A new chromo-chemodosimeter selective for sulfide anion

Journal of the American Chemical Society

Volumn 125, Issue 30, 2003, Pages 9000-9001

  Jiménez, Diego ^a   Martínez Máñez, Ramón ^a   Sancenón, Félix ^a   Ros Lis, José V ^a   Benito, A ^a   Soto, Juan ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,4,6 TRIPHENYLPYRYLIUM DERIVATIVE; ACETONITRILE; ANILINE DERIVATIVE; CHROMOGENIC SUBSTRATE; HYDROGEN SULFIDE; PYRIDINIUM DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOPHORE; CHROMO CHEMODOSIMETER; COLORIMETRY; COVALENT BOND; CYCLIZATION; DOSIMETRY;

EID: 0042805257     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0347336     Document Type: Article

References (29)

1. Hydrogen Sulfide; Geneva, World Health Organization, 1981 (Environmental Health Criteria, No. 19).
2. (a) Gosselin, R. E.; Smith, R. P.; Hodge, H. C. Hydrogen Sulfide. In Clinical Toxicology of Commercial Products, 5th ed.; Williams and Wilkins: Baltimore, MD, 1984; pp III-198-III-202.
3. (b) Patwardhan, S. A.; Abhyankar, S. M. Toxic and Hazardous Gases. IV. Colourage 1988, 35, 15-18.
4. (a) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516,
5. (b) Gale, P. A. Coord. Chem. Rev. 2001, 213, 79-128.
6. (c) Amendola, V.; Fabbrizzi, L.; Mangano, C.; Pallavicini, P.; Poggi, A.; Taglietti, A. Coord. Chem. Rev. 2001, 219-221, 821-837.
7. (d) Wiskur, S. L.; Aït-Haddou, H.; Lavigne, J. J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972.
8. (a) Amendola, V.; Bastianello, E.; Fabbrizzi, L.; Mangano, C.; Pallavicini, P.; Perotti, A.; Manotti-Lanfredi, A.; Ugozzoli, F. Angew. Chem., Int. Ed. 2000, 39, 2917-2920.
9. (b) Hayashita, T.; Honodera, T.; Kato, R.; Nishizawa, S.; Teramae, N. Chem. Commun. 2000, 755-756.
10. (c) Han, M. S.; Kim, D. H. Angew. Chem., Int. Ed. 2002, 41, 3809-3811.
11. (a) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438-10439.
12. (b) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777-1780.
13. (c) Lee, D. H.; Lee, H. Y.; Lee, K. H.; Hong, J.-I. Chem. Commun. 2001, 1188-1189.
14. (d) Piatek, P.; Jurczak, J. Chem. Commun. 2002, 2450-2451.
15. (a) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649-652.
16. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
17. (c) Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666-3669.
18. (d) Wiskur, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2001, 123, 10109-10110.
19. (e) Aït-Haddou, H.; Wiskur, S. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2001, 123, 11296-11297.
20. (a) Mohr, G. J. Chem. Commun. 2002, 2646-2647.
21. (b) Dujols, V.; Ford, F.; Czarnik, A. W. J. Am. Chem. Soc. 1997, 119, 7386-7387.
22. (c) Sancenón, F.; Descalzo, A. B.; Martínez-Máñez, R.; Miranda, M. A.; Soto, J. Angew. Chem., Int. Ed. 2001, 40, 2640-2643.
23. (d) Ros-Lis, J. V.; Martínez-Máñez, R.; Soto, J. Chem. Commun. 2002, 2248-2249.
24. (e) Sancenón, F.; Martínez-Máñez, R.; Miranda, M. A.; Seguí, M. J.; Soto, J. Angew. Chem., Int. Ed. 2003, 42, 647-650.
25. 1 is straightforward by reaction of 2,6-diphenylpyrylium perchlorate with N,N-dimethylaniline in DMF at 150 °C. Subsequent addition to the reaction crude of diethyl ether afforded the desidered compound in 53% yield as a red-magenta solid.
26. Staunton, J. Compr. Org. Chem. 1979, 4, 607-627.
27. Miranda, M. A.; García, H. Chem. Rev. 1994, 94, 1063-1089.
28. Compound III was prepared by following the experimental procedure described in J. Org. Chem. 2002, 67, 2065-2074.
29. 1 might be used as chromogenic reagent for the determination of moderate amounts of cyanide and primary aliphatic amines (the color change from magenta to yellow is observed in the presence of ca. 100 equiv) in water:acetonitrile mixtures.