Unusual conformational preference of an aromatic secondary urea: Solvent-dependent open-closed conformational switching of N,N′-bis(porphyrinyl)urea

Chemical Communications

Volumn 49, Issue 23, 2013, Pages 2290-2292

  Matsumura, Mio ^a   Tanatani, Aya ^a   Azumaya, Isao ^b   Masu, Hyuma ^c   Hashizume, Daisuke ^d   Kagechika, Hiroyuki ^e   Muranaka, Atsuya ^d   Uchiyama, Masanobu ^d,f  

^a OCHANOMIZU UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^c CHIBA UNIVERSITY   (Japan)

^d RIKEN   (Japan)

^e TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^f UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; N,N' BIS(2,3,7,8,12,13,17,18 OCTAETHYLPORPHYRIN 5 YL)UREA; N,N' BIS(PORPHYRINYL)UREA; PORPHYRIN; UNCLASSIFIED DRUG; UREA;

ARTICLE; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLIZATION; ELECTROCHEMICAL ANALYSIS; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVENT EFFECT;

EID: 84875964221     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc37583d     Document Type: Article

References (32)

1. N. Volz, J. Clayden, Angew. Chem., Int. Ed. 2011, 50, 12148
2. L. Fischer, G. Guichard, Org. Biomol. Chem. 2010, 8, 3101
3. F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 380
4. V. Böhmer, D. Meshcheryakov, I. Thondorf, M. Bolte, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2004, 60, 0136
5. H. Zitt, I. Dix, H. Hopf, P. G. Jones, Eur. J. Org. Chem. 2002, 2298
6. D. Meshcheryakov, F. Arnaud-Neu, V. Böhmer, M. Bolte, V. Hubscher-Bruder, E. Jobin, I. Thondorf, S. Werner, Org. Biomol. Chem. 2008, 6, 1004
7. O. Molokanova, A. Bogdan, M. O. Vysotsky, M. Bolte, T. Ikai, Y. Okamoto, V. Böhmer, Chem.Eur. J. 2007, 13, 6157
8. D. Meshcheryakov, V. Böhmer, M. Bolte, V. Hubscher-Bruder, F. Arnaud-Neu, Chem.Eur. J. 2009, 15, 4811
9. W. Dannecker, J. Kopf, H. Rust, Cryst. Struct. Commun. 1979, 8, 429
10. P. Ganis, G. Avitabile, E. Benedetti, C. Pedone, M. Goodman, Proc. Natl. Acad. Sci. U. S. A. 1970, 67, 426
11. U. Lepore, G. Castronuovo Lepore, P. Ganis, G. Germain, M. Goodman, J. Org. Chem. 1976, 41, 2134
12. K. Yamaguchi, G. Matsumura, H. Kagechika, I. Azumaya, Y. Ito, A. Itai, K. Shudo, J. Am. Chem. Soc. 1991, 113, 5474
13. A. Tanatani, H. Kagechika, I. Azumaya, R. Fukutomi, Y. Ito, K. Yamaguchi, K. Shudo, Tetrahedron Lett. 1997, 38, 4425
14. T. L. Kurth, F. D. Lewis, J. Am. Chem. Soc. 2003, 125, 13760
15. G. B. D. Santos, F. D. Lewis, J. Phys. Chem. A. 2005, 109, 8106
16. J. Clayden, L. Lemiègre, M. Helliwell, J. Org. Chem. 2007, 72, 2302
17. J. Clayden, L. Lemiègre, G. A. Morris, M. Pickworth, T. J. Snape, L. H. Jones, J. Am. Chem. Soc. 2008, 130, 15193
18. M. Kudo, T. Hanashima, A. Muranaka, H. Sato, M. Uchiyama, I. Azumaya, T. Hirano, H. Kagechika, A. Tanatani, J. Org. Chem. 2009, 74, 8154
19. J. Clayden, U. Hennecke, M. A. Vincent, I. H. Hillier, M. Helliwell, Phys. Chem. Chem. Phys. 2010, 12, 15056
20. C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5773
21. M. O. Senge, K. R. Gerzevske, G. H. Vicente, T. P. Forsyth, K. M. Smith, Angew. Chem., Int. Ed. Engl. 1993, 32, 750
22. A. Osuka, S. Nakajima, T. Nagata, K. Maruyama, K. Toriumi, Angew. Chem., Int. Ed. Engl. 1991, 30, 582
23. J. P. Fillers, K. G. Ravichandran, I. Abdalmuhdi, A. Tulinsky, C. K. Chang, J. Am. Chem. Soc. 1986, 108, 417
24. A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1988, 110, 4454
25. V. V. Borovkov, J. M. Lintuluoto, Y. Inoue, J. Phys. Chem. B. 1999, 103, 5151
26. J. T. Fletcher, M. J. Therien, J. Am. Chem. Soc. 2002, 124, 4298
27. S. Yagi, M. Ezoe, I. Yonekura, T. Takagishi, H. Nakazumi, J. Am. Chem. Soc. 2003, 125, 4068
28. V. V. Borovkov, J. Fujii, A. Muranaka, G. A. Hembury, T. Tanaka, A. Ceulemans, N. Kobayashi, Y. Inoue, Angew. Chem., Int. Ed. 2004, 43, 5481
29. J. P. Collman, A. O. Chong, G. B. Jameson, R. T. Oakley, E. Rose, E. R. Schmittou, J. A. Ibers, J. Am. Chem. Soc. 1981, 103, 516
30. M. Kasha, H. R. Rawls, M. A. El-Bayoumi, Pure Appl. Chem. 1965, 11, 371
31. M. O. Senge, M. G. H. Vicente, K. R. Gerzevske, T. P. Forsyth, K. M. Smith, Inorg. Chem. 1994, 33, 5625
32. H. Higuchi, M. Shinbo, M. Usuki, M. Takeuchi, Y. Hasegawa, K. Tani, J. Ojima, Bull. Chem. Soc. Jpn. 1999, 72, 1887