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Volumn 68, Issue 16, 2003, Pages 6411-6423

Selectivity of purine alkylation by a quinone methide. Kinetic or thermodynamic control?

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILICITY;

EID: 0043076445     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0346252     Document Type: Article
Times cited : (47)

References (98)
  • 46
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    • A quantitative measure of nucleophilic character
    • Harris, J. M., McManus, S. P., Eds.; American Chemical Society: Washington, DC, Chapter 3
    • Lewis, E. D.; Douglas, T. A.; McLaughlin, M. L. A Quantitative Measure of Nucleophilic Character. In Nucleophilicity; Harris, J. M., McManus, S. P., Eds.; American Chemical Society: Washington, DC, 1987; Chapter 3, pp 35-49.
    • (1987) Nucleophilicity , pp. 35-49
    • Lewis, E.D.1    Douglas, T.A.2    McLaughlin, M.L.3
  • 49
    • 0042228128 scopus 로고    scopus 로고
    • note
    • For a comprehensive review of the use of molecular electrostatic potentials for the comparison and description of stable molecules see ref 18.
  • 83
    • 0041727750 scopus 로고    scopus 로고
    • note
    • -1 for ΔH‡ and ΔG‡ and +16.68 eu for ΔS‡.
  • 84
    • 84961985847 scopus 로고    scopus 로고
    • (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995. For the original COSMO model see: Klamt, A.; Schüürmann J. Chem. Soc., Perkins Trans. 1993, 2. Klamt, A.; Jonas, V.; Bürger, T.; Lohrenz, J. C. W. J. Phys. Chem. A 1998, 102, 5074. (b) For a more comprehensive treatment of solvation models see: (c) Cramer, C. J.; Truhlar, D. G. Chem Rev. 1999, 99, 2161.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 1995
    • Barone, V.1    Cossi, M.2
  • 85
    • 0242559868 scopus 로고
    • (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995. For the original COSMO model see: Klamt, A.; Schüürmann J. Chem. Soc., Perkins Trans. 1993, 2. Klamt, A.; Jonas, V.; Bürger, T.; Lohrenz, J. C. W. J. Phys. Chem. A 1998, 102, 5074. (b) For a more comprehensive treatment of solvation models see: (c) Cramer, C. J.; Truhlar, D. G. Chem Rev. 1999, 99, 2161.
    • (1993) J. Chem. Soc. Perkins Trans. , pp. 2
    • Klamt, A.1    Schüürmann2
  • 86
    • 4244072997 scopus 로고    scopus 로고
    • (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995. For the original COSMO model see: Klamt, A.; Schüürmann J. Chem. Soc., Perkins Trans. 1993, 2. Klamt, A.; Jonas, V.; Bürger, T.; Lohrenz, J. C. W. J. Phys. Chem. A 1998, 102, 5074. (b) For a more comprehensive treatment of solvation models see: (c) Cramer, C. J.; Truhlar, D. G. Chem Rev. 1999, 99, 2161.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 5074
    • Klamt, A.1    Jonas, V.2    Bürger, T.3    Lohrenz, J.C.W.4
  • 87
    • 84961981091 scopus 로고    scopus 로고
    • (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995. For the original COSMO model see: Klamt, A.; Schüürmann J. Chem. Soc., Perkins Trans. 1993, 2. Klamt, A.; Jonas, V.; Bürger, T.; Lohrenz, J. C. W. J. Phys. Chem. A 1998, 102, 5074. (b) For a more comprehensive treatment of solvation models see: (c) Cramer, C. J.; Truhlar, D. G. Chem Rev. 1999, 99, 2161.
    • (1999) Chem Rev. , vol.99 , pp. 2161
    • Cramer, C.J.1    Truhlar, D.G.2
  • 92
    • 0043230260 scopus 로고    scopus 로고
    • note
    • We have neglected those tautomers of G and G-adduct,involving N9 hydrogen atom because in a prototype model of dG that proton is replaced by an alkyl substituent.
  • 93
    • 0042228125 scopus 로고    scopus 로고
    • note
    • We are currently investigating the role of the bulk effect of acetonitrile and DMSO on the barriers and on adduct stability, because they show dielectric constants very similar to that assumed for the interior of a nucleic acid double helix (ref 28d).
  • 95
    • 0043230259 scopus 로고    scopus 로고
    • note
    • -1, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.