메뉴 건너뛰기




Volumn 48, Issue 18, 2014, Pages 10904-10911

Dehalogenation of aromatics by nucleophilic aromatic substitution

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC HYDROCARBONS; NUCLEOPHILES; SUBSTITUTION REACTIONS;

EID: 84924785799     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es5028822     Document Type: Article
Times cited : (36)

References (52)
  • 1
    • 0028811783 scopus 로고
    • Global usage of selected persistent organochlorines
    • Voldner, E. C.; Li, Y.-F. Global usage of selected persistent organochlorines. Sci. Total Environ. 1995, 160-161, 201-210.
    • (1995) Sci. Total Environ. , vol.160-161 , pp. 201-210
    • Voldner, E.C.1    Li, Y.-F.2
  • 2
    • 34247537515 scopus 로고    scopus 로고
    • Towards a global historical emission inventory for selected PCB congeners-A mass balance approach: 3. An update
    • Breivik, K.; Sweetman, A.; Pacyna, J. M.; Jones, K. C. Towards a global historical emission inventory for selected PCB congeners-A mass balance approach: 3. An update. Sci. Total Environ. 2007, 377, 296-307.
    • (2007) Sci. Total Environ. , vol.377 , pp. 296-307
    • Breivik, K.1    Sweetman, A.2    Pacyna, J.M.3    Jones, K.C.4
  • 3
    • 35348891404 scopus 로고    scopus 로고
    • Global fate of POPs: Current and future research directions
    • Lohmann, R.; Breivik, K.; Dachs, J.; Muir, D. Global fate of POPs: Current and future research directions. Environ. Pollut. 2007, 150, 150-165.
    • (2007) Environ. Pollut. , vol.150 , pp. 150-165
    • Lohmann, R.1    Breivik, K.2    Dachs, J.3    Muir, D.4
  • 4
    • 0036223196 scopus 로고    scopus 로고
    • An overview of brominated flame retardants in the environment
    • de Wit, C. A. An overview of brominated flame retardants in the environment. Chemosphere 2002, 46, 583-624.
    • (2002) Chemosphere , vol.46 , pp. 583-624
    • De Wit, C.A.1
  • 8
    • 23244462832 scopus 로고    scopus 로고
    • Neilson, A., Ed.; Springer: Berlin, Heidelberg, The Handbook of Environmental Chemistry
    • Neilson, A.; Allard, A.-S. In Organofluorines; Neilson, A., Ed.; Springer: Berlin, Heidelberg, 2002; The Handbook of Environmental Chemistry, Vol. 3 N; pp 137-202.
    • (2002) Organofluorines , vol.3 N , pp. 137-202
    • Neilson, A.1    Allard, A.-S.2
  • 10
    • 77958039726 scopus 로고    scopus 로고
    • Fluorine in health care: Organofluorine containing blockbuster drugs
    • O'Hagan, D. Fluorine in health care: Organofluorine containing blockbuster drugs. J. Fluorine Chem. 2010, 131, 1071-1081.
    • (2010) J. Fluorine Chem. , vol.131 , pp. 1071-1081
    • O'Hagan, D.1
  • 11
    • 84890577656 scopus 로고    scopus 로고
    • Thermochemical factors affecting the dehalogenation of aromatics
    • Sadowsky, D.; McNeill, K.; Cramer, C. J. Thermochemical factors affecting the dehalogenation of aromatics. Environ. Sci. Technol. 2013, 47, 14194-14203.
    • (2013) Environ. Sci. Technol. , vol.47 , pp. 14194-14203
    • Sadowsky, D.1    McNeill, K.2    Cramer, C.J.3
  • 12
    • 0010820910 scopus 로고
    • Activation of carbon-fluorine bonds by metal complexes bond activation with mechanisms
    • Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Activation of carbon-fluorine bonds by metal complexes bond activation with mechanisms. Chem. Rev. 1994, 94, 373-431.
    • (1994) Chem. Rev. , vol.94 , pp. 373-431
    • Kiplinger, J.L.1    Richmond, T.G.2    Osterberg, C.E.3
  • 14
    • 0036860845 scopus 로고    scopus 로고
    • Metal-mediated reductive hydrodehalogenation of organic halides
    • Alonso, F.; Beletskaya, I. P.; Yus, M. Metal-mediated reductive hydrodehalogenation of organic halides. Chem. Rev. 2002, 102, 4009-4092.
    • (2002) Chem. Rev. , vol.102 , pp. 4009-4092
    • Alonso, F.1    Beletskaya, I.P.2    Yus, M.3
  • 15
    • 0037764840 scopus 로고    scopus 로고
    • Solid state dehalogenation of PCBs in contaminated soil using NaBH4
    • Aresta, M.; Caramuscio, P.; De Stefano, L.; Pastore, T. Solid state dehalogenation of PCBs in contaminated soil using NaBH4. Waste Manage. 2003, 23, 315-319.
    • (2003) Waste Manage. , vol.23 , pp. 315-319
    • Aresta, M.1    Caramuscio, P.2    De Stefano, L.3    Pastore, T.4
  • 17
    • 0036915878 scopus 로고    scopus 로고
    • Hydrodechlorination of trichloroethylene to hydrocarbons using bimetallic nickel-iron nanoparticles
    • Schrick, B.; Blough, J. L.; Jones, A. D.; Mallouk, T. E. Hydrodechlorination of trichloroethylene to hydrocarbons using bimetallic nickel-iron nanoparticles. Chem. Mater. 2002, 14, 5140-5147.
    • (2002) Chem. Mater. , vol.14 , pp. 5140-5147
    • Schrick, B.1    Blough, J.L.2    Jones, A.D.3    Mallouk, T.E.4
  • 19
    • 0000603607 scopus 로고
    • Fluoride ion as a nucleophile and a leaving group in aromatic nucleophilic substitution reactions
    • Vlasov, V. Fluoride ion as a nucleophile and a leaving group in aromatic nucleophilic substitution reactions. J. Fluorine Chem. 1993, 61, 193-216.
    • (1993) J. Fluorine Chem. , vol.61 , pp. 193-216
    • Vlasov, V.1
  • 20
    • 0001677496 scopus 로고    scopus 로고
    • Recent advances in C-F bond activation
    • Burdeniuc, J.; Jedicka, B.; Crabtree, R. H. Recent advances in C-F bond activation. Chem. Ber. 1997, 130, 145-154.
    • (1997) Chem. Ber. , vol.130 , pp. 145-154
    • Burdeniuc, J.1    Jedicka, B.2    Crabtree, R.H.3
  • 21
    • 66249097754 scopus 로고    scopus 로고
    • C-F bond activation in organic synthesis
    • Amii, H.; Uneyama, K. C-F bond activation in organic synthesis. Chem. Rev. 2009, 109, 2119-2183.
    • (2009) Chem. Rev. , vol.109 , pp. 2119-2183
    • Amii, H.1    Uneyama, K.2
  • 22
    • 0031040424 scopus 로고    scopus 로고
    • Mechanism of nucleophilic aromatic substitution of 1-chloro-2, 4-dinitrobenzene by glutathione in the gas phase and in solution. Implications for the mode of action of glutathione S-transferases
    • Zheng, Y.-J.; Ornstein, R. L. Mechanism of nucleophilic aromatic substitution of 1-chloro-2, 4-dinitrobenzene by glutathione in the gas phase and in solution. Implications for the mode of action of glutathione S-transferases. J. Am. Chem. Soc. 1997, 119, 648-655.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 648-655
    • Zheng, Y.-J.1    Ornstein, R.L.2
  • 24
    • 6444229663 scopus 로고    scopus 로고
    • QM/MM studies of the enzyme-catalyzed dechlorination of 4-chlorobenzoyl-CoA provide insight into reaction energetics
    • Xu, D.; Wei, Y.; Wu, J.; Dunaway-Mariano, D.; Guo, H.; Cui, Q.; Gao, J. QM/MM studies of the enzyme-catalyzed dechlorination of 4-chlorobenzoyl-CoA provide insight into reaction energetics. J. Am. Chem. Soc. 2004, 126, 13649-13658.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13649-13658
    • Xu, D.1    Wei, Y.2    Wu, J.3    Dunaway-Mariano, D.4    Guo, H.5    Cui, Q.6    Gao, J.7
  • 25
    • 0023857692 scopus 로고
    • Dissection of the catalytic mechanism of isozyme 4-4 of glutathione S-transferase with alternative substrates
    • Chen, W. J.; Graminski, G. F.; Armstrong, R. N. Dissection of the catalytic mechanism of isozyme 4-4 of glutathione S-transferase with alternative substrates. Biochemistry 1988, 27, 647-654.
    • (1988) Biochemistry , vol.27 , pp. 647-654
    • Chen, W.J.1    Graminski, G.F.2    Armstrong, R.N.3
  • 26
    • 0001474192 scopus 로고
    • A surprising effect of leaving group on the nucleophilic aromatic substitution reaction catalyzed by 4-chlorobenzoyl CoA dehalogenase
    • Crooks, G. P.; Copley, S. D. A surprising effect of leaving group on the nucleophilic aromatic substitution reaction catalyzed by 4-chlorobenzoyl CoA dehalogenase. J. Am. Chem. Soc. 1993, 115, 6422-6423.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6422-6423
    • Crooks, G.P.1    Copley, S.D.2
  • 27
    • 0042837252 scopus 로고
    • ∗ orbital mixing for the nucleophilic displacement on the unsaturated carbon
    • ∗ orbital mixing for the nucleophilic displacement on the unsaturated carbon. Can. J. Chem. 1984, 62, 235-240.
    • (1984) Can. J. Chem. , vol.62 , pp. 235-240
    • Yamabe, S.1    Minato, T.2    Kawabata, Y.3
  • 28
    • 0000799038 scopus 로고    scopus 로고
    • Single-step and multistep mechanisms of aromatic nucleophilic substitution of halobenzenes and halonitrobenzenes with halide anions: Ab initio computational study
    • Glukhovtsev, M. N.; Bach, R. D.; Laiter, S. Single-step and multistep mechanisms of aromatic nucleophilic substitution of halobenzenes and halonitrobenzenes with halide anions: Ab initio computational study. J. Org. Chem. 1997, 62, 4036-4046.
    • (1997) J. Org. Chem. , vol.62 , pp. 4036-4046
    • Glukhovtsev, M.N.1    Bach, R.D.2    Laiter, S.3
  • 29
    • 77951819859 scopus 로고    scopus 로고
    • Rate-determining factors in nucleophilic aromatic substitution reactions
    • Fernández, I.; Frenking, G.; Uggerud, E. Rate-determining factors in nucleophilic aromatic substitution reactions. J. Org. Chem. 2010, 75, 2971-2980.
    • (2010) J. Org. Chem. , vol.75 , pp. 2971-2980
    • Fernández, I.1    Frenking, G.2    Uggerud, E.3
  • 30
    • 0024678923 scopus 로고
    • Groundwater contamination: Pump-and-treat remediation
    • Mackay, D. M.; Cherry, J. A. Groundwater contamination: pump-and-treat remediation. Environ. Sci. Technol. 1989, 23, 630-636.
    • (1989) Environ. Sci. Technol. , vol.23 , pp. 630-636
    • Mackay, D.M.1    Cherry, J.A.2
  • 32
    • 0034919821 scopus 로고    scopus 로고
    • Estimates of hydride ion stability in condensed systems: Energy of formation and solvation in aqueous and polar-organic solvents
    • Kelly, C.; Rosseinsky, D. Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents. Phys. Chem. Chem. Phys. 2001, 3, 2086-2090.
    • (2001) Phys. Chem. Chem. Phys. , vol.3 , pp. 2086-2090
    • Kelly, C.1    Rosseinsky, D.2
  • 33
    • 43049141516 scopus 로고    scopus 로고
    • The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals
    • Zhao, Y.; Truhlar, D. G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 2008, 120, 215-241.
    • (2008) Theor. Chem. Acc. , vol.120 , pp. 215-241
    • Zhao, Y.1    Truhlar, D.G.2
  • 34
    • 40549127108 scopus 로고    scopus 로고
    • Density functionals with broad applicability in chemistry
    • Zhao, Y.; Truhlar, D. G. Density functionals with broad applicability in chemistry. Acc. Chem. Res. 2008, 41, 157-167.
    • (2008) Acc. Chem. Res. , vol.41 , pp. 157-167
    • Zhao, Y.1    Truhlar, D.G.2
  • 35
    • 79952599241 scopus 로고    scopus 로고
    • Density functional theory for reaction energies: Test of meta and hybrid meta functionals, range-separated functionals, and other high-performance functionals
    • Zhao, Y.; Truhlar, D. G. Density functional theory for reaction energies: Test of meta and hybrid meta functionals, range-separated functionals, and other high-performance functionals. J. Chem. Theory Comput. 2011, 7, 669-676.
    • (2011) J. Chem. Theory Comput. , vol.7 , pp. 669-676
    • Zhao, Y.1    Truhlar, D.G.2
  • 36
    • 84877027495 scopus 로고    scopus 로고
    • Hierarchy of relative bond dissociation enthalpies and their use to efficiently compute accurate absolute bond dissociation enthalpies for C-H, C-C, and C-F Bonds
    • Chan, B.; Radom, L. Hierarchy of relative bond dissociation enthalpies and their use to efficiently compute accurate absolute bond dissociation enthalpies for C-H, C-C, and C-F Bonds. J. Phys. Chem. A 2013, 117, 3666-3675.
    • (2013) J. Phys. Chem. A , vol.117 , pp. 3666-3675
    • Chan, B.1    Radom, L.2
  • 37
    • 66349120487 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2009) J. Phys. Chem. B , vol.113 , pp. 6378-6396
    • Marenich, A.V.1    Cramer, C.J.2    Truhlar, D.G.3
  • 38
    • 77956602800 scopus 로고    scopus 로고
    • Computational thermochemistry: Scale factor databases and scale factors for vibrational frequencies obtained from electronic model chemistries
    • Alecu, I. M.; Zheng, J.; Zhao, Y.; Truhlar, D. G. Computational thermochemistry: Scale factor databases and scale factors for vibrational frequencies obtained from electronic model chemistries. J. Chem. Theory Comput. 2010, 6, 2872-2887.
    • (2010) J. Chem. Theory Comput. , vol.6 , pp. 2872-2887
    • Alecu, I.M.1    Zheng, J.2    Zhao, Y.3    Truhlar, D.G.4
  • 41
    • 32244447508 scopus 로고
    • Nucleophilic displacement in polyhalogenoaromatic compounds. Part 12. Additivity of fluorine substituent effects in methoxydefluorination
    • Bolton, R.; Sandall, J. Nucleophilic displacement in polyhalogenoaromatic compounds. Part 12. Additivity of fluorine substituent effects in methoxydefluorination. J. Fluorine Chem. 1982, 21, 459-467.
    • (1982) J. Fluorine Chem. , vol.21 , pp. 459-467
    • Bolton, R.1    Sandall, J.2
  • 42
    • 0000252375 scopus 로고
    • Kinetics of nucleophilic substitution reactions of polyfluoroaromatic compounds
    • Rodionov, P.; Furin, G. Kinetics of nucleophilic substitution reactions of polyfluoroaromatic compounds. J. Fluorine Chem. 1990, 47, 361-434.
    • (1990) J. Fluorine Chem. , vol.47 , pp. 361-434
    • Rodionov, P.1    Furin, G.2
  • 43
    • 84877857257 scopus 로고    scopus 로고
    • Does the molecular electrostatic potential reflect the effects of substituents in aromatic systems?
    • Galabov, B.; Nikolova, V.; Ilieva, S. Does the Molecular Electrostatic Potential Reflect the Effects of Substituents in Aromatic Systems? Chem.-Eur. J. 2013, 19, 5149-5155.
    • (2013) Chem.-Eur. J. , vol.19 , pp. 5149-5155
    • Galabov, B.1    Nikolova, V.2    Ilieva, S.3
  • 44
    • 37049097745 scopus 로고
    • Mechanisms for reactions of halogenated compounds. Part 2. Orienting effects of chlorine substituents in nucleophilic aromatic substitution
    • Chambers, R. D.; Close, D.; Musgrave, W. K. R.; Waterhouse, J. S.; Williams, D. L. H. Mechanisms for reactions of halogenated compounds. Part 2. Orienting effects of chlorine substituents in nucleophilic aromatic substitution. J. Chem. Soc., Perkin Trans. 2 1977, 1774-1778.
    • (1977) J. Chem. Soc., Perkin Trans. 2 , pp. 1774-1778
    • Chambers, R.D.1    Close, D.2    Musgrave, W.K.R.3    Waterhouse, J.S.4    Williams, D.L.H.5
  • 45
    • 33947440291 scopus 로고
    • Atomic radii and interatomic distances in metals
    • Pauling, L. Atomic radii and interatomic distances in metals. J. Am. Chem. Soc. 1947, 69, 542-553.
    • (1947) J. Am. Chem. Soc. , vol.69 , pp. 542-553
    • Pauling, L.1
  • 46
    • 84857099445 scopus 로고    scopus 로고
    • Charge Model 5: An extension of Hirshfeld Population Analysis for the accurate description of molecular interactions in gaseous and condensed phases
    • Marenich, A. V.; Jerome, S. V.; Cramer, C. J.; Truhlar, D. G. Charge Model 5: An extension of Hirshfeld Population Analysis for the accurate description of molecular interactions in gaseous and condensed phases. J. Chem. Theory Comput. 2012, 8, 527-541.
    • (2012) J. Chem. Theory Comput. , vol.8 , pp. 527-541
    • Marenich, A.V.1    Jerome, S.V.2    Cramer, C.J.3    Truhlar, D.G.4
  • 47
    • 0000139224 scopus 로고
    • Single electron transfer in reactions of alkyl halides with lithium thiolates
    • Ashby, E. C.; Park, W. S.; Goel, A. B.; Su, W. Y. Single electron transfer in reactions of alkyl halides with lithium thiolates. J. Org. Chem. 1985, 50, 5184-5193.
    • (1985) J. Org. Chem. , vol.50 , pp. 5184-5193
    • Ashby, E.C.1    Park, W.S.2    Goel, A.B.3    Su, W.Y.4
  • 48
    • 0037239899 scopus 로고    scopus 로고
    • Nucleophilic substitution reactions by electron transfer
    • Rossi, R. A.; Pierini, A. B.; Penéñory, A. B. Nucleophilic substitution reactions by electron transfer. Chem. Rev. 2002, 103, 71-168.
    • (2002) Chem. Rev. , vol.103 , pp. 71-168
    • Rossi, R.A.1    Pierini, A.B.2    Penéñory, A.B.3
  • 49
    • 0000135146 scopus 로고
    • A rationalization of orientation and reactivity in the nucleophilic replacement reactions of aromatic polyhalo-compounds
    • Burdon, J. A rationalization of orientation and reactivity in the nucleophilic replacement reactions of aromatic polyhalo-compounds. Tetrahedron 1965, 21, 3373-3380.
    • (1965) Tetrahedron , vol.21 , pp. 3373-3380
    • Burdon, J.1
  • 50
    • 0005667409 scopus 로고
    • New reactions of polyfluoroaromatic compounds. Pentafluorophenylalanine and tetrafluorotyrosine
    • Filler, R.; Ayyangar, N. R.; Gustowski, W.; Kang, H. H. New reactions of polyfluoroaromatic compounds. Pentafluorophenylalanine and tetrafluorotyrosine. J. Org. Chem. 1969, 34, 534-538.
    • (1969) J. Org. Chem. , vol.34 , pp. 534-538
    • Filler, R.1    Ayyangar, N.R.2    Gustowski, W.3    Kang, H.H.4
  • 51
    • 0001133615 scopus 로고
    • Aromatic polyfluorocompounds. Part LVIII. The reaction of n-butyllithium with metnyl-, fluoromethyl-, and difluorometnyl-pentafluorobenzene
    • Coe, P. L.; Oldfield, D.; Tatlow, J. C. Aromatic polyfluorocompounds. Part LVIII. The reaction of n-butyllithium with metnyl-, fluoromethyl-, and difluorometnyl-pentafluorobenzene. J. Fluorine Chem. 1985, 29, 341-347.
    • (1985) J. Fluorine Chem. , vol.29 , pp. 341-347
    • Coe, P.L.1    Oldfield, D.2    Tatlow, J.C.3
  • 52
    • 84879235824 scopus 로고    scopus 로고
    • Complete hydrodehalogenation of polyfluorinated and other polyhalogenated benzenes under mild catalytic conditions
    • Baumgartner, R.; Stieger, G. K.; McNeill, K. Complete hydrodehalogenation of polyfluorinated and other polyhalogenated benzenes under mild catalytic conditions. Environ. Sci. Technol. 2013, 47, 6545-6553.
    • (2013) Environ. Sci. Technol. , vol.47 , pp. 6545-6553
    • Baumgartner, R.1    Stieger, G.K.2    McNeill, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.