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Volumn 47, Issue 3, 2008, Pages 632-637

Solvent effects on the kinetics of a diels-alder reaction in gas-expanded liquids

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTION; GAS-EXPANDED LIQUID (GXL); MULTIPARAMETER APPROACH;

EID: 39449137545     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie070618i     Document Type: Article
Times cited : (24)

References (48)
  • 2
    • 2442551734 scopus 로고    scopus 로고
    • Molecular insight, through IR spectroscopy, on solvating phenomena occurring in C02-expanded solutions
    • Sala, S.; Tassaing, T.; Ventosa, N.; Danten, Y.; Besnard, M.; Veciana, J. Molecular insight, through IR spectroscopy, on solvating phenomena occurring in C02-expanded solutions. ChemPhysChem 2004, 5, 243.
    • (2004) ChemPhysChem , vol.5 , pp. 243
    • Sala, S.1    Tassaing, T.2    Ventosa, N.3    Danten, Y.4    Besnard, M.5    Veciana, J.6
  • 3
    • 0037139462 scopus 로고    scopus 로고
    • 2expanded solvents: Unique and versatile media for performing homogeneous catalytic oxidations
    • 2expanded solvents: unique and versatile media for performing homogeneous catalytic oxidations. J. Am. Chem. Soc. 2002, 124 (11), 2513.
    • (2002) J. Am. Chem. Soc , vol.124 , Issue.11 , pp. 2513
    • Wei, M.1    Musie, G.T.2    Busch, D.H.3    Subramaniam, B.4
  • 6
    • 33644796101 scopus 로고    scopus 로고
    • Photoresist and residue removal using gas-expanded liquids
    • Song, I.; Spuller, M.; Levitin, G.; Hess, D. W. Photoresist and residue removal using gas-expanded liquids. J. Electrochem. Soc. 2006, 153 (4), G314.
    • (2006) J. Electrochem. Soc , vol.153 , Issue.4
    • Song, I.1    Spuller, M.2    Levitin, G.3    Hess, D.W.4
  • 10
    • 24944515329 scopus 로고    scopus 로고
    • Determination of solvatochromic solvent parameters for the characterization of gas-expanded liquids
    • Wyatt, V. T.; Bush, D.; Lu, J.; Hallett, J. P.; Liotta, C. L.; Eckert, C A. Determination of solvatochromic solvent parameters for the characterization of gas-expanded liquids. J. Supercrit. Fluids 2005, 36, 16.
    • (2005) J. Supercrit. Fluids , vol.36 , pp. 16
    • Wyatt, V.T.1    Bush, D.2    Lu, J.3    Hallett, J.P.4    Liotta, C.L.5    Eckert, C.A.6
  • 12
    • 0023439314 scopus 로고
    • Clustering in supercritical fluid mixtures
    • Kim, S.; Johnston, K. P. Clustering in supercritical fluid mixtures. AIChE J. 1987, 33 (10), 1603.
    • (1987) AIChE J , vol.33 , Issue.10 , pp. 1603
    • Kim, S.1    Johnston, K.P.2
  • 13
    • 0029659151 scopus 로고    scopus 로고
    • Supercritical fluids as solvents for chemical and materials processing
    • Eckert, C. A.; Knutson, B. L.; Debenedetti, P. G. Supercritical fluids as solvents for chemical and materials processing. Nature 1996, 383, 313.
    • (1996) Nature , vol.383 , pp. 313
    • Eckert, C.A.1    Knutson, B.L.2    Debenedetti, P.G.3
  • 14
    • 0002470521 scopus 로고
    • Local density augmentation in supercritical solutions. A comparison between fluorescence spectroscopy and molecular dynamics results
    • Supercritical Fluid Technology; Bright, F. V, McNally, M. E. P, Eds, American Chemical Society: Washington, DC
    • Knutson, B. L.; Tomasko, D. L.; Eckert, C. A.; Debenedetti, P. G.; Chialvo, A. A. Local density augmentation in supercritical solutions. A comparison between fluorescence spectroscopy and molecular dynamics results. In Supercritical Fluid Technology; Bright, F. V., McNally, M. E. P., Eds.; ACS Symposium Series 488; American Chemical Society: Washington, DC, 1992; pp 60-72.
    • (1992) ACS Symposium Series , vol.488 , pp. 60-72
    • Knutson, B.L.1    Tomasko, D.L.2    Eckert, C.A.3    Debenedetti, P.G.4    Chialvo, A.A.5
  • 15
    • 0027623731 scopus 로고
    • Chemical-Physical Interpretation of Cosolvent Effects in Supercritical Fluids
    • Ting, S. S. T.; Tomasko, D. L.; Macnaughton, S. J.; Foster, N. R. Chemical-Physical Interpretation of Cosolvent Effects in Supercritical Fluids. Ind. Eng. Chem. Res. 1993, 32, 1482.
    • (1993) Ind. Eng. Chem. Res , vol.32 , pp. 1482
    • Ting, S.S.T.1    Tomasko, D.L.2    Macnaughton, S.J.3    Foster, N.R.4
  • 16
    • 0039726458 scopus 로고
    • The solvatochromic comparison method. 6. The π* scale of solvent polarities
    • Kamlet, M. J.; Abboud, J. L.; Taft, R. W. The solvatochromic comparison method. 6. The π* scale of solvent polarities. J. Am. Chem. Soc. 1977, 99 (18), 6027.
    • (1977) J. Am. Chem. Soc , vol.99 , Issue.18 , pp. 6027
    • Kamlet, M.J.1    Abboud, J.L.2    Taft, R.W.3
  • 17
    • 0006469110 scopus 로고
    • The properties of organic liquids that are relevant to their use as solvating solvents
    • Marcus, Y. The properties of organic liquids that are relevant to their use as solvating solvents. Chem. Soc. Rev. 1993, 409.
    • (1993) Chem. Soc. Rev , pp. 409
    • Marcus, Y.1
  • 18
    • 33847797571 scopus 로고
    • The solvatochromic comparison method. 2. The a-scale of solvent hydrogen-bond donor (HBD) acidities
    • Taft, R. W.; Kamlet, M. J. The solvatochromic comparison method. 2. The a-scale of solvent hydrogen-bond donor (HBD) acidities. J. Am. Chem. Soc. 1976, 95 (10), 2886.
    • (1976) J. Am. Chem. Soc , vol.95 , Issue.10 , pp. 2886
    • Taft, R.W.1    Kamlet, M.J.2
  • 19
    • 37049079068 scopus 로고
    • Polarity and basicity of solvents Part 2. Solvatochromic hydrogen-bonding shifts as basicity parameters
    • Laurence, C.; Nicolet, P.; Helbert, M. Polarity and basicity of solvents Part 2. Solvatochromic hydrogen-bonding shifts as basicity parameters. J. Chem. Soc., Perkin Trans. 2 1986, 1081.
    • (1986) J. Chem. Soc., Perkin Trans. 2 , pp. 1081
    • Laurence, C.1    Nicolet, P.2    Helbert, M.3
  • 20
    • 37049086534 scopus 로고
    • Polarity and basicity of solvents. Part 1. A thermosolvatochromic comparison method
    • Nicolet, P.; Laurence, C. Polarity and basicity of solvents. Part 1. A thermosolvatochromic comparison method. J. Chem. Soc., Perkin Trans. 2 1986, 1071.
    • (1986) J. Chem. Soc., Perkin Trans. 2 , pp. 1071
    • Nicolet, P.1    Laurence, C.2
  • 21
    • 33847800055 scopus 로고
    • The solvatochromic comparison method. I. The β-scale of solvent hydrogen-bond acceptor (HBA) basicities
    • Kamlet, M. J.; Taft, R. W. The solvatochromic comparison method. I. The β-scale of solvent hydrogen-bond acceptor (HBA) basicities. J. Am. Chem. Soc. 1976, 95 (2), 377.
    • (1976) J. Am. Chem. Soc , vol.95 , Issue.2 , pp. 377
    • Kamlet, M.J.1    Taft, R.W.2
  • 23
    • 0037066996 scopus 로고    scopus 로고
    • Solvatochromic characterization of near-critical water as a benign reaction medium
    • Lu, J.; Brown, J. S.; Boughner, E. C.; Liotta, C. L.; Eckert, C. A. Solvatochromic characterization of near-critical water as a benign reaction medium. Ind. Eng. Chem. Res. 2002, 41, 2835.
    • (2002) Ind. Eng. Chem. Res , vol.41 , pp. 2835
    • Lu, J.1    Brown, J.S.2    Boughner, E.C.3    Liotta, C.L.4    Eckert, C.A.5
  • 24
    • 5844252510 scopus 로고
    • Solvatochromic dyes as solvent polarity indicators
    • Reichardt, C. Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 1994, 94, 2319.
    • (1994) Chem. Rev , vol.94 , pp. 2319
    • Reichardt, C.1
  • 25
    • 0038728510 scopus 로고    scopus 로고
    • Spectroscopically probing microscopic solvent properties of room-temperature ionic liquids with the addition of carbon dioxide
    • Lu, J.; Liotta, C. L.; Eckert, C. A. Spectroscopically probing microscopic solvent properties of room-temperature ionic liquids with the addition of carbon dioxide. J. Phys. Chem. A 2003, 107, 3995.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 3995
    • Lu, J.1    Liotta, C.L.2    Eckert, C.A.3
  • 26
    • 0001005256 scopus 로고
    • Supercritical carbon dioxide: Behavior of π* and β solvatochromic indicators in media of different densities
    • Sigman, M. E.; Lindley, S. M.; Leffler, J. E. Supercritical carbon dioxide: Behavior of π* and β solvatochromic indicators in media of different densities. J. Am. Chem. Soc. 1985, 1 07, 1471.
    • (1985) J. Am. Chem. Soc , vol.1 , Issue.7 , pp. 1471
    • Sigman, M.E.1    Lindley, S.M.2    Leffler, J.E.3
  • 27
    • 0000307251 scopus 로고    scopus 로고
    • Solvatochromism in pure and binary solvent mixtures: Effects of the molecular structure of the zwitterionic probe
    • Tada, E. B.; Novaki, L. P.; El Seoud, O. A. Solvatochromism in pure and binary solvent mixtures: effects of the molecular structure of the zwitterionic probe. J. Phys. Org. Chem. 2000, 13, 679.
    • (2000) J. Phys. Org. Chem , vol.13 , pp. 679
    • Tada, E.B.1    Novaki, L.P.2    El Seoud, O.A.3
  • 28
    • 0347833126 scopus 로고
    • Study of solvation effects in Diels-Alder reactions of 4-phenyl-1,2,4-triazoline3,5-dione with anthracene and trans,trans-1,4-diphenyl-,3-butadiene
    • Konovalov, A. I.; Breus, I. P.; Sharagin, I. A.; Kiselev, V. D. Study of solvation effects in Diels-Alder reactions of 4-phenyl-1,2,4-triazoline3,5-dione with anthracene and trans,trans-1,4-diphenyl-,3-butadiene. Zh. Org. Khim. 1979, 15 (2), 361.
    • (1979) Zh. Org. Khim , vol.15 , Issue.2 , pp. 361
    • Konovalov, A.I.1    Breus, I.P.2    Sharagin, I.A.3    Kiselev, V.D.4
  • 31
    • 0001094537 scopus 로고    scopus 로고
    • Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. 4-Phenyl-1,2,4- triazolin-3,5-dione: A powerful dienophile. Tetrahedron Lett. 1962, 14, 615.
    • Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. 4-Phenyl-1,2,4- triazolin-3,5-dione: A powerful dienophile. Tetrahedron Lett. 1962, 14, 615.
  • 32
    • 37049110748 scopus 로고
    • Duality of pathways in the reaction of N-phenyltriazolinedione with alcohols
    • Dao, L. H.; Mackay, D. Duality of pathways in the reaction of N-phenyltriazolinedione with alcohols. J. Chem. Soc., Chem. Commun. 1976, 326.
    • (1976) J. Chem. Soc., Chem. Commun , pp. 326
    • Dao, L.H.1    Mackay, D.2
  • 33
    • 0003620156 scopus 로고
    • Decomposition reactions of a cis-diacyl diimide. 4-Phenyl-l,2,4-triazoline-3,5-dione
    • Izydore, R. A.; Johnson, H. E.; Horton, R. T. Decomposition reactions of a cis-diacyl diimide. 4-Phenyl-l,2,4-triazoline-3,5-dione. J. Org. Chem. 1985, 50, 4589.
    • (1985) J. Org. Chem , vol.50 , pp. 4589
    • Izydore, R.A.1    Johnson, H.E.2    Horton, R.T.3
  • 35
    • 0035820404 scopus 로고    scopus 로고
    • Polarity and hydrogen-bonding of ambient to near-critical water: Kamlet-Taft solvent parameters
    • Lu, J.; Brown, J. S.; Liotta, C. L.; Eckert, C. A. Polarity and hydrogen-bonding of ambient to near-critical water: Kamlet-Taft solvent parameters. Chem. Commun. 2001, 665.
    • (2001) Chem. Commun , pp. 665
    • Lu, J.1    Brown, J.S.2    Liotta, C.L.3    Eckert, C.A.4
  • 36
    • 12344273560 scopus 로고    scopus 로고
    • Highpressure vapor-liquid equilbria of some carbondioxide + organic binary systems
    • Lazzaroni, M. J.; Bush, D.; Brown, J. S.; Eckert, C. A. Highpressure vapor-liquid equilbria of some carbon"dioxide + organic binary systems. J. Chem. Eng. Data 2005, 50, 60.
    • (2005) J. Chem. Eng. Data , vol.50 , pp. 60
    • Lazzaroni, M.J.1    Bush, D.2    Brown, J.S.3    Eckert, C.A.4
  • 37
    • 3242836480 scopus 로고
    • Liquid and Supercritical Carbon Dioxide as Organic Solvents
    • »Hyatt, J. A. Liquid and Supercritical Carbon Dioxide as Organic Solvents. J. Org. Chem. 1984, 49, 5097.
    • (1984) J. Org. Chem , vol.49 , pp. 5097
    • »Hyatt, J.A.1
  • 38
    • 0033626942 scopus 로고    scopus 로고
    • Kamlet-Taft solvatochromic parameters of eight alkanolamines
    • Lagalante, A. F.; Spadi, M.; Bruno, T. J. Kamlet-Taft solvatochromic parameters of eight alkanolamines. J. Chem. Eng. Data 2000,45, 382.
    • (2000) J. Chem. Eng. Data , vol.45 , pp. 382
    • Lagalante, A.F.1    Spadi, M.2    Bruno, T.J.3
  • 39
    • 0009220838 scopus 로고    scopus 로고
    • Investigation of the CH3CN-CO2 potential energy surface using symmetry-adapted perturbation theory
    • Williams, H. L.; Rice, B. M.; Chabalowski, C. F. Investigation of the CH3CN-CO2 potential energy surface using symmetry-adapted perturbation theory. J. Phys. Chem. A 1998, 102, 6981.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 6981
    • Williams, H.L.1    Rice, B.M.2    Chabalowski, C.F.3
  • 41
    • 5844297139 scopus 로고
    • High-pressure kinetic studies of solvent and substituent effects on Diels-Alder reactions
    • McCabe, J. R.; Eckert, C. A. High-pressure kinetic studies of solvent and substituent effects on Diels-Alder reactions. Ind. Eng. Chem. Fundam. 1974, 13 (3), 168.
    • (1974) Ind. Eng. Chem. Fundam , vol.13 , Issue.3 , pp. 168
    • McCabe, J.R.1    Eckert, C.A.2
  • 43
    • 0142196137 scopus 로고    scopus 로고
    • Diels-Alder reactions of anthracene, 9-substituted anthracenes and 9, 10-disubstituted anthracenes
    • Atherton, J. C. C.; Jones, S. Diels-Alder reactions of anthracene, 9-substituted anthracenes and 9, 10-disubstituted anthracenes. Tetrahedron 2003, 59, 9039.
    • (2003) Tetrahedron , vol.59 , pp. 9039
    • Atherton, J.C.C.1    Jones, S.2
  • 46
    • 0034614050 scopus 로고    scopus 로고
    • Fluorophobic acceleration of Diels-Alder reactions
    • Myers, K. E.; Kumar, K. Fluorophobic acceleration of Diels-Alder reactions. J. Am. Chem. Soc. 2000, 122, 12025.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 12025
    • Myers, K.E.1    Kumar, K.2
  • 47
    • 33847085398 scopus 로고
    • Hydrophobic acceleration of DielsAlder reactions
    • Rideout, D. C.; Breslow, R. Hydrophobic acceleration of DielsAlder reactions. J. Am. Chem. Soc. 1980, 102, 7816.
    • (1980) J. Am. Chem. Soc , vol.102 , pp. 7816
    • Rideout, D.C.1    Breslow, R.2


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