메뉴 건너뛰기




Volumn 118, Issue 20, 2014, Pages 5542-5550

PH-sensitive C-ON bond homolysis of alkoxyamines of imidazoline series: A theoretical study

Author keywords

[No Author keywords available]

Indexed keywords

FREE ENERGY; FREE RADICAL REACTIONS; GIBBS FREE ENERGY; PH; POTENTIOMETRIC SENSORS; PROTONATION; THERMOLYSIS;

EID: 84901314713     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp5024372     Document Type: Article
Times cited : (23)

References (45)
  • 2
    • 79960290588 scopus 로고    scopus 로고
    • First Peptide/Protein PEGylation with Functional Polymers Designed by Nitroxide-Mediated Polymerization
    • references therein
    • Chenal, M.; Boursier, C.; Guillaneuf, Y.; Taverna, M.; Couvreura, P.; Nicolas, J. First Peptide/Protein PEGylation with Functional Polymers Designed By Nitroxide-Mediated Polymerization Polym. Chem. 2011, 2, 1523-1530 and references therein.
    • (2011) Polym. Chem. , vol.2 , pp. 1523-1530
    • Chenal, M.1    Boursier, C.2    Guillaneuf, Y.3    Taverna, M.4    Couvreura, P.5    Nicolas, J.6
  • 3
    • 0034299662 scopus 로고    scopus 로고
    • Kinetic Conditions for Living and Controlled Free Radical Polymerizations Mediated by Reversible Combination of Transient Propagating and Persistent Radicals: The Ideal Mechanism
    • Souaille, M.; Fischer, H. Kinetic Conditions for Living and Controlled Free Radical Polymerizations Mediated by Reversible Combination of Transient Propagating and Persistent Radicals: The Ideal Mechanism Macromolecules 2000, 33, 7378-7394
    • (2000) Macromolecules , vol.33 , pp. 7378-7394
    • Souaille, M.1    Fischer, H.2
  • 4
    • 0035781106 scopus 로고    scopus 로고
    • New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations
    • Hawker, C. J.; Bosman, A. W.; Harth, E. New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations Chem. Rev. 2001, 101, 3661-3688
    • (2001) Chem. Rev. , vol.101 , pp. 3661-3688
    • Hawker, C.J.1    Bosman, A.W.2    Harth, E.3
  • 6
    • 84866104848 scopus 로고    scopus 로고
    • On the Origins of Nitroxide Mediated Polymerization (NMP) and Reversible Addition-Fragmentation Chain Transfer (RAFT)
    • Rizzardo, E.; Solomon, D. H. On the Origins of Nitroxide Mediated Polymerization (NMP) and Reversible Addition-Fragmentation Chain Transfer (RAFT) Aust. J. Chem. 2012, 65, 945-969
    • (2012) Aust. J. Chem. , vol.65 , pp. 945-969
    • Rizzardo, E.1    Solomon, D.H.2
  • 7
    • 42549160066 scopus 로고    scopus 로고
    • In-Situ Nitroxide-Mediated Radical Polymerization (NMP) Processes: Their Understanding and Optimization
    • Sciannamea, V.; Jerome, R.; Detrembleur, C. In-Situ Nitroxide-Mediated Radical Polymerization (NMP) Processes: Their Understanding and Optimization Chem. Rev. 2008, 108, 1104-1126
    • (2008) Chem. Rev. , vol.108 , pp. 1104-1126
    • Sciannamea, V.1    Jerome, R.2    Detrembleur, C.3
  • 8
    • 79954609537 scopus 로고    scopus 로고
    • Kinetic Subtleties of Nitroxide Mediated Polymerization
    • Bertin, D.; Gigmes, D.; Marque, S. R. A.; Tordo, P. Kinetic Subtleties of Nitroxide Mediated Polymerization Chem. Soc. Rev. 2011, 40, 2189-2198
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 2189-2198
    • Bertin, D.1    Gigmes, D.2    Marque, S.R.A.3    Tordo, P.4
  • 9
    • 84860823778 scopus 로고    scopus 로고
    • Use of Solvent Effects to Improve Control over Nitroxide-Mediated Polymerization of Isoprene
    • Harrisson, S.; Couvreur, P.; Nicolas, J. Use of Solvent Effects to Improve Control Over Nitroxide-Mediated Polymerization of Isoprene Macromol. Rapid Commun. 2012, 33, 805-810
    • (2012) Macromol. Rapid Commun. , vol.33 , pp. 805-810
    • Harrisson, S.1    Couvreur, P.2    Nicolas, J.3
  • 10
    • 79956150991 scopus 로고    scopus 로고
    • Kinetic Modeling as a Tool to Understand and Improve the Nitroxide Mediated Polymerization of Styrene
    • Bentein, L.; D'hooge, D. R.; Reyniers, M.; Marin, G. B. Kinetic Modeling as a Tool to Understand and Improve the Nitroxide Mediated Polymerization of Styrene Macromol. Theory Simul. 2011, 20, 238-265
    • (2011) Macromol. Theory Simul. , vol.20 , pp. 238-265
    • Bentein, L.1    D'Hooge, D.R.2    Reyniers, M.3    Marin, G.B.4
  • 12
    • 74049149962 scopus 로고    scopus 로고
    • Polystyrene-block-poly(vinyl acetate) through the Use of a Switchable RAFT Agent
    • Benaglia, M.; Chen, M.; Chong, Y.; Moad, G.; Rizzardo, E.; Thang, S. Polystyrene-block-poly(vinyl acetate) through the Use of a Switchable RAFT Agent Macromolecules 2009, 42, 9384-9386
    • (2009) Macromolecules , vol.42 , pp. 9384-9386
    • Benaglia, M.1    Chen, M.2    Chong, Y.3    Moad, G.4    Rizzardo, E.5    Thang, S.6
  • 13
    • 84861406756 scopus 로고    scopus 로고
    • Chain Transfer Kinetics of Acid/Base Switchable N-Aryl-N-Pyridyl Dithiocarbamate RAFT Agents in Methyl Acrylate, N-Vinylcarbazole and Vinyl Acetate Polymerization
    • Keddie, D. J.; Guerrero-Sanchez, C.; Moad, G.; Mulder, R. J.; Rizzardo, E.; Thang, S. H. Chain Transfer Kinetics of Acid/Base Switchable N-Aryl-N-Pyridyl Dithiocarbamate RAFT Agents in Methyl Acrylate, N-Vinylcarbazole and Vinyl Acetate Polymerization Macromolecules 2012, 45, 4205-4215
    • (2012) Macromolecules , vol.45 , pp. 4205-4215
    • Keddie, D.J.1    Guerrero-Sanchez, C.2    Moad, G.3    Mulder, R.J.4    Rizzardo, E.5    Thang, S.H.6
  • 14
    • 79955048994 scopus 로고    scopus 로고
    • First proton triggered C-ON bond homolysis in alkoxyamines
    • Brémondand, P.; Marque, S. R. A. First proton triggered C-ON bond homolysis in alkoxyamines Chem. Commun. 2011, 47, 4291-4293
    • (2011) Chem. Commun. , vol.47 , pp. 4291-4293
    • Brémondand, P.1    Marque, S.R.A.2
  • 15
    • 84856022363 scopus 로고    scopus 로고
    • Chemically Triggered C-ON Bond Homolysis in Alkoxyamines. Part 2: DFT Investigation and Application of the pH Effect on NMP
    • Bagryanskaya, E.; Brémond, P.; Edeleva, M.; Marque, S. R. A.; Parkhomenko, D.; Roubaud, V.; Siri, D. Chemically Triggered C-ON Bond Homolysis in Alkoxyamines. Part 2: DFT Investigation and Application of the pH Effect on NMP Macromol. Rapid Commun. 2012, 33, 152-157
    • (2012) Macromol. Rapid Commun. , vol.33 , pp. 152-157
    • Bagryanskaya, E.1    Brémond, P.2    Edeleva, M.3    Marque, S.R.A.4    Parkhomenko, D.5    Roubaud, V.6    Siri, D.7
  • 16
    • 84855499883 scopus 로고    scopus 로고
    • Chemically Triggered C-ON Bond Homolysis of Alkoxyamines. Quaternization of the Alkyl Fragment
    • Brémond, P.; Koita, A.; Marque, S. R. A.; Pesce, V.; Roubaud, V.; Siri, D. Chemically Triggered C-ON Bond Homolysis of Alkoxyamines. Quaternization of the Alkyl Fragment Org. Lett. 2012, 14, 358-361
    • (2012) Org. Lett. , vol.14 , pp. 358-361
    • Brémond, P.1    Koita, A.2    Marque, S.R.A.3    Pesce, V.4    Roubaud, V.5    Siri, D.6
  • 17
    • 79960156763 scopus 로고    scopus 로고
    • PH-Sensitive C-ON Bond Homolysis of Alkoxyamines of Imidazoline Series with Multiple Ionizable Groups As an Approach for Control of Nitroxide Mediated Polymerization
    • Edeleva, M. V.; Kirilyuk, I. A.; Zhurko, I. F.; Parkhomenko, D. A.; Tsentalovich, Y. P.; Bagryanskaya, E. G. pH-Sensitive C-ON Bond Homolysis of Alkoxyamines of Imidazoline Series with Multiple Ionizable Groups As an Approach for Control of Nitroxide Mediated Polymerization J. Org. Chem. 2011, 76, 5558-5573
    • (2011) J. Org. Chem. , vol.76 , pp. 5558-5573
    • Edeleva, M.V.1    Kirilyuk, I.A.2    Zhurko, I.F.3    Parkhomenko, D.A.4    Tsentalovich, Y.P.5    Bagryanskaya, E.G.6
  • 18
    • 2342580705 scopus 로고    scopus 로고
    • Synthesis of the Tetraethyl Substituted pH-Sensitive Nitroxides of Imidazole Series with Enhanced Stability towards Reduction
    • Kirilyuk, I. A.; Bobko, A. A.; Grigor'ev, I. A.; Khramtsov, V. V. Synthesis of the Tetraethyl Substituted pH-Sensitive Nitroxides of Imidazole Series with Enhanced Stability towards Reduction Org. Biomol. Chem. 2004, 2, 1025-1030
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 1025-1030
    • Kirilyuk, I.A.1    Bobko, A.A.2    Grigor'Ev, I.A.3    Khramtsov, V.V.4
  • 19
    • 33746870806 scopus 로고    scopus 로고
    • Laser Flash Photolysis and CIDNP Studies of Steric Effects on Coupling Rate Constants of Imidazolidine Nitroxide with Carbon-Centered Radicals, Methyl Isobutyrate-2-yl and tert-Butyl Propionate-2-yl
    • Zubenko, D.; Tsentalovich, Y.; Lebedeva, N.; Kirilyuk, I.; Roschchupkina, G.; Zhurko, I.; Reznikov, V.; Marque, S. R. A.; Bagryanskaya, E. Laser Flash Photolysis and CIDNP Studies of Steric Effects on Coupling Rate Constants of Imidazolidine Nitroxide with Carbon-Centered Radicals, Methyl Isobutyrate-2-yl and tert-Butyl Propionate-2-yl J. Org. Chem. 2006, 71, 6044-6052
    • (2006) J. Org. Chem. , vol.71 , pp. 6044-6052
    • Zubenko, D.1    Tsentalovich, Y.2    Lebedeva, N.3    Kirilyuk, I.4    Roschchupkina, G.5    Zhurko, I.6    Reznikov, V.7    Marque, S.R.A.8    Bagryanskaya, E.9
  • 20
    • 78049295724 scopus 로고    scopus 로고
    • Side Reactions of Nitroxide-Mediated Polymerization: N-O versus O-C Cleavage of Alkoxyamines
    • Hodgson, J. L.; Roskop, L. B.; Gordon, M. S.; Lin, C. Y.; Coote, M. L. Side Reactions of Nitroxide-Mediated Polymerization: N-O versus O-C Cleavage of Alkoxyamines J. Phys. Chem. A 2010, 114, 10458-10466
    • (2010) J. Phys. Chem. A , vol.114 , pp. 10458-10466
    • Hodgson, J.L.1    Roskop, L.B.2    Gordon, M.S.3    Lin, C.Y.4    Coote, M.L.5
  • 21
    • 84879077811 scopus 로고    scopus 로고
    • Switching radical stability by pH-induced orbital conversion
    • Gryn'ova, G.; Marshall, D. L.; Blanksby, S. J.; Coote, M. L. Switching radical stability by pH-induced orbital conversion Nat. Chem. 2013, 5, 474-481
    • (2013) Nat. Chem. , vol.5 , pp. 474-481
    • Gryn'Ova, G.1    Marshall, D.L.2    Blanksby, S.J.3    Coote, M.L.4
  • 22
    • 84886873766 scopus 로고    scopus 로고
    • Origin and Scope of Long-Range Stabilizing Interactions and Associated SOMO-HOMO Conversion in Distonic Radical Anions
    • Gryn'ova, G.; Coote, M. L. Origin and Scope of Long-Range Stabilizing Interactions and Associated SOMO-HOMO Conversion in Distonic Radical Anions J. Am. Chem. Soc. 2013, 135, 15392-15403
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 15392-15403
    • Gryn'Ova, G.1    Coote, M.L.2
  • 23
    • 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
  • 24
    • 84961980477 scopus 로고    scopus 로고
    • Quantum Mechanical Continuum Solvation Models
    • Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3094
    • (2005) Chem. Rev. , vol.105 , pp. 2999-3094
    • Tomasi, J.1    Mennucci, B.2    Cammi, R.3
  • 25
    • 83455219492 scopus 로고    scopus 로고
    • Use of Solution-Phase Vibrational Frequencies in Continuum Models for the Free Energy of Solvation
    • Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Use of Solution-Phase Vibrational Frequencies in Continuum Models for the Free Energy of Solvation J. Phys. Chem. B 2011, 115, 14556-14562
    • (2011) J. Phys. Chem. B , vol.115 , pp. 14556-14562
    • Ribeiro, R.F.1    Marenich, A.V.2    Cramer, C.J.3    Truhlar, D.G.4
  • 26
    • 0001264023 scopus 로고    scopus 로고
    • Quantum Mechanical Prediction of the Magnetic Titration Curve of a Nitroxide 'Spin Probe'
    • Improta, R.; Scalmani, G.; Barone, V. Quantum Mechanical Prediction of the Magnetic Titration Curve of a Nitroxide 'Spin Probe' Chem. Phys. Lett. 2001, 336, 349-356
    • (2001) Chem. Phys. Lett. , vol.336 , pp. 349-356
    • Improta, R.1    Scalmani, G.2    Barone, V.3
  • 28
    • 77955890954 scopus 로고    scopus 로고
    • A comparison of methods for measuring relative radical stabilities of carbon-centred radicals
    • Coote, M. L.; Lin, C. Y.; Beckwith, A. L. J.; Zavitsas, A. A. A comparison of methods for measuring relative radical stabilities of carbon-centred radicals Phys. Chem. Chem. Phys. 2010, 12, 9597-9610
    • (2010) Phys. Chem. Chem. Phys. , vol.12 , pp. 9597-9610
    • Coote, M.L.1    Lin, C.Y.2    Beckwith, A.L.J.3    Zavitsas, A.A.4
  • 29
    • 78650919019 scopus 로고    scopus 로고
    • The Radical Stabilization Energy of a Substituted Carbon-Centered Free Radical Depends on Both the Functionality of the Substituent and the Ordinality of the Radical
    • Poutsma, M. L. The Radical Stabilization Energy of a Substituted Carbon-Centered Free Radical Depends on Both the Functionality of the Substituent and the Ordinality of the Radical J. Org. Chem. 2011, 76, 270-276
    • (2011) J. Org. Chem. , vol.76 , pp. 270-276
    • Poutsma, M.L.1
  • 30
    • 84981760734 scopus 로고
    • Beziehungen Zwischen Konstitution und Katalytischer Aktivität von Thiolaminen Bei der Katalyse der Intramolekularen Cannizzaro-Reaktion
    • Franzen, V. Beziehungen Zwischen Konstitution und Katalytischer Aktivität von Thiolaminen Bei der Katalyse der Intramolekularen Cannizzaro-Reaktion Chem. Ber. 1957, 90, 623-633
    • (1957) Chem. Ber. , vol.90 , pp. 623-633
    • Franzen, V.1
  • 31
    • 28944445985 scopus 로고    scopus 로고
    • Steric and Polar Effects of the Cyclic Nitroxyl Fragment on the C-ON Bond Homolysis Rate Constant
    • Fischer, H.; Kramer, A.; Marque, S. R. A.; Nesvadba, P. Steric and Polar Effects of the Cyclic Nitroxyl Fragment on the C-ON Bond Homolysis Rate Constant Macromolecules 2005, 38, 9974-9984
    • (2005) Macromolecules , vol.38 , pp. 9974-9984
    • Fischer, H.1    Kramer, A.2    Marque, S.R.A.3    Nesvadba, P.4
  • 33
    • 0000745524 scopus 로고
    • Kinetics of Nitroxide Radical Trapping. 1. Solvent Effects
    • Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. Kinetics of Nitroxide Radical Trapping. 1. Solvent Effects J. Am. Chem. Soc. 1992, 114, 4983-4992
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4983-4992
    • Beckwith, A.L.J.1    Bowry, V.W.2    Ingold, K.U.3
  • 34
    • 0000745523 scopus 로고
    • Kinetics of Nitroxide Radical Trapping. 2. Structural Effects
    • Boury, V. W.; Ingold, K. U. Kinetics of Nitroxide Radical Trapping. 2. Structural Effects J. Am. Chem. Soc. 1992, 114, 4992-4997
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4992-4997
    • Boury, V.W.1    Ingold, K.U.2
  • 35
    • 33845280810 scopus 로고
    • Absolute Rate Constants for the Reactions of Some Carbon-Centered Radicals with 2,2,6,6-tetramethyl-1-piperidinoxyl
    • Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. Absolute Rate Constants for the Reactions of Some Carbon-Centered Radicals with 2,2,6,6-tetramethyl-1- piperidinoxyl J. Org. Chem. 1988, 53, 1629-1630
    • (1988) J. Org. Chem. , vol.53 , pp. 1629-1630
    • Chateauneuf, J.1    Lusztyk, J.2    Ingold, K.U.3
  • 36
    • 84900455704 scopus 로고    scopus 로고
    • Scavenging of Organic C-Centered Radicals by Nitroxides
    • 10.1021/cr4000946
    • Bagryanskaya, E. G.; Marque, S. R. A. Scavenging of Organic C-Centered Radicals by Nitroxides Chem. Rev. 2014, 10.1021/cr4000946
    • (2014) Chem. Rev.
    • Bagryanskaya, E.G.1    Marque, S.R.A.2
  • 37
  • 38
    • 70349974619 scopus 로고    scopus 로고
    • Theoretical Study of the Primary Processes in the Thermal Decomposition of Hydrazinium Nitroformate
    • Kiselev, V. G.; Gritsan, N. P. Theoretical Study of the Primary Processes in the Thermal Decomposition of Hydrazinium Nitroformate J. Phys. Chem. A 2009, 113, 11067-11074
    • (2009) J. Phys. Chem. A , vol.113 , pp. 11067-11074
    • Kiselev, V.G.1    Gritsan, N.P.2
  • 39
    • 79952270098 scopus 로고    scopus 로고
    • Tautomerism and Thermal Decomposition of Tetrazole: High-Level ab Initio Study
    • Kiselev, V. G.; Cheblakov, P. B.; Gritsan, N. P. Tautomerism and Thermal Decomposition of Tetrazole: High-Level ab Initio Study J. Phys. Chem. A 2011, 115, 1743-1753
    • (2011) J. Phys. Chem. A , vol.115 , pp. 1743-1753
    • Kiselev, V.G.1    Cheblakov, P.B.2    Gritsan, N.P.3
  • 40
    • 0035850379 scopus 로고    scopus 로고
    • Bond Dissociation Energies and Radical Stabilization Energies Associated with Substituted Methyl Radicals
    • Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. Bond Dissociation Energies and Radical Stabilization Energies Associated with Substituted Methyl Radicals J. Phys. Chem. A 2001, 105, 6750-6756
    • (2001) J. Phys. Chem. A , vol.105 , pp. 6750-6756
    • Henry, D.J.1    Parkinson, C.J.2    Mayer, P.M.3    Radom, L.4
  • 41
    • 77951173214 scopus 로고    scopus 로고
    • Linear Free-Energy Relationships for the Alkyl Radical Affinities of Nitroxides: A Theoretical Study
    • Hodgson, J. L.; Lin, C. Y.; Coote, M. L.; Marque, S. R. A.; Matyjaszewski, K. Linear Free-Energy Relationships for the Alkyl Radical Affinities of Nitroxides: A Theoretical Study Macromolecules 2010, 43, 3728-3743
    • (2010) Macromolecules , vol.43 , pp. 3728-3743
    • Hodgson, J.L.1    Lin, C.Y.2    Coote, M.L.3    Marque, S.R.A.4    Matyjaszewski, K.5
  • 42
    • 0000852156 scopus 로고
    • Are Relative Bond Energies a Measure of Radical Stabilization Energies?
    • Clark, K. B.; Wayner, D. D. M. Are Relative Bond Energies a Measure of Radical Stabilization Energies? J. Am. Chem. Soc. 1991, 113, 9363-9365
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9363-9365
    • Clark, K.B.1    Wayner, D.D.M.2
  • 43
    • 17444400483 scopus 로고    scopus 로고
    • Nitroxides with Two pK Values - Useful Spin Probes for pH Monitoring within a Broad Range
    • Kirilyuk, I. A.; Bobko, A. A.; Khramtsov, V. V.; Grigor'ev, I. A. Nitroxides with Two pK Values-Useful Spin Probes for pH Monitoring within a Broad Range Org. Biomol. Chem. 2005, 3, 1269-1274
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 1269-1274
    • Kirilyuk, I.A.1    Bobko, A.A.2    Khramtsov, V.V.3    Grigor'Ev, I.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.