DFT calculation on 76 polybromophenazines: Their thermodynamic function and stability

Journal of Chemical and Engineering Data

Volumn 54, Issue 9, 2009, Pages 2404-2410

  Sun, Ping ^a   Yang, Guo Y ^a   Liu, Hong X ^a   Wang, Zun Y ^a  

^a JIAXING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; BROMINE ATOMS; CONSTANT PRESSURES; DFT CALCULATION; FORMATION HEAT; GASEOUS STATE; GAUSSIANS; ISODESMIC REACTIONS; MOLAR HEAT CAPACITIES; RELATIVE STABILITIES; STANDARD GIBBS ENERGY; THERMODYNAMIC FUNCTIONS; THERMODYNAMIC PARAMETER;

BROMINE; DENSITY FUNCTIONAL THEORY; GIBBS FREE ENERGY; SPONTANEOUS EMISSION; THERMODYNAMICS;

THERMODYNAMIC STABILITY;

EID: 70349542623     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je8008304     Document Type: Article

References (14)

1. Bolton, R. Rodd's chemistry of carbon compounds; Sainsbury, M., Ed.; Elsevier: Amsterdam, 2000; Vol.4, p 162, Part I J.
2. Turner, J. M.; Messenger, A. J. Occurrence, biochemistry, and physiology of phenazine pigment production. Adv. Microbial Physiol. 1986, 27, 211-275.
3. McDonald, M.; Mavrodi, D. V.; Thomashow, L. S.; Floss, H. G. Phenazine biosynthesis in Pseudomonas fluorescens: Branchpoint from the primary shikimate biosynthetic pathway and role of phenazine-1, 6-dicarboxylic acid. J. Am. Chem. Soc. 2001, 123 (38), 9459-9460.
4. de Andrade-Neto, V. F.; Goulart, M. O. F.; da Silva, J. F.; da Silva, M. J.; Pinto, M. Do C. F. R.; Pinto, A. V.; Zalis, M. G.; Carvalho, L. H.; Krettli, A. U. Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Bioorg. Med. Chem. Lett. 2004, 14, 1145-1149.
5. Wang, W.; Préville, P.; Morin, N.; Mounir, S.; Cai, W.; Arshad, S. M. Epatitis C viral IRES inhibition by phenazine and phenazine-like molecules. Bioorg. Med. Chem. Lett. 2000, 10 (11), 1151-1154.
6. Spicer, J. A.; Gamage, S. A.; Rewcastle, G. W.; Finlay, G. J.; Bridewell, D. J. A.; Baguley, B. C.; Denny, W. A. Bis (phenazine-1-carboxamides): Structure-activity relationships for a new class of dual topoisomerase I/II-directed anticancer drugs. J. Med. Chem. 2000, 43 (7), 1350-1357.
7. Cross, B.; Dunn, C. L.; Payne, D. H.; Tipton, J. D. Synthesis and pesticidal activity of phenazines. J. Sci. Food Agric. 1969, 20, 340-344.
8. Cerecetto, H.; González, M.; Lavaggi, M. L.; Azqueta, A.; López de Cerain, A.; Monge, A. Phenazine 5, 10-dioxide derivatives as hypoxic selective cytotoxins. J. Med. Chem. 2005, 48 (1), 21-23.
9. Ashraf, M. A.; John, F. G.; Rajinder, S. N. Formation of bromodioxin analogs from closed tube pyrolysis of 2, 4, 6-tribromoaniline (I). Chemosphere 1988, 17 (12), 2391-2396.
10. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; 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.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03 (Revision A.1), Gaussian, Inc.: Pittsburgh, PA, 2003.
11. Yao, Y. B.; Xie, T.; Gao, Y. M. Handbook of Physics and Chemistry, 1st ed.; Shanghai Science and Technology Press: Shanghai, 1985; pp 912-1015.
12. Qiu, J.; Liu, H.; Wang, Z. Y.; Wang, L. S.; Yu, H. X. DFT Study on the Thermodynamic Properties of Polychloridized Phenoxazines. Acta Chin. Sinica 2008, 66 (24), 2659-2668.
13. Dean, J. A. Lange's Handbook of Chemistry, 13th ed.; McGraw-Hill: New York, 1991.
14. Wang, Z. Y; Zhai, Z. C.; Wang, L. S.; Chen, J. L.; Kikuchi, O.; Watanabe, T. Prediction of gas phase thermodynamic function of polychlorinated dibenzo-p-dioxins using DFT. J. Mol. Struct. (THEOCHEM) 2004, 672 (1-3), 97-104.