Encapsulated carboxylic acid dimers with compressed hydrogen bonds

Angewandte Chemie - International Edition

Volumn 50, Issue 2, 2011, Pages 528-531

  Ajami, Dariush ^b   Tolstoy, Peter M ^a   Dube, Henry ^b   Odermatt, Severin ^b   Koeppe, Benjamin ^a   Guo, Jing ^a   Limbach, Hans Heinrich ^a   Rebek Jr , Julius ^b  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

carboxylic acid dimers; host guest systems; hydrogen bonds; NMR spectroscopy; self assembled capsules

Indexed keywords

CARBOXYLIC ACID DIMERS; HOST-GUEST SYSTEM; INTERNAL PRESSURE; MOLECULAR CAPSULE; NMR SPECTROSCOPY; SELF-ASSEMBLED;

CARBOXYLIC ACIDS; DIMERS; HYDROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYDROGEN BONDS;

ACETYLENEUREA; ALKYNE; CARBOXYLIC ACID; CAVITAND; ETHER DERIVATIVE; IMIDAZOLE DERIVATIVE; RESORCINOL DERIVATIVE;

ARTICLE; CHEMISTRY; DIMERIZATION; HYDROGEN BOND; MICROCAPSULE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKYNES; CAPSULES; CARBOXYLIC ACIDS; DIMERIZATION; ETHERS, CYCLIC; HYDROGEN BONDING; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; RESORCINOLS;

EID: 78650893039     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002182     Document Type: Article

References (49)

1. J. C. Sherman, Tetrahedron 1995, 51, 3395-3422.
2. L. Avram, Y. Cohen, J. Am. Chem. Soc. 2004, 126, 11556-11563
3. A. Shivanyuk, J. Rebek,- Jr., Chem. Commun. 2001, 2424-2425.
4. J. M. C. A. Kerckhoffs, M. G. J. ten-Cate, M. A. Mateos-Timoneda, F. W. B. van-Leeuwen, B. Snellink-RuÃl, B. A. L. Spek, H. Kooijman, M. Crego-Calama, D. N. Reinhoudt, J. Am. Chem. Soc. 2005, 127, 12697-12708.
5. L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469-472.
6. T. Gerkensmeier, W. Iwanek, C. Agena, R. Fröhlich, S. Kotila, C. Näther, J. Mattay, Eur. J. Org. Chem. 1999, 2257-2262.
7. K. Kobayashi, K. Ishii, S. Sakamoto, T. Shirasaka, K. Yamaguchi, J. Am. Chem. Soc. 2003, 125, 10615-10624.
8. J. J. González, R. Ferdani, E. Albertini, J. M. Blasco, A. Arduini, A. Pochini, P. Prados, J. de-Mendoza, Chem. Eur. J. 2000, 6, 73-80.
9. A. Scarso, L. Pellizzaro, O. De-Lucchi, A. Linden, F. Fabris, Angew. Chem. 2007, 119, 5060-5063
10. Angew. Chem. Int. Ed. 2007, 46, 4972-4975.
11. M. Yoshizawa, M. Tamura, M. Fujita, Science 2006, 312, 251-254
12. M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. 2009, 121, 3470-3490
13. Angew. Chem. Int. Ed. 2009, 48, 3418-3438
14. T. Murase, S. Horiuchi, M. Fujita, J. Am. Chem. Soc. 2010, 132, 2866-2867.
15. M. Ziegler, J. L. Brumaghim, K. N. Raymond, Angew. Chem. 2000, 112, 4285-4287
16. Angew. Chem. Int. Ed. 2000, 39, 4119-4121.
17. L. S. Kaanumalle, C. L. D. Gibb, B. C. Gibb, V. Ramamurthy, J. Am. Chem. Soc. 2005, 127, 3674-3675.
18. A. Lützen, A. R. Renslo, C. A. Schalley, B. M. O'Leary, J. Rebek,- Jr., J. Am. Chem. Soc. 1999, 121, 7455-7456.
19. D. Ajami, J. Rebek,- Jr., J. Am. Chem. Soc. 2006, 128, 15038-15039.
20. D. Ajami, J. Rebek,- Jr., Angew. Chem. 2008, 120, 6148-6150
21. Angew. Chem. Int. Ed. 2008, 47, 6059-6061.
22. D. Ajami, J. Rebek,- Jr., Nat. Chem. 2009, 1, 87-90.
23. a-values of toluic acid (4.34), p-ethyl- (4.35), p-isopropyl- (4.35), and p-tert-butylbenzoic acid (4.40) indicate that differences in acidity are not the cause of the observed changes in the chemical shift.
24. P. von R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
25. D. Ajami, J. Rebek,- Jr., J. Org. Chem. 2009, 74, 6584-6591.
26. C. Detering, P. M. Tolstoy, N. S. Golubev, G. S. Denisov, H. H. Limbach, Dokl. Phys. Chem. 2001, 379, 1-4.
27. I. G. Shenderovich, H. H. Limbach, S. N. Smirnov, P. M. Tolstoy, G. S. Denisov, N. S. Golubev, Phys. Chem. Chem. Phys. 2002, 4, 5488-5497.
28. P. M. Tolstoy, P. Schah-Mohammedi, S. N. Smirnov, N. S. Golubev, G. S. Denisov, H. H. Limbach, J. Am. Chem. Soc. 2004, 126, 5621-5634.
29. "Hydrogen Bond Isotope Effects Studied by NMR":, H. H. Limbach, G. S. Denisov, N. S. Golubev, in Isotope Effects In Chemistry and Biology (Eds.:, A. Kohen, H.-H. Limbach,), Taylor & Francis, Boca Raton FL, 2005; chap.- 7, pp.- 193-230.
30. M. Pietrzak, M. F. Shibl, M. Bröring, O. Kühn, H. H. Limbach, J. Am. Chem. Soc. 2007, 129, 296-304
31. M. F. Shibl, M. Pietrzak, H. H. Limbach, O. Kühn, ChemPhysChem 2007, 8, 315-321.
32. H. H. Limbach, P. M. Tolstoy, N. Perez-Hernandez, J. Guo, I. G. Shenderovich, G. S. Denisov, Isr. J. Chem. 2009, 49, 199-216.
33. R. K. Harris, P. Jackson, L. H. Merwin, B. J. Say, G. S. Hägele, J. Chem. Soc. Faraday Trans. 1 1988, 84, 3649-3672.
34. U. Sternberg, E. L. Brunner, J. Magn. Reson. Ser. A 1994, 108, 142-150
35. E. Brunner, U. Sternberg, J. Progr. NMR Spect. 1998, 32, 21-57.
36. T. K. Mildvan, A. S. Harris, Proteins Struct. Funct. Genet. 1999, 35, 275-282.
37. "Proton chemical shift measurements in biological solids":, A. McDermott, C. F. Ridenour, in Encyclopedia of NMR, Wiley, Chichester, 1996, pp.- 3820-3825.
38. T. Emmler, S. Gieschler, H. H. Limbach, G. Buntkowsky, J. Mol. Struct. 2004, 700, 29-38.
39. T. J. Steiner, W. Saenger, Acta Crystallogr. Sect. B 1994, 50, 348-357.
40. C. C. Wilson, N. Shankland, A. J. Florence, J. Chem. Soc. Faraday Trans. 1996, 92, 5051-5057.
41. R. Feld, M. S. Lehmann, K. W. Muir, J. C. Speakmann, Z. Kristallogr. 1981, 157, 215-231.
42. D. F. Brougham, A. J. Horsewill, A. Ikram, R. M. Ibberson, P. J. McDonald, M. Pinter-Krainer, J. Chem. Phys. 1996, 105, 979-982.
43. D. Rechavi, A. Scarso, J. Rebek,- Jr., J. Am. Chem. Soc. 2004, 126, 7738-7739
44. Y. L. Zhao, K. N. Houk, D. Rechavi, A. Scarso, J. Rebek,- Jr., J. Am. Chem. Soc. 2004, 126, 11428-11429.
45. G. Gilli, P. Gilli, The Nature of the Hydrogen Bond: Outline of a Comprehensive Hydrogen Bond Theory, Oxford University Press, Oxford, 2009.
46. A. F. M. Barton, J. Chem. Educ. 1971, 48, 156-162.
47. B. N. Roy, Fundamentals of Classical and Statistical Thermodynamics, Wiley, Chichester, 2002, p.- 39.
48. W. D. Harkins, Proc. Nat. Acad. Sci. USA 1919, 5, 562-568
49. W. D. Harkins, H. H. King, J. Am. Chem. Soc. 1919, 41, 970-992.