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Volumn 126, Issue 49, 2004, Pages 16051-16057

Fragmentation of aryl halide π anion radicals. Bending of the cleaving bond and activation vs driving force relationships

Author keywords

[No Author keywords available]

Indexed keywords

BENDING (DEFORMATION); CHEMICAL BONDS; CORRELATION METHODS; CYCLIC VOLTAMMETRY; MATHEMATICAL MODELS; NEGATIVE IONS; REACTION KINETICS;

EID: 10344238110     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045989u     Document Type: Article
Times cited : (150)

References (79)
  • 1
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    • References 1b - 1e and references therein
    • (a) References 1b - 1e and references therein.
  • 3
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    • Single Electron Transfer and Nucleophilic Substitution
    • Bethel, D., Ed.; Academic Press: New York
    • (c) Savéant, J.-M. Single Electron Transfer and Nucleophilic Substitution. In. Advances in Physical Organic Chemistry; Bethel, D., Ed.; Academic Press: New York, 1990, vol. 26, pp 1-130.
    • (1990) Advances in Physical Organic Chemistry , vol.26 , pp. 1-130
    • Savéant, J.-M.1
  • 4
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    • Electron Transfer, Bond Breaking and Bond Formation
    • Tidwell, T. T., Ed.; Academic Press: New York
    • (d) Savéant, J.-M. Electron Transfer, Bond Breaking and Bond Formation. In Advances in Physical Organic Chemistry; Tidwell, T. T., Ed.; Academic Press: New York, 2000, Vol. 35, pp 117-192.
    • (2000) Advances in Physical Organic Chemistry , vol.35 , pp. 117-192
    • Savéant, J.-M.1
  • 6
    • 10344239373 scopus 로고    scopus 로고
    • note
    • (a) Exceptions are the electrochemical reductions of iodobenzene and 4-methyliodobenzene where the mechanism shifts from concerted to stepwise upon increasing the driving force.
  • 14
    • 10344252754 scopus 로고    scopus 로고
    • note
    • -1.
  • 25
    • 10344253261 scopus 로고    scopus 로고
    • note
    • (l) the structure of 5-bromo-8-methoxypsoralen studied in ref 4k is as follows: (Equation Presented)
  • 31
    • 10344242906 scopus 로고    scopus 로고
    • note
    • 5b-e
  • 36
    • 10344230398 scopus 로고    scopus 로고
    • note
    • 5g of the redox catalysis approach, using steady-state techniques or optical detection instead of cyclic voltammetry, reports the possibility to reach somewhat higher rate constants.
  • 38
    • 10344254793 scopus 로고    scopus 로고
    • note
    • RN1 substitution, key references are the following.
  • 49
    • 10344248140 scopus 로고    scopus 로고
    • note
    • [Ar•]•-) may be considered as compensating each other.
  • 50
    • 0001796419 scopus 로고
    • Theory and Applications of Electron Transfers at Electrodes and in Solution
    • Rock, P. A., Ed.; Elsevier: New York
    • Marcus, R. A. Theory and Applications of Electron Transfers at Electrodes and in Solution. In Special Topics in Electrochemistry; Rock, P. A., Ed.; Elsevier: New York, 1977; pp 161-179.
    • (1977) Special Topics in Electrochemistry , pp. 161-179
    • Marcus, R.A.1
  • 56
    • 10344257989 scopus 로고    scopus 로고
    • note
    • (a) Besides the case of 4-cyano-chlorobenzene, treated in details in ref 12, an indication that bond bending effects may play an important role is given in ref 11, where it is shown on the base of DFT calculations that the transition states are more bended than the initial state and that the activation energy calculated with no geometrical constraint is smaller than the activation energy with forced planarity (corresponding to a conical intersection). However, the comparison seems uncertain, if not inaccurate, since a single reference method was used in these calculations (B3LYP), as strongly emphasized in many cases when conical intersections are involved (see, for example, refs 14b-d).
  • 60
  • 66
    • 10344260631 scopus 로고    scopus 로고
    • note
    • -6, i.e., is very much in favor of the ECE pathway, for an interval of scan rates, υ, ranging from 0.1 to 10000 V/s.
  • 67
    • 10344248139 scopus 로고    scopus 로고
    • note
    • 0) + 0.44. Free enthlapies of transfer from water to DMF for the various ions were obtained from ref 15, while standard free enthalpies of formation for chlorine, bromine, chloride and bromide were collected from ref 19b.
  • 70
    • 10344232628 scopus 로고    scopus 로고
    • note
    • The same remark also applies to Figure 7 in ref 5g.
  • 72
    • 2142647834 scopus 로고    scopus 로고
    • Fry, A. J., Matsumura, A., Eds.; The Electrochemical Society, Inc.: New Jersey
    • (a) Cardinale, A.; Gennaro, A.; Isse, A. A.; Maran, F. In New Directions in Organic Electrochemistry; Fry, A. J., Matsumura, A., Eds.; The Electrochemical Society, Inc.: New Jersey, 2000; Vol. 200-15, pp 136-140.
    • (2000) New Directions in Organic Electrochemistry , vol.200 , Issue.15 , pp. 136-140
    • Cardinale, A.1    Gennaro, A.2    Isse, A.A.3    Maran, F.4
  • 76
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    • note
    • 12b


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.