Computational study on a HS - sensing reaction utilizing a pyrylium derivative

Journal of Physical Chemistry A

Volumn 116, Issue 22, 2012, Pages 5420-5427

  Sheng, Yinghong ^a   Ren, Yi ^b  

^a FLORIDA GULF COAST UNIVERSITY   (United States)

^b SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION MAXIMA; ACIDIC CONDITIONS; COMPUTATIONAL STUDIES; GASPHASE; HYDRONIUM CATIONS; MOLECULAR ORBITAL THEORY; NEUTRAL CONDITIONS; PYRYLIUM; RED SHIFT; SENSING MECHANISM; THIOPYRYLIUM; UV-VIS ABSORPTIONS;

DOPPLER EFFECT; HYDROGEN SULFIDE; MOLECULAR ORBITALS;

SOLUTIONS;

COLORING AGENT; FUSED HETEROCYCLIC RINGS; HYDROGEN SULFIDE; PYRYLIUM 1; SOLVENT; THIOPHENE DERIVATIVE; THIOPYRYLIUM; WATER;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; GAS; PH; QUANTUM THEORY; THERMODYNAMICS;

ABSORPTION; COLORING AGENTS; COMPUTER SIMULATION; GASES; HETEROCYCLIC COMPOUNDS, 3-RING; HYDROGEN SULFIDE; HYDROGEN-ION CONCENTRATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; SOLVENTS; THERMODYNAMICS; THIOPHENES; WATER;

EID: 84861877348     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp300353y     Document Type: Article

References (84)

1. Silva, M. P. S. P.; da Silva, I. S.; Abate, G.; Masini, J. C. Talanta 2001, 53, 843-850
2. Tang, D.; Santshi, P. H. J. Chromatogr., A 2000, 883, 305-309
3. Spazoani, M. A.; Davis, J. L.; Tinani, M.; Carroll, M. K. Analyst 1997, 122, 1555-1557
4. Weiss, J.; Gobl, M. Fresenius' Z. Anal. Chem. 1985, 320, 439-444
5. Giuriati, C.; Cavalli, S.; Gorno, A.; Badacco, D.; Pastore, P. J. Chromatogr., A 2004, 1023, 105-112
6. Han, K.; Koch, W. F. Anal. Chim. 1987, 59, 1016
7. Wang, W.; Chen, Y.; Wu, M. Analyst 1984, 109, 281-286
8. Miura, Y.; Matsushita, Y.; Haddad, P. R. J. Chromatogr., A. 2005, 1085, 47-53
9. Divjak, B.; Goessler, W. J. Chromatogr., A 1999, 844, 161-169
10. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516
11. Gale, P. A. Coord. Chem. Rev. 2001, 213, 79-128
12. Amendola, V.; Fabbrizzi, L.; Mangano, C.; Pallavicini, P.; Poggi, A.; Taglietti, A. Coord. Chem. Rev. 2001, 219-221, 821-837
13. Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972
14. 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
15. Hayashita, T.; Honodera, T.; Kato, R.; Nishizawa, S.; Teramae, N. Chem. Commun. 2000, 755-756
16. Han, M. S.; Kim, D. H. Angew. Chem., Int. Ed. 2002, 41, 3809-3811
17. Jimenez, D.; Martinez-Mañez, R.; Sancenon, F.; Ros-Lis, J. V.; Benito, A.; Soto, J. J. Am. Chem. Soc. 2003, 125, 9000-9001
18. Zakrzewski, R.; Ciesielski, W.; Ulanowska, A.; Martinez-Mañez, R. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 1139-1148
19. Balaban, A. T.; Fischer, G. W.; Dinculescu, A.; Koblik, A. V.; Dorofeenko, G. N.; Mezheritskii, V. V.; Schroth, W. In Pyrylium Salts: Synthesis, Reactions and Physical Properties; Advances in Heterocyclic Chemistry, Supplement 2; Katrisky, A. R., Ed.; Academic Press: New York, 1982.
20. Balaban, T. S.; Balaban, A. T. In Science of Synthesis; Houben-Weyl Methods of Molecular Transformations; Thomas, D. E., Ed.; Georg Thieme Verlag: Stuttgart, Germany, Vol. 14, 2003; pp 11-200.
21. Bell, J. R.; Franken, A.; Garner, C. M. Tetrahedron 2009, 65, 9368-9372
22. Müller, C.; Vogt, D. C. R. Chimie 2010, 13, 1127-1143
23. Ba, F.; Poul, P. L.; Guen, R. L.; Cabon, N.; Caro, B. Tetrahedron Let. 2010, 51, 605-608
24. Sadhiya Banu, I.; Ramamurthy, P. J. Photochem. Photobiol., A 2009, 201, 175-182
25. Che, Y.; Ma, W.; Ji, H.; Zhao, J.; Ling, Z. J. Phys. Chem. B 2006, 110, 2942-2948
26. Latour, V.; Pigot, T.; Simon, M.; Cardy, H.; Lacombe, S. Photochem. Photobiol. Sci. 2005, 4, 221-229
27. Halder, M. Chem. Phys. 2004, 303, 243-253
28. Sanjuan, A.; Pillai, M. N.; Alvaro, M.; Garcia, H. Chem. Phys. Lett. 2001, 341, 153-160
29. Khairutdinov, R. F.; Hurst, J. K. J. Am. Chem. Soc. 2001, 123, 7352-7359
30. Miranda, M. A.; Garcia, H. Chem. Rev. 1994, 94, 1063-1089
31. Aprile, C.; Martin, R.; Alvaro, M.; Garcia, H.; Scaiano, J. C. Chem. Mater. 2009, 21, 884-890
32. Arques, A.; Amat, A. M.; Santos-Juanes, L.; Vercher, R. F.; Marín, M. L.; Miranda, M. A. Catal. Today 2009, 144, 106-111
33. Bayarri, B.; Carbonell, E.; Gimenez, J.; Esplugas, S.; Garcia, H. Chemosphere 2008, 72, 67-74
34. Bonesi, S. M.; Carbonell, E.; Garcia, H.; Fagnoni, M.; Albini, A. Appl. Catal., B 2008, 79, 368-375
35. Miranda, M. A.; Izquierdo, M. A.; Perez-Ruiz, R. J. Phys. Chem. A 2003, 107, 2478-2482
36. Haberl, U.; Steckhan, E.; Blechert, S.; Wiest, O. Chem.-Eur. J. 1999, 5, 2859-2865
37. Amat, A. M.; Arques, A.; Bossmann, S. H.; Braun, A. M.; Miranda, M. A.; Vercher, R. F. Catal. Today 2005, 101, 383-388
38. Amat, A. M.; Arques, A.; Bossmann, S. H.; Braun, A. M.; Goeb, S.; Miranda, M. A.; Oliveros, E. Chemosphere 2004, 57, 1123-1130
39. Alvaro, M.; Carbonell, E.; Fornes, V.; Garcia, H. New J. Chem. 2004, 28, 631-639
40. Chernova, R. K.; Yastrebova, N. I.; Ivanova, M. A. J. Anal. Chem. 2006, 61, 230-235
41. Martínez-Máñez, R.; Sancenón, F.; Soto, J. Chem. Commun. 2005, 2790-2792
42. Gómez-Valdemoro, A.; Martínez-Máñez, R.; Sancenón, F.; Garciá, F. C.; Garciá, J. M. Macromolecules 2010, 43, 7111-7121
43. Garcia-Acosta, B.; Comes, M.; Bricks, J. L.; Kudinova, M. A.; Kurdyukov, V. V.; Tolmachev, A. I.; Descalzo, A. B.; Marcos, M. D.; Martínez- Máñez, R.; Moreno, A.; Sancenón, F.; Soto, J.; Villaescusa, L. A.; Rurack, K.; Barat, J. M.; Escriche, I.; Amorós, P. Chem. Commun. 2006, 2239-2241
44. Comes, M.; Marcos, M. D.; Martínez-Máñez, R.; Sancenón, F.; Soto, J.; Villaescusa, L. A.; Amorós, P.; Beltran, D. Adv. Mater. 2004, 16, 1783-1786
45. Moghimi, A.; Maddah, B.; Yari, A.; Shamsipur, M.; Boostani, M.; Fall Rastegar, M.; Ghaderi, A. R. J. Mol. Struct. 2005, 752, 68-77
46. Moghimi, A.; Rsstegar, M. F.; Ghandi, M.; Taghizadeh, M.; Yari, A.; Shamsipur, M.; Yap, G. P. A.; Rahbarnoohi, H. J. Org. Chem. 2002, 67, 2065-2074
47. Rudat, B.; Birtalan, E.; Thomé, I.; Kölmel, D. K.; Horhoiu, V. L.; Wissert, M. D.; Lemmer, U.; Eisler, H.-J.; Balaban, T. S.; Bräse, S. J. Phys. Chem. B 2010, 114, 13473-13480
48. Sancenón, F.; Descalzo, A. B.; Martínez-Máñez, R.; Miranda, M. A.; Soto, J. Angew. Chem., Int. Ed. 2001, 40, 2640-2643
49. Wetzl, B. K.; Yarmoluk, S. M.; Craig, D. B.; Wolfbeis, O. S. Angew. Chem., Int. Ed. 2004, 43, 5400-5402
50. Yari, A.; Abdoli, H. A. J. Hazard. Mater. 2010, 178, 713-717
51. Polyzos, I.; Tsigaridas, G.; Fakis, M.; Giannetas, V.; Persephonis, P.; Mikroyannidis, J. J. Phys. Chem. B 2006, 110, 2593-2597
52. Polyzos, I.; Tsigaridas, G.; Fakis, M.; Giannetas, V.; Persephonis, P. Opt. Lett. 2005, 30, 2654-2656
53. Fakis, M.; Tsigaridas, G.; Polyzos, I.; Giannetas, V.; Persephonis, P.; Spiliopoulos, I.; Mikroyannidis, J. Chem. Phys. Lett. 2001, 342, 155-161
54. Zhou, Y.-F.; Feng, S.-Y. ChemPhysChem 2002, 3, 969-972
55. Alvaro, M.; Aprile, C.; Benitez, M.; Bourdelande, J. L.; Garcia, H.; Herance, J. R. Chem. Phys. Lett. 2005, 414, 66-70
56. Purvinis, G.; Priambodo, P. S.; Pomerantz, M.; Zhou, M.; Maldonado, T. A.; Magnusson, R. Opt. Lett. 2004, 29, 1108-1110
57. Nakayama, H.; Sugihara, O.; Okamoto, N.; Sate, H.; Mizuno, A.; Matsushima, R. J. Opt. Soc. Am. B 1998, 15, 477-483
58. Dave, K.; Ilies, M. A.; Scozzafava, A.; Temperini, C.; Vullo, D.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2011, 21, 2764-2768
59. Güzel, Ö.; Maresca, A.; Scozzafava, A.; Salman, A.; Balaban, A. T.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2009, 19, 2931-2934
60. Gong, W.-T.; Li, X.-C.; Ning, G.-L.; Zhu, L.; Wang, L.; Lin, Y. Spectrochim. Acta, Part A 2005, 62, 835-839
61. Kovacic, P. Curr. Med. Chem.: Anti-Cancer Agents 2005, 5, 501-506
62. Bauschlicher, C. W. Chem. Phys. Lett. 1995, 246, 40-44
63. El-Azhary, A. A.; Suter, H. U. J. Phys. Chem. 1996, 100, 15056-15063
64. Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785-789
65. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
66. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. J. Chem. Phys. 1989, 90, 5622-5629
67. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
68. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218
69. Sheng, Y.; Leszczynski, J.; Garcia, A.; Rosario, R.; Gust, D.; Springer, J. J. Phys. Chem. B 2004, 108, 16233-16243
70. Holmén, A.; Broo, A. Int. J. Quantum Chem. 1995, 22, 113-122
71. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 16, 217-219
72. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
73. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001
74. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681
75. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454-464
76. Straman, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224
77. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
78. Sheng, Y.; Leszczynski, J.; Nguyen, T.-Q.; Bamgbelu, A. Struct. Chem. 2007, 18, 827-832
79. Manoj, N.; Ajayakumar, G.; Gopidas, K. R.; Suresh, C. H. J. Phys. Chem. A 2006, 110, 11338-11345
80. Manoj, N.; Gopidas, K. R. J. Photochem. Photobiol., A 1999, 127, 31-37
81. Manoj, N.; Ajit Kumar, R.; Gopidas, K. R. J. Photochem. Photobiol., A 1997, 109, 109-118
82. Rulliére, C.; Declemy, A.; Balaban, A. T. Can J. Phys. 1985, 63, 191
83. Jha, P. C.; Luo, Y.; Polyzos, I.; Persephonis, P.; Ågren, H. J. Chem. Phys. 2009, 130, 174312/1-174312/7
84. Polyzos, I.; Tsigaridas, G.; Fakis, M.; Giannetas, V.; Persephonis, P.; Mikroyannidis, J. Chem. Phys. Lett. 2003, 369, 264-268