Novel self-assembly of m-xylylene type dithioureas by head-to-tail hydrogen bonding

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7481-7489

  Tobe, Yoshito ^a   Sasaki, Shin Ichi ^a   Mizuno, Masaaki ^a   Hirose, Keiji ^a   Naemura, Koichiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001317713     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980441p     Document Type: Article

References (46)

1. (a) Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 775, 369-370.
2. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072-7080.
3. (c) Jubian, V.; Veronese, A.; Dixon, R. P.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1237-1239.
4. (d) Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron, 1995,51, 621-634.
5. For reviews: (e) Scheerder, J.; Engbersen, J. F. J.; Reinhoudt, D. N. Red. Trav. Chim. Pays-Bas 1996,115,307-320.
6. (f) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
7. (a) Nishizawa, S.; Bühlmann, P.; Iwao, M.; Umezawa, Y. Tetrahedron Lett. 1995,36, 6483-6486.
8. (b) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647-1654.
9. (a) Nowick, J. S.; Antonovich, V.; Noronha, G.; Ziller, J. W. J. Org. Chem. 1995, 60, 1888-1890.
10. (b) Shimizu, K. D.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12403-12407.
11. (c) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996,52, 8489-8496.
12. (d) Harmann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329.
13. (e) Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634.
14. (f) Etter, M. C.; Urbanczyk-Lipkowska, S.; Zia-Ebrahimi, M.; Panunto, T. W. J. Am. Chem. Soc. 1990,112,8415-8426.
15. (g) Kane, J. J.; Liao, R.-F.; Lauher, J. W.; Fowler, F. W. J. Am. Chem. Soc. 1995, 117, 12003-12004.
16. 2
17. For a preliminary report of this work, see: Tobe, Y.; Sasaki, S.; Hirose, K.; Naemura, K. Tetrahedron Lett. 1997, 38, 4791-4794.
18. (a) Jadzyn, J.; Stockhausen, M.; Zywucki, B. J. Phys. Chem. 1987, 91, 754-757.
19. (b) Scheerder, J.; Engbersen, J. F. J.; Alessandro, C.; Ungaro, R.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6448-6454.
20. Weller, L. E.; Ball, C. D.; Sell, H. M. J. Am. Chem. Soc. 1952, 74, 1104.
21. Nagasawa, A.; Kitano, H.; Fukui, K. Bull. Chem. Soc. Jpn. 1966, 39, 2434-2437.
22. Katritzky, A. R.; Moutou, J.-T.; Yang, Z. Synthesis 1995,14971505.
23. Moore, S. S.; Tarnowski, T. L.; Newcomb, M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6398-6405.
24. DuVernet, R. B.; Wennerström, O.; Lawson, J.; Otsubo, T.; Bockelheide, V. J. Am. Chem. Soc. 1978, 100, 2457-2464.
25. Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon Press: Oxford, U.K., 1969; p 104.
26. 2 protons of the butyl chain shifted upfield from δ 3.13 to 2.86. However, the signal downfield shifted to δ 2.89 when the concentration increased up to 21 mM. Such concentration dependence precluded the calculation of the association constants on the assumption that monomer-dimer equilibrium is dominant in this concentration range.
27. Horman, I.; Dreux, B. Heh. Chim. Acta 1984, 67, 754-764.
28. Karplus, M. J. Chem. Phys. 1959, 30, 11-15.
29. For the anisotropic deshielding effect of carbonyl group, see ref 12, p 88. Such large chemical shift difference of vicinal protons adjacent to an amide nitrogen is also seen in the spectra of cyclic compounds:
30. (a) Bohlmann, F.; Schumann. D. Tetrahedron Lett. 1965, 2435-2440.
31. (b) Kang, J.; Hilmersson, G.; Santamaria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650-3656.
32. (a) Martin, M. L.; Filleux-Blanchard, M. L.; Martin, G. J.; Webb, G. A. Org. Magn. Keson. 1980, 13, 396-402.
33. (b) Haushalter, K. A.; Lau, J.; Roberts, J. D. J. Am. Chem. Soc. 1996, 118, 8891-8896.
34. For calculation of the ΔG‡ value, we did not take into account the participation of monomer la in the equilibrium between 24 and 24′, because even at 90 °C the monomer-dimer equilibrium shifted almost exclusively to the dimer at this concentration. The apparent upfield shift of the chemical shift of the NH protons with increasing temperatures is ascribed to the distortion of the hydrogen bond rather than dissociation of 24. See, for the temperature effects on the chemical shift of hydrogen-bonded protons: Adrian, J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 678-680.
35. For IR studies of hydrogen bonds, see: (a) Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond: Freeman: San Francisco, CA, 1960.
36. (b) Klotz, I. M.; Franzen, J. S. J. Am. Chem. Soc. 1962,84,34613466.
37. (c) Néel, J. Pure Appl. Chem. 1972, 31, 201-225.
38. (d) Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 1054-1062.
39. Nonlinear alignment of urea groups in the solid state was found in the structure of hydrogen-bonded dimer of a calix[4]arene derivative. However, it seems likely that the exceptional hydrogen bonding pattern is due to the restricted geometry of urea functions anchored to the rigid calixarene backbone: Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, L; Vogt, W. Chem. Commun. 1996, 2533-2534.
40. Pullukat, T. J.; Urry, G. Tetrahedron Lett. 1967, 1953-1954.
41. Wenner, W. J. Org. Chem. 1952, 17, 523-528.
42. Excel version 5.0; Microsoft Corp., Tokyo.
43. Wave Metrics, Inc., Lake Oswego, NY.
44. Sheldrick, G. M. SHELXS-86, Program for Crystal Structure Determination, University of Göttingen, Germany, 1986.
45. Fan, H. SAPI91, Structure Analysis Program with Intelligent Control, Rigaku Corporation, Tokyo, Japan, 1991.
46. Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Polidori, G.; Spagna, R.; Viterbo, D. J. Appl. Crystalhgr. 1989,22,389393.