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Volumn 72, Issue 18, 2007, Pages 6970-6981

Bonded exciplexes. A new concept in photochemical reactions

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; CHARGE TRANSFER; EXCITED STATES; FREE ENERGY; PYRIDINE; QUENCHING; RATE CONSTANTS;

EID: 34548730201     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071157d     Document Type: Article
Times cited : (69)

References (92)
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    • See, for example: a, Padwa, A, Ed, Dekker: New York
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    • (c) Evans, T. R.; Wake, R. W.; Jaenicke, O. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic Press: New York, 1975; p 345.
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    • With the exception of toluene, the oxidation potentials for the alkylbenzenes used to calculated the reaction exothermicities were taken from ref 8a. The oxidation potential of toluene was estimated to be 2.33 V versus SCE based on measurements in trifluoroacetic acid.12b,c In trifluoroacetic acid, the reported oxidation potentials of the other alkylbenzenes, when referenced versus SCE, are on average ∼0.02 V higher than those in ref 8a
    • 12b,c In trifluoroacetic acid, the reported oxidation potentials of the other alkylbenzenes, when referenced versus SCE, are on average ∼0.02 V higher than those in ref 8a.
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    • The negatively charged counterion may contribute to stabilization in less polar solvents than acetonitrile where ion pairing may be significant. 13b
    • 13b
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    • The rate constants for quenching of some excited pyrylium salts were also reported by Jacques et al.6d
    • 6d
  • 54
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    • Exciplex emission spectra in acetonitrile have now been reported for a number of systems; see, for example, refs 4a, 11d, and: (a) Gould, I. R.; Young, R. H.; Mueller, L. J.; Farid, S. J. Am. Chem. Soc. 1994, 116, 8176.
    • Exciplex emission spectra in acetonitrile have now been reported for a number of systems; see, for example, refs 4a, 11d, and: (a) Gould, I. R.; Young, R. H.; Mueller, L. J.; Farid, S. J. Am. Chem. Soc. 1994, 116, 8176.
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    • For more detailed discussions of the analysis of the bandwidths of such exciplex spectra, the derivation of reduced spectra from measured spectra, and the determination of ion pair energies from such spectra, see ref 11e. The similarity in the reorganization energies for these systems contrasts with that found for corresponding emissions of the smaller electron acceptor tetracyanobenzene with various alkylbenzene donors, where a decrease in reorganization energy with increasing substitution (and thus size) of the donor could be detected.11e
    • 11e
  • 61
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    • Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Ion Energetics Data in NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; June 2005, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov).
    • Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. "Ion Energetics Data" in NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; June 2005, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov).
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    • For a literature summary regarding the assignment of the lowest ionic state of pyridine, see
    • For a literature summary regarding the assignment of the lowest ionic state of pyridine, see: Tsubouchi, M.; Suzuki, T. J. Phys. Chem. A 2003, 107, 10897.
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    • Tsubouchi, M.1    Suzuki, T.2
  • 66
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    • New Theoretical Concepts for Understanding Organic Reactions
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    • (d) Shaik, S. S. In New Theoretical Concepts for Understanding Organic Reactions; Bertrán, J., Csizmadia, I. G., Eds.; NATO ASI Series; Kluwer: Dordrecht, The Netherlands, 1989; Vol. C267, p 165.
    • (1989) NATO ASI Series , vol.C267 , pp. 165
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  • 68
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    • For leading references to the use of similar curve-crossing models, see: a
    • For leading references to the use of similar curve-crossing models, see: (a) Michl, J. Phys. Chem. 1975, 7, 125.
    • (1975) Phys. Chem , vol.7 , pp. 125
    • Michl, J.1
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    • For some references to recent applications of similar models, see: c
    • For some references to recent applications of similar models, see: (c) Burghardt, I.; Laage, D.; Hynes, James, T. J. Phys. Chem. A 2003, 107, 11292.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 11292
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    • Jaguar, version 6.5 build 112, Schrödinger Inc, Portland, OR
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    • For comparison, the C-N bond dissociation energies of the N-methylpyridinium and N-cyanomethylpyridinium cations calculated at the B3LYP/6-31G* level of theory are 111 and 84 kcal/mol, respectively.
    • For comparison, the C-N bond dissociation energies of the N-methylpyridinium and N-cyanomethylpyridinium cations calculated at the B3LYP/6-31G* level of theory are 111 and 84 kcal/mol, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.