][l-Leu]d) | 3377 | 2956 | 2871 | 1578 | 1401 |
[DDTMA][l-Leu] | 3600–3000 br. | 2918 | 2850 | 1580 | 1395 |
[HDTMA][l-Leu] | 3600–3000 br. | 2918 | 2850 | 1580 | 1395 |
[TBA][l-Ile]a) | 3500–3100br. | 2960 | 2875 | 1574 | 1384 |
[DDA][l-Ile]b) | 3500–3100 br. | 2957 | 2855 | 1577 | 1396 |
[BA][l-Ile]c) | 3600–3000 br. | 2957 | 2854 | 1572 | 1396 |
[Chol][l-Ile]d) | 3378 | 2963 | 2876 | 1575 | 1402 |
[DDTMA][l-Ile] | 3600–3000 br. | 2918 | 2851 | 1579 | 1395 |
[HDTMA][l-Ile] | 3600–3000 br. | 2920 | 2851 | 1576 | 1395 |
[TBA][l-Thr]a) | 3600–3100br. | 2961 | 2874 | 1577 | 1396 |
[DDA][l-Thr]b) | 3500–3100 br. | 2924 | 2854 | 1578 | 1378 |
[BA][l-Thr]c) | 3600–3100 br. | 2956 | 2854 | 1575 | 1353 |
[Chol][l-Thr]d) | 3366 | 2973 | 2933 | 1577 | 1402 |
[TBA][l-His]a) | 3600–3100 br. | 2959 | 2875 | 1574 | 1398 |
[DDA][l-His]b) | 3500–3100 br. | 2905 | 2854 | 1587 | 1398 |
[BA][l-His]c) | 3600–3000 br. | 2956 | 2854 | 1574 | 1342 |
[HDTMA][l-His] | 3650–3000 br. | 2917 | 2848 | 1570 | 1417 |
[ODTMA][l-His] | 3650–3000 br. | 2918 | 2850 | 1578 | 1342 |
[TBA][l-Met]a) | 3600–3100 br. | 2958 | 2874 | 1580 | 1380 |
[BA][l-Met]c) | 3600–3100 br. | 2954 | 2853 | 1574 | 1406 |
[Chol][l-Met]d) | 3366 | 2970 | 2840 | 1579 | 1406 |
[DDTMA][l-Met] | 3600–3000 br. | 2918 | 2851 | 1581 | 1395 |
[HDTMA][l-Met] | 3700–3000 br. | 2920 | 2851 | 1581 | 1391 |
[ODTMA][l-Met] | 3700–3000 br. | 2919 | 2850 | 1582 | 1407 |
[TBA][l-Trp]a) | 3600–3100 br. | 2962 | 2875 | 1587 | 1354 |
[BA][l-Trp]c) | 3600–3100 br. | 2955 | 2854 | 1575 | 1355 |
[Chol][l-Trp]d) | 3252 | 2921 | 2874 | 1573 | 1404 |
[HDTMA][l-Arg] | 3600–3000 br. | 2917 | 2850 | 1570 | 1407 |
[ODTMA][l-Arg] | 3600–3000 br. | 2918 | 2849 | 1569 | 1408 |
[TBA][l-Tyr] | 3600–3000 br. | 2960 | 2850 | 1573 | 1383 |
[BA][l-Tyr] | 3600–3000 br. | 2925 | 2854 | 1578 | 1378 |
No. | Ionic Liquids | State at RT (Tm (°C)) | Colour | M (g mol−1) | Tg/°C | Td5%/°C | Td50%/°C | η/Pa·s 65 °C | [α]λT | [M]λT | Solubility of Cellulose |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | [DDTMA][Gly] | W | white | 303.50 | na | 160.2 ± 1.1 | 198.6 ± 1.3 | na | - | - | N |
2 | [HDTMA][Gly] | W | white | 358.61 | na | 177.4 ± 1.9 | 215.3 ± 1.8 | na | - | - | N |
3 | [TBA][l-Val] | L | colorless | 358.61 | −53.4 ± 2.1 | 150.0 ± 1.7 | 178.9 ± 1.9 | 0.148±0.031 | +4.10 | +14.7 | N |
4 | [tBMA][l-Val] | L | colorless | 314.20 | −55.8 ± 1.9 | 156.0 ± 2.0 | 189.0 ± 2.1 | 1.019±0.056 | +4.07 | +12.8 | N |
5 | [EMIM][l-Val] | L | colorless | 227.32 | −73.7 ± 1.2 | 194.6 ± 2.2 | 242.2 ± 2.0 | 1.420±0.073 | +6.16 | +14.0 | Y |
6 | [DDA][l-Val] | L | colorless | 442.78 | −23.4 ± 1.6 | 143.0 ± 1.8 | 199.5 ± 2.1 | 0.417±0.009 | +2.60 | +11.5 | N |
7 | [BA][l-Val] | L | colorless | 440.70 | −59.6 ± 1.7 | 149.5 ± 2.1 | 175.6 ± 1.8 | na | +2.69 | +11.9 | N |
8 | [Chol][l-Val] | L | colorless | 220.32 | −74.0c) | 168.9 ± 1.2 | 213.3 ± 1.4 | 372c) | +6.81 | +15.0 | Y |
9 | [HDTMA][l-Val] | W | white | 400.69 | na | 183.4 ± 1.7 | 211.8 ± 1.6 | na | +3.49 | +14.0 | N |
10 | [ODTMA][l-Val] | W | white | 429.75 | na | 177.1 ± 1.6 | 217.0 ± 1.8 | na | +2.48 | +10.7 | N |
11 | [TBA][l-Leu] | L | colorless | 372.64 | −51.8 ± 2.4 | 153.0 ± 2.1 | 183.3 ± 1.9 | 0.149 ± 0.025 | +2.44 | +9.1 | N |
12 | [tBMA][l-Leu] | L | colorless | 328.23 | −55.9 ± 2.1 | 158.8 ± 1.5 | 189.0 ± 1.7 | 0.207 ± 0.011 | +1.47 | +4.8 | N |
13 | [EMIM][l-Leu] | L | colorless | 241.35 | −60.3 ± 2.5 | 199.3 ± 1.8 | 243.8 ± 2.1 | 4.659 ± 0.073 | +2.08 | +5.0 | Y |
14 | [DDA][l-Leu] | L | colorless | 456.81 | −24.7 ± 1.9 | 134.2 ± 1.1 | 212.9 ± 0.8 | 0.596 ± 0.027 | +1.78 | +8.1 | N |
15 | [BA][l-Leu] | L | colorless | 454.73 | −55.5 ± 1.6 | 149.1 ± 0.9 | 176.0 ± 1.2 | na | +1.47 | +6.7 | N |
16 | [Chol][l-Leu] | L | colorless | 234.35 | −47.0c) | 183.8 ± 0.7 | 238.1 ± 1.5 | 476c) | +2.80 | +6.6 | Y |
17 | [DDTMA][l-Leu] | W | white | 359.61 | na | 182.3 ± 2.0 | 196.4 ± 2.4 | na | +0.96 | +3.5 | N |
18 | [HDTMA][l-Leu] | W | white | 414.71 | na | 175.7 ± 1.8 | 211.0 ± 1.4 | na | +2.96 | +12.3 | N |
19 | [TBA][l-Ile] | L | colorless | 372.64 | −53.2 ± 1.3 | 146.5 ± 1.6 | 177.8 ± 1.8 | 0.176 ± 0.032 | +3.91 | +14.6 | N |
20 | [tBMA][l-Ile] | L | colorless | 328.23 | −55.7 ± 2.1 | 157.4 ± 1.8 | 189.0 ± 1.4 | 3.880 ± 0.041 | +3.75 | +12.3 | N |
21 | [EMIM][l-Ile] | L | colorless | 241.35 | −61.8 ± 2.4 | 198.2 ± 2.2 | 246.7 ± 2.3 | 3.499 ± 0104 | +5.78 | +14.0 | Y |
22 | [DDA][l-Ile] | L | colorless | 456.81 | −23.3 ± 1.8 | 137.3 ± 2.1 | 191.5 ± 1.6 | 0.655 ± 0.028 | +2.80 | +12.8 | N |
23 | [BA][l-Ile] | L | colorless | 454.73 | −63.9 ± 1.7 | 147.3 ± 1.9 | 174.0 ± 1.5 | na | +2.54 | +11.6 | N |
24 | [Chol][l-Ile] | L | colorless | 234.35 | −47.0c) | 190.8 ± 1.3 | 239.7 ± 1.0 | 480c) | +6.07 | +14.2 | Y |
25 | [DDTMA][l-Ile] | W | white | 359.61 | na | 166.4 ± 1.9 | 193.8 ± 1.3 | na | +1.29 | +4.6 | N |
26 | [HDTMA][l-Ile] | W | white | 414.71 | na | 173.6 ± 1.7 | 207.5 ± 2.5 | na | +5.27 | +21.9 | N |
27 | [TBA][l-Thr] | L | colorless | 360.58 | −40.0 ± 2.1 | 163.0 ± 1.5 | 193.7 ± 2.1 | 0.316 ± 0.002 | -2.46 | -8.9 | N |
28 | [tBMA][l-Thr] | L | colorless | 316.17 | −47.5 ± 2.3 | 163.5 ± 1.4 | 200.9 ± 2.2 | 0.626 ± 0.038 | -1.47 | -4.6 | N |
29 | [EMIM][l-Thr] | L | colorless | 229.29 | −55.1 ± 1.4 | 169.1 ± 1.5 | 198.9 ± 1.2 | 0.129 ± 0.004 | -3.7 | -8.9 | Y |
30 | [DDA][l-Thr] | L | colorless | 444.75 | −58.7 ± 1.7 | 158.8 ± 2.1 | 204.2 ± 1.7 | 0.548 ± 0.007 | −1.78 | −7.9 | N |
31 | [BA][l-Thr] | L | colorless | 442.67 | −55.2 ± 1.3 | 153.6 ± 2.2 | 178.3 ± 1.6 | na | −2.57 | −11.4 | N |
32 | [Chol][l-Thr] | L | colorless | 222.29 | −39.0c) | 194.9 ± 1.6 | 240.2 ± 1.9 | 454c) | −3.05 | −6.8 | Y |
33 | [TBA][l-His] | S (128.5 ± 2.1) | yellow | 396.62 | −17.1 ± 1.2 | 181.6 ± 1.4 | 234.7 ± 1.5 | - | −3.90 | −15.5 | N |
34 | [tBMA][l-His] | S (58.9 ± 1.2) | yellow | 352.21 | −42.6 ± 1.5 | 173.4 ± 2.2 | 226.4 ± 2.6 | - | −3.33 | −11.7 | N |
35 | [EMIM][l-His] | W | yellow | 265.33 | −33.4 ± 2.2 | 216.4 ± 1.7 | 315.0 ± 1.2 | 0.497 ± 0.071 | −5.07 | −13.5 | Y |
36 | [DDA][l-His] | L | yellow | 480.79 | −39.0 ± 0.4 | 170.5 ± 1.4 | 249.6 ± 1.9 | 1.604 ± 0.008 | −3.62 | −17.4 | N |
37 | [BA][l-His] | L | yellow | 478.71 | −39.8 ± 0.3 | 140.3 ± 0.5 | 215.8 ± 1.3 | na | −3.89 | −18.6 | N |
38 | [HDTMA][l-His] | W | white | 438.70 | na | 171.9 ± 1.0 | 243.9 ± 1.6 | na | −6.00 | −26.3 | N |
39 | [ODTMA][l-His] | W | white | 467.76 | na | 212.2 ± 1.3 | 235.4 ± 2.1 | na | −4.92 | −23.0 | N |
40 | [TBA][l-Met] | L | pale yellow | 390.67 | −57.9 ± 1.1 | 155.3 ± 1.8 | 185.0 ± 2.1 | na | +1.20 | +4.7 | N |
41 | [EMIM][l-Met] | L | yellow | 259.38 | −57.0 ± 1.7 | 194.0 ± 2.1 | 238.0 ± 1.6 | na | +1.41 | +3.7 | Y |
42 | [BA][l-Met] | L | colorless | 472.76 | −61.0 ± 1.5 | 148.5 ± 1.9 | 183.1 ± 1.3 | na | +2.01 | +9.5 | N |
43 | [Chol][l-Met] | W | pale yellow | 252.38 | −61.0c) | 179.9 ± 1.3 | 213.1 ± 1.6 | 330c) | +2.30 | +5.8 | Y |
44 | [DDTMA][l-Met] | W | white | 377.64 | na | 170.3 ± 2.4 | 195.5 ± 1.9 | na | +4.00 | +15.1 | N |
45 | [HDTMA][l-Met] | W | white | 432.76 | na | 173.6 ± 1.7 | 214.6 ± 1.5 | na | +1.28 | +5.6 | N |
46 | [ODTMA][l-Met] | W | white | 461.81 | na | 176.7 ± 0.4 | 224.9 ± 1.3 | na | +0.65 | +3.0 | N |
47 | [TBA][l-Trp] | S (129.6 ± 2.3) | creamy beige | 445.68 | - | 181.7 ± 1.8 | 234.2 ± 0.9 | - | ch−13.1a) | -−58.4a) | N |
48 | [EMIM][l-Trp] | L | brown | 314.40 | −31.0 ± 2.1 | 191.5 ± 2.5 | 310.4 ± 2.1 | na | −1.65 | −5.2 | Y |
49 | [BA][l-Trp] | W | brown | 527.78 | −28.3 ± 1.9 | 145.0 ± 2.3 | 206.3 ± 1.7 | na | −2.54 | −13.4 | N |
50 | [Chol][l-Trp] | L | dark brown | 307.40 | −12.0c) | 187.6 ± 1.2 | 239.2 ± 1.8 | 5640c) | −2.55 | −7.8 | Y |
51 | [HDTMA][l-Arg] | W | white | 457.74 | na | 184.4 ± 1.4 | 252.5 ± 1.6 | na | +6.34 | +29.0 | N |
52 | [ODTMA][l-Arg] | W | white | 486.80 | na | 186.9 ± 2.1 | 235.6 ± 2.0 | na | +4.34 | +21.1 | N |
Ionic Liquids | Water (9.0) | Acetone (5.4) | Ethanol (5.2) | Chloroform (4.4) | Ethyl Acetate (4.3) | Benzene (3.0) | Diethyl Ether (2.9) | N–Hexane (0.0) |
---|---|---|---|---|---|---|---|---|
[DDTMA][Gly] | m | p | p | i | i | i | i | i |
[HDTMA][Gly] | m | p | p | i | i | i | i | i |
[TBA][l-Val] | m | m | m | m | m | i | i | i |
[tBMA][l-Val] | m | m | m | m | m | i | i | i |
[EMIM][l-Val] | m | m | m | m | m | i | i | i |
[DDA][l-Val] | m | m | m | m | m | i | i | i |
[BA][l-Val] | m | m | m | m | m | i | i | i |
[Chol][l-Val] | m | m | m | m | m | i | i | i |
[HDTMA][l-Val] | m | p | p | i | i | i | i | i |
[ODTMA][l-Val] | m | m | m | i | i | i | i | i |
[TBA][l-Leu] | m | m | m | m | m | i | i | i |
[tBMA][l-Leu] | m | m | m | m | m | i | i | i |
[EMIM][l-Leu] | m | m | m | m | m | i | i | i |
[DDA][l-Leu] | m | m | m | m | m | i | i | i |
[BA][l-Leu] | m | m | m | m | m | i | i | i |
[Chol][l-Leu] | m | m | m | m | m | i | i | i |
[DDTMA][l-Leu] | m | m | m | m | i | i | i | i |
[HDTMA][l-Leu] | m | m | m | m | i | i | i | i |
[TBA][l-Ile] | m | m | m | m | m | i | i | i |
[tBMA][l-Ile] | m | m | m | m | m | i | i | i |
[EMIM][l-Ile] | m | m | m | m | m | i | i | i |
[DDA][l-Ile] | m | m | m | m | m | i | i | i |
[BA][l-Ile] | m | m | m | m | m | i | i | i |
[Chol][l-Ile] | m | m | m | m | m | i | i | i |
[DDTMA][l-Ile] | m | m | m | m | i | i | i | i |
[HDTMA][l-Ile] | m | m | m | m | i | i | i | i |
[TBA][l-Thr] | m | m | m | p | m | i | i | i |
[tBMA][l-Thr] | m | m | m | m | m | i | i | i |
[EMIM][l-Thr] | m | m | m | m | m | i | i | i |
[DDA][l-Thr] | m | m | m | m | m | i | i | i |
[BA][l-Thr] | m | m | m | m | m | i | i | i |
[Chol][l-Thr] | m | m | m | m | m | i | i | i |
[TBA][l-His] | m | m | m | m | p | i | i | i |
[tBMA][l-His] | m | m | m | p | p | i | i | i |
[EMIM][l-His] | m | m | m | m | m | i | i | i |
[DDA][l-His] | m | m | m | m | p | i | i | i |
[BA][l-His] | m | m | m | m | m | i | i | i |
[HDTMA][l-His] | m | m | p | i | i | i | i | i |
[ODTMA][l-His] | m | m | m | i | i | i | i | i |
[TBA][l-Met] | m | m | m | m | m | i | i | i |
[EMIM][l-Met] | m | m | m | m | m | i | i | i |
[BA][l-Met] | m | m | m | m | m | i | i | i |
[Chol][l-Met] | m | m | m | m | m | i | i | i |
[DDTMA][l-Met] | m | m | m | m | i | i | i | i |
[HDTMA][l-Met] | m | m | m | m | i | i | i | i |
[ODTMA][l-Met] | m | m | m | i | i | i | i | i |
[TBA][l-Trp] | m | m | m | p | p | i | i | i |
[EMIM][l-Trp] | m | m | m | m | m | i | i | i |
[BA][l-Trp] | m | m | m | m | m | i | i | i |
[Chol][l-Trp] | m | m | m | p | p | i | i | i |
[TBA][l-Tyr] | m | m | m | m | m | i | i | i |
[BA][l-Tyr] | m | m | m | m | m | i | i | i |
[HDTMA][l-Arg] | m | p | m | i | i | i | i | i |
[ODTMA][l-Arg] | m | m | m | i | i | i | i | i |
IL | CMC (mmol·L−1) | ϒCMC (mN·m−1) | Γmax·106 (mol·m−2) | Amin·10−19 (m2) | pC20 (mmol·L−1) |
---|---|---|---|---|---|
[DDA][l-Val]a) | 0.64 | 28.3 | 3.302 | 5.186 | 0.029 |
[DDA][l-Leu]a) | 0.61 | 27.9 | 3.364 | 4.936 | 0.021 |
[DDA][l-Ile]a) | 0.60 | 28.0 | 3.373 | 4.932 | 0.014 |
[DDA][l-Thr]a) | 0.87 | 28.2 | 2.922 | 5.683 | 0.018 |
[DDA][l-His]a) | 0.82 | 29.4 | 3.071 | 5.407 | 0.025 |
[BA][l-Val]b) | 0.28 | 32.3 | 4.853 | 3.423 | 0.056 |
[BA][l-Leu]b) | 0.25 | 32.9 | 5.645 | 2.943 | 0.063 |
[BA][l-Ile]b) | 0.26 | 32.8 | 5.654 | 2.938 | 0.062 |
[BA][l-Thr]b) | 0.31 | 32.8 | 7.151 | 2.322 | 0.048 |
[BA][l-His]b) | 0.28 | 34.1 | 5.604 | 2.964 | 0.061 |
[BA][l-Met]b) | 0.25 | 34.8 | 11.751 | 1.414 | 0.055 |
[BA][l-Trp]b) | 0.34 | 33.7 | 7.463 | 2.226 | 0.068 |
[DDTMA][Gly] | 12.26 | 40.3 | 5.471 | 3.035 | 6.386 |
[DDTMA][l-Leu] | 11.81 | 40.3 | 5.273 | 3.103 | 3.621 |
[DDTMA][l-Ile] | 12.17 | 40.2 | 5.283 | 3.143 | 3.599 |
[DDTMA][l-Met] | 12.09 | 40.4 | 7.561 | 2.196 | 2.645 |
[HDTMA][Gly] | 0.78 | 41.3 | 5.273 | 3.149 | 0.356 |
[HDTMA][l-Val] | 0.78 | 41.7 | 8.157 | 2.036 | 0.316 |
[HDTMA][l-Leu] | 0.76 | 40.8 | 5.663 | 2.892 | 0.271 |
[HDTMA][l-Ile] | 0.74 | 40.7 | 5.753 | 2.887 | 0.264 |
[HDTMA][l-Met] | 0.86 | 41.8 | 4.179 | 3.974 | 0.187 |
[HDTMA][l-His] | 0.96 | 41.7 | 5.870 | 2.829 | 0.372 |
[HDTMA][l-Arg] | 1.09 | 41.7 | 8.040 | 2.065 | 0.165 |
[ODTMA][l-Val] | 0.53 | 40.2 | 3.281 | 5.062 | 0.015 |
[ODTMA][l-Met] | 0.52 | 40.3 | 2.503 | 6.635 | 0.007 |
[ODTMA][l-His] | 0.50 | 42.0 | 2.903 | 5.720 | 0.011 |
[ODTMA][l-Arg] | 0.61 | 40.1 | 3.492 | 4.755 | 0.008 |
Ionic Liquid | Cellulose (mg g−1) |
---|---|
[EMIM][l-Val] | 21.6 (60 °C) |
[EMIM][l-Leu] | 34.4 (60 °C) |
[EMIM][l-Ile] | 13.7 (60 °C) |
[EMIM][l-Thr] | 43.2 (60 °C) |
[EMIM][Cl] | 31.4 (85 °C) |
[Chol][l-Val]a) | <5 (90 °C) |
[Chol][l-Leu]a) | <5 (90 °C) |
[Chol][l-Ile]a) | <5 (90 °C) |
[Chol][l-Thr]a) | <5 (90 °C) |
[Chol][l-His]a) | <5 (90 °C) |
[Chol][l-Met]a) | <5 (90 °C) |
[Chol][l-Trp]a) | <5 (90 °C) |
[Chol][l-Tyr]a) | <5 (90 °C) |
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Ossowicz, P.; Klebeko, J.; Roman, B.; Janus, E.; Rozwadowski, Z. The Relationship between the Structure and Properties of Amino Acid Ionic Liquids. Molecules 2019, 24, 3252. https://doi.org/10.3390/molecules24183252
Ossowicz P, Klebeko J, Roman B, Janus E, Rozwadowski Z. The Relationship between the Structure and Properties of Amino Acid Ionic Liquids. Molecules. 2019; 24(18):3252. https://doi.org/10.3390/molecules24183252
Chicago/Turabian StyleOssowicz, Paula, Joanna Klebeko, Barbara Roman, Ewa Janus, and Zbigniew Rozwadowski. 2019. "The Relationship between the Structure and Properties of Amino Acid Ionic Liquids" Molecules 24, no. 18: 3252. https://doi.org/10.3390/molecules24183252
APA StyleOssowicz, P., Klebeko, J., Roman, B., Janus, E., & Rozwadowski, Z. (2019). The Relationship between the Structure and Properties of Amino Acid Ionic Liquids. Molecules, 24(18), 3252. https://doi.org/10.3390/molecules24183252