Amino acid ionic liquids

Accounts of Chemical Research

Volumn 40, Issue 11, 2007, Pages 1122-1129

  Ohno, Hiroyuki ^a   Fukumoto, Kenta ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ETHYL 3 METHYLIMIDAZOLIUM; 1-ETHYL-3-METHYLIMIDAZOLIUM; AMINO ACID; IMIDAZOLE DERIVATIVE; IONIC LIQUID; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHASE TRANSITION; TEMPERATURE; TIME;

AMINO ACIDS; IMIDAZOLES; IONIC LIQUIDS; MOLECULAR STRUCTURE; PHASE TRANSITION; TEMPERATURE; TIME FACTORS; WATER;

EID: 37349005208     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700053z     Document Type: Article

References (44)

1. (a) Wilkes, J. S.;Zaworotko, M. J. Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids. J. Chem. Soc., Chem. Commun. 1992, 965-967.
2. (b) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
3. (c) Ohno, H., Ed. Electrochemical Aspects of Ionic Liquids; Wiley-Interscience: New York, 2005.
4. Earle, M. J.; Esperança, J. M. S. S.; Manuela, A. G.; Lopes, J. N. C.; Rebelo, L. P. N.; Magee, J. W.; Seddon, K. R.; Widegren, J. A. The distillation and volatility of ionic liquids. Nature 2006, 439, 381-384.
5. MacFarlane, D. R.; Golding, J.; Forsyth, S.; Forsyth, M.; Deacon, G. B. Low viscosity ionic liquids based on organic salts of the dicyanamide anion. Chem. Commun. 2001, 1430-1431.
6. Pretti, C.; Chiappe, C.; Pieraccini, D.; Gregori, M.; Abramo, F.; Monnia, G.; Intorre, L. Acute toxicity of ionic liquids to the zebrafish. Green Chem. 2006, 8, 238-240.
7. (a) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H., Jr.; Rogers, R. D. Task-specific ionic liquids for the extraction of metal ions from aqueous solutions. Chem. Commun. 2001, 135-136.
8. 2 Capture by a Task-Specific Ionic Liquid. J. Am. Chem. Soc. 2002, 124, 926-927.
9. + based on room-temperature ionic liquids containing monoaza-substituted crown ethers. Anal. Chem. 2004, 76, 2773-2779.
10. Fukumoto, K.; Yoshizawa, M.; Ohno, H. Room temperature ionic liquids from 20 natural amino acids. J. Am. Chem. Soc. 2005, 127, 2398-2399.
11. (a) Tao, G. He, L.; Sun, N.; Kou, Y. New generation ionic liquids: cations derived from amino acids. Chem. Commun. 2005, 3562-3564.
12. (b) Bao, W.; Wang, Z.; Li, Y. Synthesis of chiral ionic liquids from natural amino acids. J. Org. Chem. 2003, 68, 591-593.
13. (c) Guillen, F.; Brégeon, D.; Plaquevent, J.-C. (S)-Histidine: the ideal precursor for a novel family of chiral aminoacid and peptidic ionic liquids. Tetrahedron. Lett. 2006, 47, 1245-1248.
14. (d) Branco, L. C.; Gois, P. M. P.; Lourenço, N. M. T.; Kurteva, V. B.; Afonso, C. A. M. Simple transformation of crystalline chiral natural anions to liquid medium and their use to induce chirality. Chem. Commun. 2006, 2371-2372.
15. (e) Luo, S.; Zu, D.; Yue, H.; Wang, L.; Yang, W.; Xu, Z. Synthesis and properties of novel chiral-amine-functionalized ionic liquids. Tetrahedron: Asymmetry 2006, 17, 2028-2033.
16. Gathergood, N.; Garcia, M. T.; Scammells, P. J. Biodegradable ionic liquids: Part I. Concept, preliminary targets and evaluation. Green Chem. 2004, 6, 166-175.
17. Docherty, K. M.; Kulpa, C. F., Jr. Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem. 2005, 7, 185-189.
18. Seddon, K. R.; Stark, A.; Torres, M.-J. Influence of chloride, water, and organic solvents on the physical properties of ionic liquids. Pure Appl. Chem. 2000, 72, 2275-2287.
19. Xu, W.; Cooper, E. I.; Angell, C. Ionic liquids: ion mobilities, glass temperatures, and fragilities. J. Phys. Chem. B 2003, 107, 6170-6178.
20. (a) Ohno, H.; Yoshizawa, M. Ion conductive characteristics of ionic liquids prepared by neutralization of alkylimidazoles. Solid State Ionics 2002, 154-155, 303-309.
21. (b) Hirao, M.; Sugimoto, H.; Ohno, H. Preparation of novel room temperature molten salts by neutralization of amines. J. Electrochem. Soc. 2000, 147, 4168-4172.
22. Mizmo, T.; Marwanta, E.; Matsumi, N.; Ohno, H. Allylimidazolium halides as novel room temperature ionic liquids. Chem. Lett. 2004, 33, 1360-1361.
23. Kagimoto, J.; Fukumoto, K.; Ohno, H. Effect of tetrabutylphosphonium cation on the physico-chemical properties of amino-acid ionic liquids. Chem. Commun. 2006, 2254-2256.
24. Crowhurst, L.; Lancaster, N. L.; Arlandis, J. M. P.; Welton, T. Manipulating solute nucleophilicity with room temperature ionic liquids. J. Am. Chem. Soc. 2004, 126, 11549-11555.
25. (a) Poole, C. F. Chromatographic and spectroscopic methods for the determination of solvent properties of room temperature ionic liquids. J. Chromatogr. A 2004, 1037, 49-82.
26. (b) Anderson, J. L.; Ding, J.; Welton, T.; Armstrong, D. W. Characterizing ionic liquids on the basis of multiple solvation interactions. J. Am. Chem. Soc. 2002, 124, 14247-14254.
27. T(30) and Kamlet-Taft polarity scales. Green Chem. 2002, 4, 165-169.
28. (a) Swatloski, R. P.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D. Dissolution of cellulose with ionic liquids. J. Am. Chem. Soc. 2002, 124, 4974-4975.
29. (b) Fukaya, Y.; Sugimoto, A.; Ohno, H. Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkyl- imidazolium formates. Biomacromolecules 2006, 7, 3295-3297.
30. (a) Ding, J.; Armstrong, D. W. Chiral ionic liquids: synthesis and applications. Chirality 2005, 17, 281-292.
31. (b) Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumontb, A.; Plaquevent, J. Ionic liquids and chirality: opportunities and challenges. Tetrahedron: Asymmetry 2003, 14, 3081-3093.
32. Fukumoto, K.; Kohno, Y.; Ohno, H. Chiral stability of phosphonium-type amino acid ionic liquids. Chem. Lett. 2006, 35, 1252-1253.
33. Fukumoto, K.; Ohno, H. Design and synthesis of hydrophobic and chiral anions from amino acids as precursor for functional ionic liquids. Chem. Commun. 2006, 3081-3083.
34. Del Sesto, R. E.; Corley, C.; Robertson, A.; Wilkes, J. S. Tetraalkylphosphonium-based ionic liquids. J. Organomet. Chem. 2005, 690, 2536-2542.
35. Jacquemin, J.; Husson, P.; Padua, A. A. H.; Majer, V. Density and viscosity of several pure and water-saturated ionic liquids. Green Chem. 2006, 8, 172-180.
36. Ogihara, W.; Aoyama, T.; Ohno, H. Polarity measurement for ionic liquids containing dissociable protons. Chem. Lett. 2004, 33, 1414-1415.
37. Fukumoto, K.; Ohno, H. LCST type phase changes of mixture of water and ionic liquids derived from amino acids. Angew. Chem., Int. Ed. 2007, 46, 1852-1855.
38. Tanaka, T. Collapse of gels and the critical endpoint. Phys. Rev. Lett. 1978, 40, 820-823.
39. Kohler, F.; Rice, O. K. Coexistence curve of the triethylamine-water system. J. Chem. Phys. 1957, 26, 1614-1618.
40. (a) Lachwa, J.; Szydłowski, J.; Makowska, A.; Seddon, K. R.; Esperanc, J. M. S. S.; Guedesa, H. J. R.; Rebelo, L. P. N. Changing from an unusual high-temperature demixing to a UCST-type in mixtures of 1-alkyl-3-methylimidazolium bis{(trifluoromethyl) - sulfonyl}amide and arenas. Green Chem. 2006, 8, 262-267.
41. (b) Wagner, M.; Stanga, O.; Schröer, W. The liquid-liquid coexistence of binary mixtures of the room temperature ionic liquid 1-methyl-3-hexylimidazolium tetrafluoroborate with alcohols. Phys. Chem. Chem. Phys. 2004, 6, 4421-4431.
42. Arce, A.; Earle, M. J.; Katdare, S. P.; Rodríguez, H.; Seddon, K. R. Mutually immiscible ionic liquids. Chem. Commun. 2006, 2548-2550.
43. (a) Ohno, H.; Suzuki, C.; Fukumoto, K.; Yoshizawa, M.; Fujita, K. Electron transfer process of poly(ethylene oxide) modified cytochrome c in imidazolium type ionic liquid. Chem. Lett. 2003, 32, 450-451.
44. (b) Wiwatchaiwong, S.; Matsumura, H.; Nakamura, N.; Yohda, M.; Ohno, H. Stability of thermophilic cytochrome P450 modified with poly(ethylene oxide) in ionic liquid. Chem. Lett. 2006, 35, 798-799.