메뉴 건너뛰기




Volumn 121, Issue 36, 1999, Pages 8366-8372

From benzene to muconaldehyde: Theoretical mechanistic investigation on some tropospheric oxidation channels

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; MUCONALDEHYDE; NITROGEN OXIDE;

EID: 0033568721     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990552l     Document Type: Article
Times cited : (48)

References (49)
  • 1
    • 0001486283 scopus 로고    scopus 로고
    • Free Radicals in the Atmosphere: The Motor of Tropospheric Oxidation Processes
    • Minisci, F., Ed.; Kluwer Academic Publishers: The Netherlands, Chapter 27, and references therein
    • (a) Becker, K. H.; Barnes, I.; Ruppert, L.; Wiesen, P. Free Radicals in the Atmosphere: the Motor of Tropospheric Oxidation Processes. In Free Radicals in Biology and Environment; Minisci, F., Ed.; Kluwer Academic Publishers: The Netherlands, 1997; Chapter 27, pp 365-385, and references therein.
    • (1997) Free Radicals in Biology and Environment , pp. 365-385
    • Becker, K.H.1    Barnes, I.2    Ruppert, L.3    Wiesen, P.4
  • 2
    • 0001565334 scopus 로고    scopus 로고
    • Degradation of Atmospheric Pollutants by Tropospheric Free Radical Reactions
    • Minisci, F., Ed.; Kluwer Academic Publishers: The Netherlands, Chapter 28
    • (b) Güsten, H. Degradation of Atmospheric Pollutants by Tropospheric Free Radical Reactions. In Free Radicals in Biology and Environment; Minisci, F., Ed.; Kluwer Academic Publishers: The Netherlands, 1997; Chapter 28, 387-408.
    • (1997) Free Radicals in Biology and Environment , pp. 387-408
    • Güsten, H.1
  • 4
    • 0003308733 scopus 로고
    • Reactions of Oxygen Species in the Atmosphere
    • Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional: New York, Chapter 7
    • Atkinson, R. Reactions of Oxygen Species in the Atmosphere. In Active Oxygen in Chemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional: New York, 1995; Chapter 7.
    • (1995) Active Oxygen in Chemistry
    • Atkinson, R.1
  • 7
    • 0000146030 scopus 로고
    • Monograph No. 2
    • Atkinson, R. J. Phys. Chem. Ref. Data 1994, Monograph No. 2, 1-216; ibid., 1989, Monograph No. 1, 1-246.
    • (1994) J. Phys. Chem. Ref. Data , pp. 1-216
    • Atkinson, R.1
  • 8
    • 0344961573 scopus 로고
    • Monograph No. 1
    • Atkinson, R. J. Phys. Chem. Ref. Data 1994, Monograph No. 2, 1-216; ibid., 1989, Monograph No. 1, 1-246.
    • (1989) J. Phys. Chem. Ref. Data , pp. 1-246
  • 16
    • 0021282870 scopus 로고
    • (a) Dumdei, B. E.; O'Brien R. J. Nature 1984, 311, 248-250. Yu, J.; Jeffries, H. E.; Sexton, K. G. Atmos. Environ. 1997, 31, 2261-2280.
    • (1984) Nature , vol.311 , pp. 248-250
    • Dumdei, B.E.1    O'Brien, R.J.2
  • 21
    • 0004240372 scopus 로고    scopus 로고
    • Clarendon Press: Oxford, U.K.
    • Wayne, R. P. Chemistry of Atmospheres; Clarendon Press: Oxford, U.K., 1996; pp 252-263.
    • (1996) Chemistry of Atmospheres , pp. 252-263
    • Wayne, R.P.1
  • 22
    • 0001541544 scopus 로고
    • Exploration of Selected Pathways for Metabolic Oxidative Ring Opening of Benzene Based on Estimates of Molecular Energetics
    • Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapmann & Hall: New York, Chapter 8
    • (a) Greenberg, A. Exploration of Selected Pathways for Metabolic Oxidative Ring Opening of Benzene Based on Estimates of Molecular Energetics. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapmann & Hall: New York, 1995; Chapter 8, pp 413-417.
    • (1995) Active Oxygen in Biochemistry , pp. 413-417
    • Greenberg, A.1
  • 24
    • 0000582695 scopus 로고
    • Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Schlegel, H. B. In Computational Theoretical Organic Chemistry, Csizsmadia, I. G., Daudel, Eds.; Reidel Publ. Co.: Boston, MA, 1981; pp 129-159. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681; Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976- 1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
    • (1992) Chem. Phys. Lett. , vol.199 , pp. 557-560
    • Pople, J.A.1    Gill, P.M.W.2    Johnson, B.G.3
  • 25
    • 0002929062 scopus 로고
    • Csizsmadia, I. G., Daudel, Eds.; Reidel Publ. Co.: Boston, MA
    • Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Schlegel, H. B. In Computational Theoretical Organic Chemistry, Csizsmadia, I. G., Daudel, Eds.; Reidel Publ. Co.: Boston, MA, 1981; pp 129-159. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681; Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976- 1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
    • (1981) Computational Theoretical Organic Chemistry , pp. 129-159
    • Schlegel, H.B.1
  • 26
    • 36749111412 scopus 로고
    • Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Schlegel, H. B. In Computational Theoretical Organic Chemistry, Csizsmadia, I. G., Daudel, Eds.; Reidel Publ. Co.: Boston, MA, 1981; pp 129-159. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681; Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976- 1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
    • (1982) J. Chem. Phys. , vol.77 , pp. 3676-3681
    • Schlegel, H.B.1
  • 27
    • 36549098657 scopus 로고
    • Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Schlegel, H. B. In Computational Theoretical Organic Chemistry, Csizsmadia, I. G., Daudel, Eds.; Reidel Publ. Co.: Boston, MA, 1981; pp 129-159. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681; Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
    • (1984) J. Chem. Phys. , vol.80 , pp. 1976-1981
    • Schlegel, H.B.1    Binkley, J.S.2    Pople, J.A.3
  • 28
    • 84986439201 scopus 로고
    • Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Schlegel, H. B. In Computational Theoretical Organic Chemistry, Csizsmadia, I. G., Daudel, Eds.; Reidel Publ. Co.: Boston, MA, 1981; pp 129-159. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681; Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976- 1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
    • (1982) J. Comput. Chem. , vol.3 , pp. 214-218
    • Schlegel, H.B.1
  • 29
    • 0003569570 scopus 로고
    • Oxford University Press: New York, Chapter 3.
    • Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989; Chapter 3. Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100. Becke A. D. ACS Symp. Ser. 1989, 394, 165. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Becke, A. D. J. Chem. Phys 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
    • (1989) Density Functional Theory of Atoms and Molecules
    • Parr, R.G.1    Yang, W.2
  • 30
    • 4243553426 scopus 로고
    • Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989; Chapter 3. Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100. Becke A. D. ACS Symp. Ser. 1989, 394, 165. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Becke, A. D. J. Chem. Phys 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
    • (1988) Phys. Rev. A: At., Mol., Opt. Phys. , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 31
    • 0000721485 scopus 로고
    • Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989; Chapter 3. Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100. Becke A. D. ACS Symp. Ser. 1989, 394, 165. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Becke, A. D. J. Chem. Phys 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
    • (1989) ACS Symp. Ser. , vol.394 , pp. 165
    • Becke, A.D.1
  • 32
    • 0000582695 scopus 로고
    • Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989; Chapter 3. Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100. Becke A. D. ACS Symp. Ser. 1989, 394, 165. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Becke, A. D. J. Chem. Phys 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
    • (1992) Chem. Phys. Lett. , vol.199 , pp. 557-560
    • Pople, J.A.1    Gill, P.M.W.2    Johnson, B.G.3
  • 33
    • 0000189651 scopus 로고
    • Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989; Chapter 3. Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100. Becke A. D. ACS Symp. Ser. 1989, 394, 165. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Becke, A. D. J. Chem. Phys 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
    • (1993) J. Chem. Phys , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 34
    • 0345491105 scopus 로고
    • Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989; Chapter 3. Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100. Becke A. D. ACS Symp. Ser. 1989, 394, 165. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557-560. Becke, A. D. J. Chem. Phys 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
    • (1988) Phys. Rev. B: Condens. Matter , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 35
    • 0001447227 scopus 로고    scopus 로고
    • This theory level was tested on a model reaction and compared with more expensive ab initio methods: Ghigo, G.; Tonachini, G. J. Chem. Phys. 1999, 109, 7298-7304. It appeared to be a rather good compromise between reliability and feasibility in studying the degradation of aromatics.
    • (1999) J. Chem. Phys. , vol.109 , pp. 7298-7304
    • Ghigo, G.1    Tonachini, G.2
  • 37
    • 33748545144 scopus 로고
    • (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
    • (1973) Theor. Chim. Acta , vol.28 , pp. 213-222
    • Hariharan, P.C.1    Pople, J.A.2
  • 40
    • 0001990757 scopus 로고
    • Yamanaka, S.; Kawakami, T.; Nagao K.; Yamaguchi, K. Chem. Phys. Lett. 1994, 231, 25-33. Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537-542. See also: Baker, J.; Scheiner, A.; Andzelm, J. Chem. Phys. Lett. 1993, 216, 380-388.
    • (1994) Chem. Phys. Lett. , vol.231 , pp. 25-33
    • Yamanaka, S.1    Kawakami, T.2    Nagao, K.3    Yamaguchi, K.4
  • 41
    • 45449124752 scopus 로고
    • Yamanaka, S.; Kawakami, T.; Nagao K.; Yamaguchi, K. Chem. Phys. Lett. 1994, 231, 25-33. Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537-542. See also: Baker, J.; Scheiner, A.; Andzelm, J. Chem. Phys. Lett. 1993, 216, 380-388.
    • (1988) Chem. Phys. Lett. , vol.149 , pp. 537-542
    • Yamaguchi, K.1    Jensen, F.2    Dorigo, A.3    Houk, K.N.4
  • 42
    • 0000753626 scopus 로고
    • Yamanaka, S.; Kawakami, T.; Nagao K.; Yamaguchi, K. Chem. Phys. Lett. 1994, 231, 25-33. Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537-542. See also: Baker, J.; Scheiner, A.; Andzelm, J. Chem. Phys. Lett. 1993, 216, 380-388.
    • (1993) Chem. Phys. Lett. , vol.216 , pp. 380-388
    • Baker, J.1    Scheiner, A.2    Andzelm, J.3
  • 43
    • 0000886316 scopus 로고    scopus 로고
    • For discussions concerning the effect of spin projection on the performances of DFT methods, see: Wittbrodt, J. M.; Schlegel, H. B. J. Chem. Phys. 1996, 105, 6574-6577; Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043.
    • (1996) J. Chem. Phys. , vol.105 , pp. 6574-6577
    • Wittbrodt, J.M.1    Schlegel, H.B.2
  • 44
    • 0030018945 scopus 로고    scopus 로고
    • For discussions concerning the effect of spin projection on the performances of DFT methods, see: Wittbrodt, J. M.; Schlegel, H. B. J. Chem. Phys. 1996, 105, 6574-6577; Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6036-6043
    • Goldstein, E.1    Beno, B.2    Houk, K.N.3
  • 45
    • 0003422992 scopus 로고    scopus 로고
    • Gaussian, Inc.: Pittsburgh, PA
    • Reaction enthalpies were computed as outlined, for instance, in: Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods; Gaussian, Inc.: Pittsburgh, PA, 1996; pp 166-168. McQuarrie, D. A. Statistical Thermodynamics; Harper and Row: New York, 1973; Chapter 8.
    • (1996) Exploring Chemistry with Electronic Structure Methods , pp. 166-168
    • Foresman, J.B.1    Frisch, A.2
  • 46
    • 0004209265 scopus 로고
    • Harper and Row: New York, Chapter 8
    • Reaction enthalpies were computed as outlined, for instance, in: Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods; Gaussian, Inc.: Pittsburgh, PA, 1996; pp 166-168. McQuarrie, D. A. Statistical Thermodynamics; Harper and Row: New York, 1973; Chapter 8.
    • (1973) Statistical Thermodynamics
    • McQuarrie, D.A.1
  • 48
    • 0344961567 scopus 로고    scopus 로고
    • note
    • A typical CPU timing on a DEC Alpha 500/500 station for a single gradient calculation on peroxynitrite V was 96 min; the frequency calculation on the same structure took 25 h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.