Absolute helical arrangement of stacked benzene rings: Heterogeneous double-helical interaction comprising a hydrogen-bonding belt and an offset parallel aromatic-aromatic-interaction array

Angewandte Chemie - International Edition

Volumn 43, Issue 11, 2004, Pages 1360-1363

  Azumaya, Isao ^a   Uchida, Daisuke ^b   Kato, Takako ^a   Yokoyama, Akihiro ^b   Tanatani, Aya ^b   Takayanagi, Hiroaki ^a   Yokozawa, Tsutomu ^b  

^a KITASATO UNIVERSITY   (Japan)

^b KANAGAWA UNIVERSITY   (Japan)

Author keywords

Chiral resolution; Chirality; Crystal engineering; Helical structures; Hydrogen bonds

Indexed keywords

CRYSTAL STRUCTURE; SELF ASSEMBLY; SINGLE CRYSTALS; STRUCTURE (COMPOSITION);

ACHIRAL COMPOUNDS; CHIRAL STRUCTURES; HELICAL INTERACTIONS;

BENZENE;

ARGON; AROMATIC COMPOUND; BENZENE; HYDROGEN; HYDROXYL GROUP;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION;

BENZENE; BENZENE DERIVATIVES; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 4544313767     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352788     Document Type: Article

References (70)

1. a) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011;
2. b) J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk, Chem. Rev. 2001, 101, 4039-4070;
3. c) L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097;
4. d) B. Gong, Chem. Eur. J. 2001, 7, 4336-4342;
5. e) C. Schmuck, Angew. Chem. 2003, 115, 2552-2556; Angew. Chem. Int. Ed. 2003, 42, 2448-2452.
6. e) C. Schmuck, Angew. Chem. 2003, 115, 2552-2556; Angew. Chem. Int. Ed. 2003, 42, 2448-2452.
7. G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
8. G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
9. a) C. Nuckolls, T. J. Katz, G. Katz, P. J. Collings, L. Castellanos, J. Am. Chem. Soc. 1999, 121, 79-88;
10. b) M. S. Gin, T. Yokozawa, R. B. Prince, J. S. Moore, J. Am. Chem. Soc. 1999, 121, 2643-2644;
11. c) R. B. Prince, J. G. Saven, P. G. Wolynes, J. S. Moore, J. Am. Chem. Soc. 1999, 121, 3114-3121;
12. d) W. Y. Yang, R. B. Prince, J. Sabelko, J. S. Moore, M. Gruebele, J. Am. Chem. Soc. 2000, 122, 3248-3249;
13. e) C. Kübel, M. J. Mio, J. S. Moore, D. C. Martin, J. Am. Chem. Soc. 2002, 124, 8605-8610;
14. f) D. Zhao, J. S. Moore, J. Am. Chem. Soc. 2002, 124, 9996-9997;
15. g) D. J. Hill, J. S. Moore, Proc. Natl. Acad. Sci. USA 2002, 99, 5053-5057.
16. a) T. Kawamoto, B. S. Hammes, B. Haggerty, G. P. A. Yap, A. L. Rheingold, A. S. Borovik, J. Am. Chem. Soc. 1996, 118, 285-286;
17. b) R. B. Prince, S. A. Barnes, J. S. Moore, J. Am. Chem. Soc. 2000, 122, 2758-2762;
18. c) A. Tanatani, M. J. Mio, J. S. Moore, J. Am. Chem. Soc. 2001, 123, 1792-1793;
19. d) T. Nishinaga, A. Tanatani, K. Oh, J. S. Moore, J. Am. Chem. Soc. 2002, 124, 5934-5935.
20. a) J.-M. Lehn, A. Rigault, J. Siegel, J. Harrowfield, B. Chevrier, D. Moras, Proc. Natl. Acad. Sci. USA 1987, 84, 2565-2569;
21. b) U. Koert, M. M. Harding, J.-M. Lehn, Nature 1990, 346, 339-342;
22. c) K. A. Hirsch, S. R. Wilson, J. S. Moore, Chem. Commun. 1998, 13-14;
23. d) S. J. Coles, J. G. Frey, P. A. Gale, M. B. Hursthouse, M. E. Light, K. Navakhun, G. L. Thomas, Chem. Commun. 2003, 568-569;
24. e) Y. Cui, H. L. Ngo, W. Lin, Chem. Commun. 2003, 1388-1389.
25. a) L. J. Prins, F. D. Jong, P. Timmerman, D. N. Reinhoudt, Nature 2000, 408, 181-184;
26. b) L. J. Prins, E. E. Neuteboom, V. Paraschiv, M. Crego-Calama, P. Timmerman, D. N. Reinhoudt, J. Org. Chem. 2002, 67, 4808-4820.
27. a) M. P. Lightfoot, F. S. Mair, R. G. Pritchard, J. E. Warren, Chem. Commun. 1999, 1945-1946;
28. b) S. J. Geib, C. Vicent, E. Fan, A. D. Hamilton, Angew. Chem. 1993, 105, 83-85; Angew. Chem. Int. Ed. Engl. 1993, 32, 119-121;
29. b) S. J. Geib, C. Vicent, E. Fan, A. D. Hamilton, Angew. Chem. 1993, 105, 83-85; Angew. Chem. Int. Ed. Engl. 1993, 32, 119-121;
30. c) T. B. Norsten, R. McDonald, N. R. Branda, Chem. Commun. 1999, 719-720;
31. d) P. Gangopadhyay, T. P. Radhakrishnan, Angew. Chem. 2001, 113, 2517-2521; Angew. Chem. Int. Ed. 2001, 40, 2451-2455;
32. d) P. Gangopadhyay, T. P. Radhakrishnan, Angew. Chem. 2001, 113, 2517-2521; Angew. Chem. Int. Ed. 2001, 40, 2451-2455;
33. e) A. P. H. J. Schenning, P. Jonkheijm, E. Peeters, E. W. Meijer, J. Am. Chem. Soc. 2001, 123, 409-416;
34. f) J. E. Field, D. Venkataraman, Chem. Commun. 2002, 306-307;
35. g) R. Shenhar, H. Wang, R. E. Hoffman, L. Frish, L. Avram, I. Willner, A. Rajca, M. Rabinovitz, J. Am. Chem. Soc. 2002, 124, 4685-4692;
36. h) V. Král, F. P. Schmidtchen, K. Lang, M. Berger, Org. Lett. 2002, 4, 51.
37. a) A. Tanatani, K. Yamaguchi, I. Azumaya, R. Fukutomi, K. Shudo, H. Kagechika, J. Am. Chem. Soc. 1998, 120, 6433-6442;
38. b) V. Berl, I. Huc, R. G. Khoury, M. J. Krische, J.-M. Lehn, Nature 2000, 407, 720-723;
39. c) C. Y. Li, S. Z. D. Cheng, X. Weng, J. J. Ge, F. Bai, J. Z. Zhang, B. H. Calhoun, F. W. Harris, L.-C. Chien, B. Lotz, J. Am. Chem. Soc. 2001, 123, 2462-2463.
40. a) P. Hobza, H. L. Selzle, E. W. Schlag, J. Am. Chem. Soc. 1994, 116, 3500-3506;
41. b) I. Dance, M. Scudder, J. Chem. Soc. Chem. Commun. 1995, 1039-1040;
42. c) V. E. Williams, R. P. Lemieux, G. R. J. Thatcher, J. Org. Chem. 1996, 61, 1927-1933;
43. d) C. B. Martin, H. R. Mulla, P. G. Willis, A. Cammers-Goodwin, J. Org. Chem. 1999, 64, 7802-7806;
44. e) P. Dapporto, P. Paoli, S. Roelens, J. Org. Chem. 2001, 66, 4930-4933;
45. f) K. Biradha, M. Fujita, Chem. Commun. 2001, 15-16;
46. g) S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, K. Tanabe, J. Am. Chem. Soc. 2002, 124, 104-112;
47. h) M. J. Rashkin, M. L. Waters, J. Am. Chem. Soc. 2002, 124, 1860-1861;
48. i) S. Tsuzuki, K. Honda, R. Azumi, J. Am. Chem. Soc. 2002, 124, 12200-12209;
49. j) Y. Miyake, A. Hosoda, M. Takagaki, E. Nomura, H. Taniguchi, Chem. Commun. 2002, 132-133.
50. a) T. Nakano, Y. Okamoto, Chem. Rev. 2001, 101, 4013-4038;
51. b) M. Ishikawa, K. Maeda, E. Yashima, J. Am. Chem. Soc. 2002, 124, 7448-7458;
52. c) T. Aoki, T. Kaneko, N. Maruyama, A. Sumi, M. Takahasi, T. Sato, M. Teraguchi, J. Am. Chem. Soc. 2003, 125, 6346-6347.
53. a) I. Azumaya, K. Yamaguchi, I. Okamoto, H. Kagechika, K. Shudo, J. Am. Chem. Soc. 1995, 117, 9083-9084;
54. b) I. Azumaya, I. Okamoto, S. Nakayama, A. Tanatani, K. Yamaguchi, K. Shudo, H. Kagechika, Tetrahedron 1999, 55, 11237-11246;
55. 1,2-bis(formylamino)benzene also gave chiral crystals: c) I. Azumaya, I. Okamoto, H. Takayanagi, Anal. Sci. 2003, 19, x3-x4;
56. d) I. Azumaya, T. Kato, I. Okamoto, R. Yamasaki, A. Tanatani, K. Yamaguchi, H. Kagechika, H. Takayanagi, Org. Lett. 2003, 5, 3939-3942.
57. a) R. E. Pincock, K. R. Wilson, J. Am. Chem. Soc. 1971, 93, 1291-1292;
58. b) R. E. Pincock, K. R. Wilson, J. Chem. Educ. 1973, 50, 455-457;
59. c) F. Toda, M. Yagi, S. Soda, J. Chem. Soc. Chem. Commun. 1987, 1413-1414;
60. d) H. Koshima, T. Nakagawa, T. Matsuura, H. Miyamoto, F. Toda, J. Org. Chem. 1997, 62 , 6322-6325;
61. e) M. Sakamoto, Chem. Eur. J. 1997, 3, 684-689;
62. f) B. Gong, C. Zheng, H. Zeng, J. Zhu, J. Am. Chem. Soc. 1999, 121, 9766-9767;
63. g) R. Kuroda, Y. Imai, T. Sato, Chirality 2001, 13, 588-594;
64. h) K. Asakura, T. Soga, T. Uchida, S. Osanai, D. K. Kondepudi, Chirality 2002, 14, 85-89;
65. i) M. Sakamoto, T. Iwamoto, N. Nono, M. Ando, W. Arai, T. Mino, T. Fujita, J. Org. Chem. 2003, 68, 942-946.
66. R. Kuroda, T. Honma, Chirality 2000, 12, 269-277.
67. Circular Dichroism: Principles and Applications, 2nd ed. (Eds.: N. Berova, K. Nakanishi, R. W. Woody), Wiley-VCH, Weinheim, 2000.
68. w = 0.067, GOF = 1.29 for 2781 reflections with I > 0.0σ(I). The Flack absolute structure parameter has a value of -0.041(0.174), while the inverted stereochemistry requires a value of 1.036(0.164). CCDC-218393 (1a) and CCDC-218394 (1b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
69. H. D. Flack, Acta Crystallogr. Sect. A 1983, 39, 876-881.
70. 2OC=O⋯HO- (see Supporting Information). The two other hydroxy groups form weak hydrogen bonds with carbonyl groups on the next molecule, but do not form a hydrogen-bonding array.