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Volumn 64, Issue 8, 1999, Pages 2626-2629

Electron-transfer nucleophilic substitution reactions on neopentyl- and phenyl-substituted alkyl chlorides. Effect of the bridge length on the intramolecular electron-transfer catalysis

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; ANION; BIPHENYL; CHLORIDE; METHYL GROUP; PENTANE; PHENYL GROUP; PHOSPHINE DERIVATIVE; RADICAL;

EID: 0033574389     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980657r     Document Type: Article
Times cited : (22)

References (50)
  • 1
    • 0003467672 scopus 로고
    • John Wiley & Sons: New York
    • March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1990, Part A.
    • (1992) Advanced Organic Chemistry, 4th Ed.
    • March, J.1
  • 2
    • 85022827076 scopus 로고
    • Plenum Press: New York
    • March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1990, Part A.
    • (1990) Advanced Organic Chemistry, 3rd Ed. , Issue.PART A
    • Carey, F.A.1    Sundberg, R.J.2
  • 4
    • 0345570372 scopus 로고
    • RN1, see: (a) Rossi, R. A.; Pierini, A. B.; Palacios, S. M. Advances in Free Radical Chemistry; Tanner, D. D., Ed.; JAI Press: Greenwich, CT, 1990; p 193; J. Chem. Educ. 1989, 66, 720.
    • (1989) J. Chem. Educ. , vol.66 , pp. 720
  • 20
    • 37049134760 scopus 로고
    • Experimental and theoretical data have been used to support the existence of π and σ radical anions. See: (a) Clarke, D. D.; Coulson, C. A. J. Chem. Soc. A 1969, 169.
    • (1969) J. Chem. Soc. A , pp. 169
    • Clarke, D.D.1    Coulson, C.A.2
  • 29
    • 0004104553 scopus 로고
    • Springer-Verlag: Berlin
    • (d) Kuki, A. Structure and Bonding; Springer-Verlag: Berlin, 1991; p 50.
    • (1991) Structure and Bonding , pp. 50
    • Kuki, A.1
  • 33
    • 0002772114 scopus 로고
    • Lewis, E. S., Ed.; Wiley-Interscience: New York
    • t are concentration at time t of both substrates. This equation is based on a first-order reaction of both substrates with the nucleophile. See: Bunnett, J. F. In Investigation of Rates and Mechanisms of Reaction, 3rd ed.; Lewis, E. S., Ed.; Wiley-Interscience: New York, 1974; part 1, p 159.
    • (1974) Investigation of Rates and Mechanisms of Reaction, 3rd Ed. , Issue.1 PART , pp. 159
    • Bunnett, J.F.1
  • 34
    • 0000682727 scopus 로고
    • AMPAC version 2.1, Quantum Chemistry Program Exchange program 506
    • All the calculations were carried out with complete geometry optimization, and the semiempirical AM1 method as implemented in AMPAC. See: Liotard, D. A.; Healy, E. F.; Ruiz, J. M.; Dewar, M. J. S. AMPAC version 2.1, Quantum Chemistry Program Exchange program 506. QCPE Bull. 1989, 9, 123.
    • (1989) QCPE Bull. , vol.9 , pp. 123
    • Liotard, D.A.1    Healy, E.F.2    Ruiz, J.M.3    Dewar, M.J.S.4
  • 36
    • 0345070458 scopus 로고    scopus 로고
    • note
    • (a) The AM1/UHF stationary points were characterized by calculating their Hessian matrix, no negative eigenvalue for a minimun energy structure, and one negative eigenvalue for a transition state. (b) The CI calculations were performed with the AM1/RHF Hamiltonian within the subspace of all possible excitations of five electrons into five molecular orbitals, from SOMO-2 up to SOMO+2 (CI = 5).
  • 43
    • 0010954502 scopus 로고    scopus 로고
    • 9 at 298 K. See: Formosinho, S. J.; Arnaut, L. G. Bull. Chem. Soc. Jpn. 1997, 70, 977. For exchange reaction of other aromatic radical anions, see: Ward, R. L.; Weissman, S. I. J. Am. Chem. Soc. 1954, 76, 3612. Bergman, I. Trans. Faraday Soc. 1954, 50, 829.
    • (1997) Bull. Chem. Soc. Jpn. , vol.70 , pp. 977
    • Formosinho, S.J.1    Arnaut, L.G.2
  • 44
    • 0041149487 scopus 로고
    • 9 at 298 K. See: Formosinho, S. J.; Arnaut, L. G. Bull. Chem. Soc. Jpn. 1997, 70, 977. For exchange reaction of other aromatic radical anions, see: Ward, R. L.; Weissman, S. I. J. Am. Chem. Soc. 1954, 76, 3612. Bergman, I. Trans. Faraday Soc. 1954, 50, 829.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 3612
    • Ward, R.L.1    Weissman, S.I.2
  • 45
    • 0000178819 scopus 로고
    • 9 at 298 K. See: Formosinho, S. J.; Arnaut, L. G. Bull. Chem. Soc. Jpn. 1997, 70, 977. For exchange reaction of other aromatic radical anions, see: Ward, R. L.; Weissman, S. I. J. Am. Chem. Soc. 1954, 76, 3612. Bergman, I. Trans. Faraday Soc. 1954, 50, 829.
    • (1954) Trans. Faraday Soc. , vol.50 , pp. 829
    • Bergman, I.1
  • 46
    • 0004255572 scopus 로고    scopus 로고
    • International Business Machines Corporation, We were unable to reach this limit experimentally
    • 5b, ≅ 1 under high dilution, conditions where the equilibrium is not attained, according to simulations performed with the program Chemical Kinetics Simulator 1.01 (International Business Machines Corporation, 1996). We were unable to reach this limit experimentally.
    • (1996) Chemical Kinetics Simulator 1.01
  • 47
    • 0344208297 scopus 로고    scopus 로고
    • note
    • t)
  • 49


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