Factors influencing C-ON bond homolysis in alkoxyamines: Unexpected behavior of SG1 (N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl) -N-oxyl)-based alkoxyamines

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 4925-4930

  Bertin, Denis ^a   Gigmes, Didier ^a   Le Mercier, Christophe ^a   Marque, Sylvain R A ^a   Tordo, Paul ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; OXIDES; POLYMERIZATION; POLYMERS; RATE CONSTANTS; REACTION KINETICS;

CLEAVAGE TEMPERATURES; EQUILIBRIUM CONSTANT; HOMOLYSIS;

AMINES;

ALKYL GROUP; AMINE; CARBON; MONOMER; N (2 METHYL 2 PROPYL) N (1 DIETHYLPHOSPHONO 2,2 DIMETHYLPROPYL) N OXYL; NITROGEN; NITROXIDE; OXYGEN; POLYMER; RADICAL; TEMPOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CORRELATION COEFFICIENT; EQUILIBRIUM CONSTANT; HOMOLYSIS; LYSIS; POLARIZATION; POLYMERIZATION; TEMPERATURE;

EID: 3542996292     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0495586     Document Type: Article

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72. 6 was used): McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493. BDE(10-H) = 385.0(150) kJ/mol: Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1997, 119, 12869. BDE-(13-H) = 406.3(105) kJ/mol: Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003; p 66. BDE(8-H) = 375.8 kJ/mol, BDE(12-H) = 396.3 kJ/mol: King, K. D.; Goddard, R. D. J. Phys. Chem. 1976, 80, 546. BDE(3-H) = 368.8-(88) kJ/mol, BDE(4-H) = 370(63) kJ/mol, BDE(5-H) = 404.0(17) kJ/mol: Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744. BDE(11-H) = BDE(10-H) + 9.5 kJ/mol = 394.5 (4) kJ/mol, increment from: Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750. BDE(6-H) = 399.6 (40) kJ/mol: CRC Handbook of Chemistry and Physics, 76th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995; pp 9-64.
73. 6 was used): McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493. BDE(10-H) = 385.0(150) kJ/mol: Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1997, 119, 12869. BDE-(13-H) = 406.3(105) kJ/mol: Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003; p 66. BDE(8-H) = 375.8 kJ/mol, BDE(12-H) = 396.3 kJ/mol: King, K. D.; Goddard, R. D. J. Phys. Chem. 1976, 80, 546. BDE(3-H) = 368.8-(88) kJ/mol, BDE(4-H) = 370(63) kJ/mol, BDE(5-H) = 404.0(17) kJ/mol: Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744. BDE(11-H) = BDE(10-H) + 9.5 kJ/mol = 394.5 (4) kJ/mol, increment from: Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750. BDE(6-H) = 399.6 (40) kJ/mol: CRC Handbook of Chemistry and Physics, 76th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995; pp 9-64.
74. 6 was used): McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493. BDE(10-H) = 385.0(150) kJ/mol: Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1997, 119, 12869. BDE-(13-H) = 406.3(105) kJ/mol: Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003; p 66. BDE(8-H) = 375.8 kJ/mol, BDE(12-H) = 396.3 kJ/mol: King, K. D.; Goddard, R. D. J. Phys. Chem. 1976, 80, 546. BDE(3-H) = 368.8-(88) kJ/mol, BDE(4-H) = 370(63) kJ/mol, BDE(5-H) = 404.0(17) kJ/mol: Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744. BDE(11-H) = BDE(10-H) + 9.5 kJ/mol = 394.5 (4) kJ/mol, increment from: Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750. BDE(6-H) = 399.6 (40) kJ/mol: CRC Handbook of Chemistry and Physics, 76th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995; pp 9-64.
75. 6 was used): McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493. BDE(10-H) = 385.0(150) kJ/mol: Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1997, 119, 12869. BDE-(13-H) = 406.3(105) kJ/mol: Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003; p 66. BDE(8-H) = 375.8 kJ/mol, BDE(12-H) = 396.3 kJ/mol: King, K. D.; Goddard, R. D. J. Phys. Chem. 1976, 80, 546. BDE(3-H) = 368.8-(88) kJ/mol, BDE(4-H) = 370(63) kJ/mol, BDE(5-H) = 404.0(17) kJ/mol: Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744. BDE(11-H) = BDE(10-H) + 9.5 kJ/mol = 394.5 (4) kJ/mol, increment from: Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750. BDE(6-H) = 399.6 (40) kJ/mol: CRC Handbook of Chemistry and Physics, 76th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995; pp 9-64.
76. 6 was used): McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493. BDE(10-H) = 385.0(150) kJ/mol: Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1997, 119, 12869. BDE-(13-H) = 406.3(105) kJ/mol: Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003; p 66. BDE(8-H) = 375.8 kJ/mol, BDE(12-H) = 396.3 kJ/mol: King, K. D.; Goddard, R. D. J. Phys. Chem. 1976, 80, 546. BDE(3-H) = 368.8-(88) kJ/mol, BDE(4-H) = 370(63) kJ/mol, BDE(5-H) = 404.0(17) kJ/mol: Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744. BDE(11-H) = BDE(10-H) + 9.5 kJ/mol = 394.5 (4) kJ/mol, increment from: Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750. BDE(6-H) = 399.6 (40) kJ/mol: CRC Handbook of Chemistry and Physics, 76th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995; pp 9-64.
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