Hydrophobic encapsulation of hydrocarbon gases

Organic Letters

Volumn 9, Issue 9, 2007, Pages 1753-1755

  Leontiev, Alexander V ^a   Saleh, Anas W ^a   Rudkevich, Dmitry M ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GAS; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

GASES; HYDROCARBONS; HYDROPHOBICITY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 34248330998     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070465v     Document Type: Article

References (29)

1. (a) Cram, D. J.; Cram, J. M. Container Molecules and their Guests; Royal Society of Chemistry: Cambridge. 1994.
2. (b) Rudkevich, D. M. Bull. Chem. Soc. Jpn. 2002, 75, 393-413.
3. (c) Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
4. (d) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967.
5. (e) Collet, A.; Dutasta, J.-P.; Lozach, B.; Canceill, J. Top. Curr. Chem. 1993, 165, 103-129.
6. (f) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508.
7. (a) Rudkevich, D. M. Angew. Chem., Int. Ed. 2004, 43, 558-571.
8. (b) Rudkevich, D. M.; Leontiev, A. V. Aust. J. Chem. 2004, 57, 713-722.
9. Hydrocarbon gases have very low solubility in water (1-2 mmol/L); see: McAuliffe, C. J. Phys. Chem. 1966, 70, 1267-1275.
10. Encapsulation of hydrocarbon gases: (a) Gibb, C. L. D.; Gibb, B. C. J. Am. Chem. Sac. 2006, 128, 16498-16499.
11. (b) Nakazawa, J.; Mizuki, M.; Shimazaki, Y.; Tani, F.; Naruta, Y. Org. Lett. 2006, 8, 4275-4278.
12. (c) Nakazawa, J.; Nagiwara, J.; Mizuki, M.; Shimazaki, Y.; Tani, F.; Naruta, Y. Angew. Chem., Int. Ed. 2005, 44, 3744-3746.
13. (d) Miyahara, Y.; Abe, K.; Inazu, T. Angew. Chem., Int. Ed. 2002, 41, 3020-3023.
14. (e) Bartik, K.; Luhmer, M.; Dutasta, J.-P.; Collet, A.; Reisse, J. J. Am. Chem. Soc. 1998, 120, 784-791.
15. (f) Branda, N.; Wyler, R.; Rebek, J., Jr. Science 1994, 263, 1267-1268.
16. (g) Cram, D. J.; Tanner, M. E.; Knobler, C. B. J. Am. Chem. Soc. 1991, 113, 7717-7727.
17. Cram, D. J.; Blanda, M. T.; Pack, K.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7765-7773.
18. Suda, H.; Haraya, K. Chem. Commun. 1997, 93-94.
19. Water-soluble hemicarcerands: (a) Yoon, J.; Cram, D. Chem. Commun. 1997, 497-498.
20. (b) Piatnitski, E. L.; Flowers, R. A., II; Deshayes, K. Chem. Eur. J. 2000, 6, 999-1006.
21. (c) Singh, H.; Warmuth, R. Tetrahedron 2002, 58, 1257-1264.
22. By Cram's definition, constrictive binding works not through the intrinsic host-guest attraction but by mechanical inhibition of the decomplexation process. See ref 5.
23. Mecozzi, S.; Rebek, J., Jr. Chem. Eur. J. 1998, 4, 1016-1022.
24. Kitaigorodsky, A. I. Molecular Crystals and Molecules', Academic Press: New York, 1973; pp 18-19.
25. Shivanyuk, A.; Scarso, A.; Rebek, J., Jr. Chem. Commun. 2003, 1230-1231.
26. Thus far, attempts to characterize the hemicarceplexes by mass spectrometry (ESI-MS) have been unsuccessful.
27. Robbins, T. A.; Knobler, C. B.; Bellew, D. R.; Cram, D. J. J. Am. Chem. Soc. 1994, 116, 111-122.
28. Flammengo, R.; Wojciehowski, K.; Crego-Calama, M.; Timmerman, P.; Figoli, A.; Wessling, M.; Reinhoudt, D. N. Org. Lett. 2003, 5, 3367-3370.
29. For gas encapsulation by a hemicarcerand at the gas-solid interface, see: Leontiev, A. V.; Rudkevich, D. M. Chem. Commun. 2004, 1468-1469.