Chirality-dependent sublimation of α-(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers

Journal of Fluorine Chemistry

Volumn 131, Issue 4, 2010, Pages 495-504

  Albrecht, Merwe ^a   Soloshonok, Vadim A ^b,c   Schrader, Lena ^a   Yasumoto, Manabu ^d   Suhm, Martin A ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF OKLAHOMA   (United States)

^c INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^d CENTRAL GLASS CO LTD   (Japan)

Author keywords

Chirality; Dimer; Eutectic; Infrared; Racemate; Sublimation

Indexed keywords

EID: 77949485155     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.11.015     Document Type: Article

References (40)

1. Jacques J., Collet A., and Wilen S.H. Enantiomers, Racemates, and Resolutions (1981), John Wiley and Sons
2. Cintas P. Angew. Chem. Int. Ed. 47 (2008) 2918-2920
3. Ushio T., Tamura R., Takahashi H., Azuma N., and Yamamoto K. Angew. Chem. Int. Ed. Engl. 35 (1996) 2372-2374
4. Hayashi Y., Matsuzawa M., Yamaguchi J., Yonehara S., Matsumoto Y., Shoji M., Hashizume D., and Koshino H. Angew. Chem. Int. Ed. 45 (2006) 4593-4597
5. Breslow R., and Levine M.S. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 12979-12980
6. Diter P., Taudien S., Samuel O., and Kagan H.B. J. Org. Chem. 59 (1994) 370-373
7. Soloshonok V.A., and Berbasov D.O. Chim. Oggi/Chem. Today 24 (2004) 44-47
8. Nieminen V., Murzin D.Y., and Klika K.D. Org. Biomol. Chem. 7 (2009) 537-542
9. Pracejus G. Liebigs Ann. Chem. 622 (1959) 10-22
10. Kwart H., and Hoster D.P. J. Org. Chem. 32 (1967) 1867-1870
11. Garin D.L., Cooke Greco F.J., and Kelly L. J. Org. Chem. 42 (1977) 1249-1251
12. Perry R.H., Wu C., Nefliu M., and Cooks R.G. Chem. Commun. (2007) 1071-1073
13. Fletcher S.P., Jagt R.B.C., and Feringa B.L. Chem. Commun. (2007) 2578-2580
14. Soloshonok V.A., Ueki H., Yasumoto M., Mekala S., Hirschi J.S., and Singleton D.A. J. Am. Chem. Soc. 129 (2007) 12112-12113
15. Kuroda R., and Mason S.F. J. Chem. Soc., Dalton Trans. (1979) 273-278
16. Mastai Y., Völkel A., and Cölfen H. J. Am. Chem. Soc. 130 (2008) 2426-2427
17. Nerdel F., and Diepers W. Tetrahedron Lett. 18 (1962) 783-786
18. Koppenhoefer B., and Trettin U. Fresenius Z. Anal. Chem. 333 (1989) 750
19. Katagiri T., Yoda C., Furuhashi K., Ueki K., and Kubota T. Chem. Lett. 25 (1996) 115-116
20. Blackmond D.G., and Klussmann M. Chem. Commun. (2007) 3990-3996
21. Perlovich G.L., Kurkov S.V., Hansen L.K., and Bauer-Brandl A. J. Pharm. Sci. 93 (2004) 654-666
22. Zehnacker A., and Suhm M.A. Angew. Chem. Int. Ed. 47 (2008) 6970-6992
23. Xue Z., and Suhm M.A. J. Chem. Phys. 131 (2009) 054301
24. Su Z., Borho N., and Xu Y. J. Am. Chem. Soc. 128 (2006) 17126-17131
25. Florio G.M., Sibert III E.L., and Zwier T.S. Faraday Discuss. 118 (2001) 315-330
26. Prigogine I., and Defay R. Chemische Thermodynamik (1962), VEB, Leipzig
27. Farina M. J. Incl. Phenom. Mol. Recognit. Chem. 14 (1992) 101-111
28. Groh J. Ber. Dtsch. Chem. Ges 45 (1912) 1441-1447
29. Chickos J.S., Garin D.L., Hitt M., and Schilling G. Tetrahedron 37 (1981) 2255-2259
30. Cézard C., Rice C.A., and Suhm M.A. J. Phys. Chem. A 110 (2006) 9839-9848
31. Albrecht M., Rice C.A., and Suhm M.A. J. Phys. Chem. A 112 (2008) 7530-7542
32. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revisions B.04 and C.02, Gaussian Inc., Pittsburgh PA, 2003.
33. Borho N., Suhm M.A., Le Barbu-Debus K., and Zehnacker A. Phys. Chem. Chem. Phys. 8 (2006) 4449-4460
34. Häber T., Schmitt U., Emmeluth C., and Suhm M.A. Faraday Discuss. 118 (2001) 331-359
35. Borba A., Gómez-Zavaglia A., Lapinski L., and Fausto R. Phys. Chem. Chem. Phys. 6 (2004) 2101-2108
36. Jarmelo S., and Fausto R. Phys. Chem. Chem. Phys. 4 (2002) 1555-1563
37. Borho N., and Suhm M.A. Org. Biomol. Chem. 1 (2003) 4351-4358
38. In: Simonyi M. (Ed). Problems and Wonders of Chiral Molecules (1990), Akademiai Kiado, Budapest
39. Pérez-García L., and Amabilino D.B. Chem. Soc. Rev. 36 (2007) 941-967
40. Adler T.B., Borho N., Reiher M., and Suhm M.A. Angew. Chem. Int. Ed. 45 (2006) 3440-3445