Theoretical study of structure, energetic, hydrogen bonds strength and intramolecular proton transfer of 2-(2-R (R=OH, NH2, SH) phenyl (or Pyridyl)) benzoxazoles (or Benzothiazoles)

Chinese Journal of Chemistry

Volumn 29, Issue 4, 2011, Pages 650-654

  Yi, Pinggui ^a   Peng, Hongliang ^a   Wang, Zhaoxu ^a   Yu, Xianyong ^a   Li, Xiaofang ^a   Liang, Yonghong ^a  

^a HUNAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

benzothiazole; benzoxazole; density functional calculations; hydrogen bonds; intramolecular proton transfer

Indexed keywords

EID: 79955533348     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201190136     Document Type: Article

References (32)

1. Catalán, J.,;, Fabero, F.,;, Guifarro, M. S.,;, Claramunt, R. M.,;, Santa-Maria, M. D.,;, Foces-Foces, M. C.,;, Cano, F. H.,;, Elguero, J.,;, Sastre, R.,. J. Am. Chem. Soc., 1990, 112, 747.
2. Nishyiya, T.,;, Yamuchi, S.,;, Hirota, N.,;, Baba, M.,;, Hamazaki, I.,. J. Phys. Chem., 1986, 90, 5730.
3. Sytnik, A.,;, Kasha, M.,. Proc. Nat. Acad. Sci. U. S. A., 1994, 91, 8627.
4. Kraus, G. A.,;, Zhang, W.,;, Fehr, M. J.,;, Petrich, J. W.,;, Wannemehler, Y.,;, Carpenter, S.,. Chem. Rev., 1996, 96, 523.
5. Sobolewski, A. L.,;, Domcke, W.,. J. Phys. Chem. A, 2007, 111, 46.
6. Steiner, T.,. Angew. Chem., Int. Ed., 2002, 41, 48.
7. Cleland, W. W.,. Biochemistry, 1992, 31, 317.
8. Cleland, W. W.,;, Krreevoy, M. M.,. Science, 1994, 264, 1887.
9. Frey, P. A.,;, Whitt, S. A.,;, Tobin, J. B., Science, 1994, 264, 1927.
10. Scheiner, S.,. J. Mol. Struct. (THEOCHEM), 1994, 307, 65.
11. Sadhukhan, S.,;, Muñoz, D.,;, Adamo, C.,;, Scuseria, G. E.,. Chem. Phys. Lett., 1999, 306, 83.
12. Kijak, M.,;, Nosenko, Y.,;, Singh, A.,;, Thummel, R. P.,;, Waluk, J.,. J. Am. Chem. Soc., 2007, 129, 2738.
13. Catalán, J.,;, Palomar, J.,;, de Paz, J. L. G.,. J. Phys. Chem. A, 1997, 101, 7914.
14. Chou, P. T.,;, Martinez, M. L.,;, Studer, S. L.,. Chem. Phys. Lett., 1992, 195, 586.
15. Dupradeau, F. Y.,;, Case, D. A.,;, Yu, C.,;, Jimenez, R.,;, Romesberg, F. E.,. J. Am. Chem. Soc., 2005, 127, 15612.
16. Vá zquez, S. R.,;, Rodríguez, M. C.,;, Mosquera, M.,;, Rodríguez-Prieto, F.,. J. Phys. Chem. A, 2007, 111, 1814.
17. Becke, A. D.,. J. Chem. Phys., 1993, 98, 5648.
18. Reed, A. E.,;, Curtiss, L. A.,;, Weinhold, F.,. Chem. Rev., 1988, 88, 899.
19. Hass, K. C.,;, Schneider, W. F.,;, Estévez, C. M.,;, Bach, R. D.,. Chem. Phys. Lett., 1996, 263, 414.
20. Foresman, J. B.,;, Head-Gordon, M.,;, Pople, J. A.,;, Frisch, M. J.,. J. Phys. Chem., 1992, 96, 135.
21. 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.,;, Millam, J. M.,;, Iyengar, S. S.,;, Tomasi, J.,;, Barone, V.,;, Mennucci, B.,;, Cossi, M.,;, Scalmani, G.,;, Rega, N.,;, Petersson, G. A.,;, Nakatsuji, H.,;, Hada, M.,;, Ehara, M.,;, Toyota, K.,;, Fukuda, R.,;, Hasegawa, J.,;, Ishida, M.,;, Nakajima, T.,;, Honda, Y.,;, Kitao, O.,;, Nakai, H.,;, Klene, M.,;, Li, X.,;, Knox, J. E.,;, Hratchian, H. P.,;, Cross, J. B.,;, Bakken, V.,;, Adamo, C.,;, Jaramillo, J.,;, Gomperts, R.,;, Stratmann, R. E.,;, Yazyev, O.,;, Austin, A. J.,;, Cammi, R.,;, Pomelli, C.,;, Ochterski, J. W.,;, Ayala, P. Y.,;, Morokuma, K.,;, Voth, G. A.,;, Salvador, P.,;, Dannenberg, J. J.,;, Zakrzewski, V. G.,;, Dapprich, S.,;, Daniels, A. D.,;, Strain, M. C.,;, Farkas, O.,;, Malick, D. K.,;, Rabuck, A. D.,;, Raghavachari, K.,;, Foresman, J. B.,;, Ortiz, J. V.,;, Cui, Q.,;, Baboul, A. G.,;, Clifford, S.,;, Cioslowski, J.,;, Stefanov, B. B.,;, Liu, G.,;, Liashenko, A.,;, Piskorz, P.,;, Komaromi, I.,;, Martin, R. L.,;, Fox, D. J.,;, Keith, T.,;, Al-Laham, M. A.,;, Peng, C. Y.,;, Nanayakkara, A.,;, Challacombe, M.,;, Gill, P. M. W.,;, Johnson, B.,;, Chen, W.,;, Wong, M. W.,;, Gonzalez, C.,;, Pople, J. A., Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh, PA, 2003.
22. Lampert, H.,;, Mikenda, W.,;, Karpfen, A.,. J. Phys. Chem., 1997, 100, 22254.
23. Nosenko, Y.,;, Wiosna-Sa?yga, G.,;, Kunitski, M.,;, Petkova, I.,;, Singh, A.,;, Buma, W. J.,;, Thummel, R. P.,;, Brutschy, B.,;, Waluk, J.,. Angew. Chem., Int. Ed., 2008, 47, 1.
24. Xi, Y., M.S. Thesis, Northwestern University, Xian, 2006 (in Chinese).
25. Yi, P. G.,;, Peng, H. L.,;, Yu, X. Y.,;, Wang, Z. X,;, Tang, Z. Q.,;, Wang, T.,. Acta Chim. Sinica, 2009, 67, 276 (in Chinese).
26. Yi, P. G.,;, Liang, Y. H.,;, Cao, C. Z.,. Chem. Phys., 2005, 315, 297.
27. Etter, M. C.,. Acc. Chem. Res., 1990, 23, 120.
28. Abraham, M. H., Chem. Soc. Rev., 1993, 22, 73.
29. Kar, T.,;, Scheiner, S.,;, Čuma, M.,. J. Chem. Phys., 1999, 111, 849.
30. Sobolewski, A. L.,;, Domcke, W.,. Phys. Chem. Chem. Phys., 1999, 1, 3065.
31. Liang, Y. H.,;, Yi, P. G.,. Chem. Phys. Lett., 2007, 438, 173.
32. Liang, Y. H.,;, Yi, P. G.,;, Peng, H. L.,. Chem. Phys. Lett., 2008, 466, 6.