A DFT study on the electron affinity of tetrachloro-p-benzoquinone: Toward to understanding its electron-accepting ability in solution

Computational and Theoretical Chemistry

Volumn 1006, Issue , 2013, Pages 127-132

  Li, Ping ^a,b   Wang, Wei Hua ^b   Sun, Hai Tao ^b   Bi, Si Wei ^b  

^a SHANDONG UNIVERSITY   (China)

^b QUFU NORMAL UNIVERSITY   (China)

Author keywords

Density functional theory (DFT); Electron affinity; Tetrachloro p benzoquinone

Indexed keywords

EID: 84872675838     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2012.11.022     Document Type: Article

References (54)

1. Zhu B.Z., Zhu J.G., Mao L., Kalyanaraman B., Shan G.Q. Detoxifying carcinogenic polyhalogenated quinones by hydroxamic acids via an unusual double Lossen rearrangement mechanism. Proc. Natl. Acad. Sci. USA 2010, 107:20686-20690.
2. Bolton J.L., Trush M.A., Penning T.M., Dryhurst G., Monks T.J. Role of quinones in toxicology. Chem. Res. Toxicol. 2000, 13:135-160.
3. Horke D.A., Verlet J.R.R. Time-resolved photoelectron imaging of the chloranil radical anion: ultrafast relaxation of electronically excited electron acceptor states. Phys. Chem. Chem. Phys. 2011, 13:19546-19552.
4. Zhu B.Z., Shan G.Q. Potential mechanism for pentachlorophenol-induced carcinogenicity: a novel mechanism for metal-independent production of hydroxyl radicals. Chem. Res. Toxicol. 2009, 22:969-977.
5. Meunier B. Catalytic degradation of chlorinated phenols. Science 2002, 296:270-271.
6. Gupta S.S., Stadler M., Noser C.A., Ghosh A., Steinhoff B., Lenoir D., Horwitz C.P., Schramm K., Collins T.J. Rapid total destruction of chlorophenols by activated hydrogen peroxide. Science 2002, 296:326-328.
7. Sarr D.H., Kazunga C., Charles M.J., Pavlovich J.G., Aitken M.D. Decomposition of tetrachloro-1,4-benzoquinone (p-chloranil) in aqueous solution. Environ. Sci. Technol. 1995, 29:2735-2740.
8. Waidyanatha S., McDonald T.A., Lin P.H., Rappaport S.M. Measurement of hemoglobin and albumin adducts of tetrachlorobenzoquinone. Chem. Res. Toxicol. 1994, 7:463-468.
9. Ranzieri P., Masino M., Girlando A. Charge-sensitive vibrations in p-chloranil: the strange case of the CC antisymmetric stretching. J. Phys. Chem. B 2007, 111:12844-12848.
10. Katan C., Blöchl P.E., Margl P., Koenig C. First-principles molecular-dynamics simulations for neutral p-chloranil and its radical anion. Phys. Rev. B 1996, 53:12112-12120.
11. Boesch S.E., Wheeler R.A. Π -Donor substituent effects on calculated structures, spin properties, and vibrations of radical anions of p-chloranil, p-fluoranil, and p-benzoquinone. J. Phys. Chem. A 1997, 101:8351-8359.
12. Boesch S.E., Wheeler R.A. Π -Donor substituent effects on calculated structures and vibrational frequencies of p-benzoquinone, p-fluoranil, and p-chloranil. J. Phys. Chem. 1995, 99:8125-8134.
13. Girlando A., Zanon I., Bozio R., Pecile C. Raman and infrared frequency shifts proceeding from ionization of perhalo-p-benzoquinones to radical anions. J. Chem. Phys. 1978, 68:22-31.
14. Zhu B.Z., Fan R.M., Qu N. A novel mechanism for metal-independent hydroxyl radical production by hydrogen peroxide and halogenated quinines. Mini-Rev. Org. Chem. 2011, 8:434-437.
15. Zhu B.Z., Shan G.Q., Huang C.H., Kalyanaraman B., Mao L., Du Y.G. Metal-independent decomposition of hydroperoxides by halogenated quinones: detection and identification of a quinone ketoxy radical. Proc. Natl. Acad. Sci. USA 2009, 106:11466-11471.
16. Zhu B.Z., Kalyanaraman B., Jiang G.B. Molecular mechanism for metal-independent production of hydroxyl radicals by hydrogen peroxide and halogenated quinones. Proc. Natl. Acad. Sci. USA 2007, 104:17575-17578.
17. Zhu B.Z., Zhao H.T., Kalyanaraman B., Liu J., Shan G.Q., Du Y.G., Frei B. Mechanism of metal-independent decomposition of organic hydroperoxides and formation of alkoxyl radicals by halogenated quinones. Proc. Natl. Acad. Sci. USA 2007, 104:3698-3702.
18. Rahimipour S., Gescheidt G., Bilkis I., Fridkin M., Weiner L. Towards the efficiency of pharmacologically active quinoid compounds: electron transfer and formation of reactive oxygen species. Appl. Magn. Reson. 2010, 37:629-648.
19. Periquet V., Moreau A., Carles S., Schermann J.P., Desfrancüois C. Cluster size effects upon anion solvation of N-heterocyclic molecules and nucleic acid bases. J. Electron Spectrosc. Relat. Phenom. 2000, 106:141-151.
20. Chen E.S.D., Chen E.C.M., Sane N., Shulze S. Classification of organic molecules to obtain electron affinities from half-wave reduction potentials: cytosine, uracil, thymine, guanine and adenine. Bioelectrochem. Bioenergetics 1999, 48:69-78.
21. Kebarle P., Chowdhury S. Electron affinities and electron-transfer reactions. Chem. Rev. 1987, 87:513-534.
22. Heinis T., Chowdhury S., Scott S.L., Kebarle P. Electron affinities of benzo-, naphtho-, and anthraquinones determined from gas-phase equilibria measurements. J. Am. Chem. Soc. 1988, 110:400-407.
23. Cooper C.D., Frey W.F., Compton R.N. Negative ion properties of fluoranil, chloranil, and bromanil: electron affinities. J. Chem. Phys. 1978, 69:2367-2374.
24. Zhang Q.Z., Yu W.N., Zhang R.X., Zhou Q., Gao R., Wang W.X. Quantum chemical and kinetic study on dioxin formation from the 2,4,6-TCP and 2,4-DCP precursors. Environ. Sci. Technol. 2010, 44:3395-3403.
25. Xu F., Yu W.N., Zhou Q., Gao R., Sun X.Y., Zhang Q.Z., Wang W.X. Mechanism and direct kinetic study of the polychlorinated dibenzo-p-dioxin and dibenzofuran formations from the radical/radical cross-condensation of 2,4-dichlorophenoxy with 2-chlorophenoxy and 2,4,6-trichlorophenoxy. Environ. Sci. Technol. 2011, 45:643-650.
26. Qu X.H., Wang H., Zhang Q.Z., Shi X.Y., Xu F., Wang W.X. Mechanistic and kinetic studies on the homogeneous gas-phase formation of PCDD/Fs from 2,4,5-trichlorophenol. Environ. Sci. Technol. 2009, 43:4068-4075.
27. Altarawneh M., Dlugogorski B.Z., Kennedy E.M., Mackie J.C. Theoretical study of reaction pathways of dibenzofuran and dibenzo-p-dioxin under reducing conditions. J. Phys. Chem. A 2007, 111:7133-7140.
28. Betowski L.D., Enlow M., Riddick L., Aue D.H. Calculation of electron affinities of polycyclic aromatic hydrocarbons and solvation energies of their radical anion. J. Phys. Chem. A 2006, 110:12927-12946.
29. Zhang Q.Z., Li S.Q., Qu X.H., Shi X.Y., Wang W.X. A quantum mechanical study on the formation of PCDD/Fs from 2-chlorophenol as precursor. Environ. Sci. Technol. 2008, 42:7301-7308.
30. Arulmozhiraja S., Morita M. Electron affinities and reductive dechlorination of toxic polychlorinated dibenzofurans: a density functional theory Study. J. Phys. Chem. A 2004, 108:3499-3508.
31. Zhang Q.Z., Qu X.H., Wang H., Xu F., Shi X.Y., Wang W.X. Mechanism and thermal rate constants for the complete series reactions of chlorophenols with H. Environ. Sci. Technol. 2009, 43:4105-4112.
32. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98:5648-5652.
33. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37:785-789.
34. Rienstra-Kiracofe J.C., Tschumper G.S., Schaefer H.F., Nandi S., Ellison G.B. Atomic and molecular electron affinities: photoelectron experiments and theoretical computations. Chem. Rev. 2002, 102:231-282.
35. Zhao Y.Y., Tao F.M., Zeng E.Y. Structures, reductive dechlorination, and electron affinities of selected polychlorinated dibenzo-p-dioxins: density functional theory study. J. Phys. Chem. A 2007, 111:11638-11644.
36. Melicherčík M., PaŠteka L.F., Neogrády P., Urban M. Electron affinities of uracil: microsolvation effects and polarizable continuum model. J. Phys. Chem. A 2012, 116:2343-2351.
37. Gupta A., Jaeger H.M., Compaan K.R., Schaefer H.F. Electron attachment to the guanine-cytosine nucleic acid base pair and the effects of monohydration and proton transfer. J. Phys. Chem. B 2012, 116:5579-5587.
38. Wang L.M., Tang A.L. Atmospheric oxidation mechanisms of polychlorinated dibenzo-p-dioxins are different from those of benzene and dibenzofuran: a theoretical prediction. Chemosphere 2011, 82:782-785.
39. Wang X.B., Fu Q., Yang J.L. Electron affinities and electronic structures of o-, m-, and p-hydroxyphenoxyl radicals: a combined low-temperature photoelectron spectroscopic and ab initio calculation study. J. Phys. Chem. A 2010, 114:9083-9089.
40. Hasegawa J., Ishida M., Nakatsuji H., Lu Z., Liu H., Yang W. Energetics of the electron transfer from bacteriopheophytin to ubiquinone in the photosynthetic reaction center of rhodopseudomonas viridis: theoretical Study. J. Phys. Chem. B 2003, 107:838-847.
41. O'Malley P.J. A density functional study of the effect of reduction on the geometry and electron affinity of hydrogen bonded 1,4-benzoquinone. Implications for quinone reduction and protonation in photosynthetic reaction centres. Chem. Phys. Lett. 1997, 274:251-254.
42. Grafton A.K., Wheeler R.A. A comparison of the properties of various fused-ring quinones and their radical anions using Hartree-Fock and hybrid Hartree-Fock/density functional methods. J. Phys. Chem. A 1997, 101:7154-7166.
43. Boesch S.E., Grafton A.K., Wheeler R.A. Electron affinities of substituted p-benzoquinones from hybrid Hartree-Fock/density-functional calculations. J. Phys. Chem. 1996, 100:10083-10087.
44. Bader R.F.W. Atoms in Molecules: A Quantum Theory 1990, Oxford University Press, Oxford, UK.
45. Pacios L.F. Topological descriptors of the electron density and the electron localization function in hydrogen bond dimers at short intermonomer distances. J. Phys. Chem. A 2004, 108:1177-1188.
46. Jenkins S., Morrison I. The chemical character of the intermolecular bonds of seven phases of ice as revealed by ab initio calculation of electron densities. Chem. Phys. Lett. 2000, 317:97-102.
47. Arnold W.D., Oldfield E. The chemical nature of hydrogen bonding in proteins via NMR: J-couplings, chemical shifts, and AIM theory. J. Am. Chem. Soc. 2000, 122:12835-12841.
48. Rozas I., Alkorta I., Elguero J. Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors. J. Am. Chem. Soc. 2000, 122:11154-11161.
49. Reed A.E., Curtiss L.A., Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88:899-926.
50. Li P., Bu Y., Ai H. Theoretical determinations of ionization potential and electron affinity of glycinamide using density functional theory. J. Phys. Chem. A 2004, 108:1200-1207.
51. Tomasi J., Mennucci B., Cammi R. Quantum mechanical continuum solvation models. Chem. Rev. 2005, 105:2999-3093.
52. MiertuŠ S., Scrocco E., Tomasi J. Electrostatic interaction of a solute with a continuum. A direct utilizaion of ab initio molecular potentials for the prevision of solvent effects. Chem. Phys. 1981, 55:117-129.
53. Marenich A.V., Cramer C.J., Truhlar D.G. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J. Phys. Chem. B 2009, 113:6378-6396.
54. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Gaussian, Inc., Wallingford CT, 2009.