Substituent effects on the solvatochromism of 2-phenylimidazopyrazinones: Effective control of the color variation range and sensitivity toward an indication of the proton-donor ability of solvents by an electron-withdrawing group substitution

Chemistry Letters

Volumn 33, Issue 11, 2004, Pages 1484-1485

  Takamuki, Yoshiharu ^a   Maki, Shojiro ^a   Niwa, Haruki ^a   Ikeda, Hiroshi ^b   Hirano, Takashi ^a  

^a UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLIMIDAZOPYRAZINONE; PHENYL GROUP; PROTON; SOLVENT; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; COLOR; ELECTRON; SENSITIVITY ANALYSIS; SOLVATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 13544266450     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1484     Document Type: Article

References (20)

1. Reviews of bioluminescence: a) T. Goto, Pure Appl. Chem., 17, 421 (1968). b) Y. Ohmiya and T. Hirano, Chem. Biol., 3, 337 (1996).
2. Reviews of bioluminescence: a) T. Goto, Pure Appl. Chem., 17, 421 (1968). b) Y. Ohmiya and T. Hirano, Chem. Biol., 3, 337 (1996).
3. Examples of chemiluminescence study: a) R. Saito, T. Hirano, H. Niwa, and M. Ohashi, Chem. Lett., 1998, 1711. b) T. Hirano, R. Negishi, M. Yamaguchi, F. Q. Chen, Y. Ohmiya, F. I. Tsuji, and M. Ohashi, Tetrahedron, 53, 12903 (1997). c) T. Hirano, Y. Gomi, T. Takahashi, K. Kitahara, F. Q. Chen, I. Mizoguchi, S. Kyushin, and M. Ohashi, Tetrahedron Lett., 39, 5771 (1992).
4. Examples of chemiluminescence study: a) R. Saito, T. Hirano, H. Niwa, and M. Ohashi, Chem. Lett., 1998, 1711. b) T. Hirano, R. Negishi, M. Yamaguchi, F. Q. Chen, Y. Ohmiya, F. I. Tsuji, and M. Ohashi, Tetrahedron, 53, 12903 (1997). c) T. Hirano, Y. Gomi, T. Takahashi, K. Kitahara, F. Q. Chen, I. Mizoguchi, S. Kyushin, and M. Ohashi, Tetrahedron Lett., 39, 5771 (1992).
5. Examples of chemiluminescence study: a) R. Saito, T. Hirano, H. Niwa, and M. Ohashi, Chem. Lett., 1998, 1711. b) T. Hirano, R. Negishi, M. Yamaguchi, F. Q. Chen, Y. Ohmiya, F. I. Tsuji, and M. Ohashi, Tetrahedron, 53, 12903 (1997). c) T. Hirano, Y. Gomi, T. Takahashi, K. Kitahara, F. Q. Chen, I. Mizoguchi, S. Kyushin, and M. Ohashi, Tetrahedron Lett., 39, 5771 (1992).
6. S. Nakai, M. Yasui, M. Nakazato, F. Iwasaki, S. Maki, H. Niwa, M. Ohashi, and T. Hirano, Bull. Chem. Soc. Jpn., 76, 2361 (2003).
7. +, 81), 94 (100).
8. A. Arrault, M. Dubuisson, S. Gharbi, U. Marchand, T. Verbeuren, A. Rupin, A. Cordi, E. Bouskela, J. F. Rees, and J. Marchand-Brynaert, Bioorg. Med. Chem. Lett., 13, 653 (2003).
9. The UV-vis absorption spectrum of la in acetic acid showed a weak absorption band around 570 nm and the solution looked dark orange. This behavior may be due to a partial protonation at the dimethylamino group.
10. a) R. W. Taft and M. J. Kamlet, J. Am. Chem. Soc., 98, 2886 (1976).
11. b) M. J. Kamlet and R. W. Taft, J. Am. Chem. Soc., 98, 377 (1976).
12. c) M. J. Kamlet, J.-L. M. Abboud, and R. W. Taft, J. Am. Chem. Soc., 99, 6027 (1977).
13. d) M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham, and R. W. Taft, J. Org. Chem., 48, 2877 (1983).
14. C. Reichardt, "Solvents and Solvent Effects in Organic Chemistry," 2nd ed., VCH, Weinheim (1990).
15. a) M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).
16. b) J. J. P. Stewart, J. Comput. Chem., 10, 209 (1989).
17. c) A. Klant and G. Shuurmann, J. Chem. Soc., Perkin Trans. 2, 1993, 799.
18. MOPAC2002 ver. 1.0, Fujitsu Ltd., Tokyo, Japan (2001); J. J. P. Stewart, Int. J. Quantum. Chem., 58, 133 (1996).
19. MOPAC2002 ver. 1.0, Fujitsu Ltd., Tokyo, Japan (2001); J. J. P. Stewart, Int. J. Quantum. Chem., 58, 133 (1996).
20. + has a proton at the O10. AM1-COSMO calculations showed that the O10 atoms of 1a-1e are the most negatively charged (net atomic charge = ca. -0.6) among all the atoms, supporting that the O10 atoms are the key participants for the hydrogen-bonding interactions with solvent molecules.