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Volumn 122, Issue 30, 2000, Pages 7342-7350

Using incoming nucleophile primary hydrogen - deuterium kinetic isotope effects to model the S(N)2 transition state

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL CHLORIDE; BORANE DERIVATIVE; DEUTERIUM; HYDROGEN; ISOTOPE;

EID: 0034596288     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000441i     Document Type: Article
Times cited : (16)

References (76)
  • 6
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    • Shiner, V. J., Jr.; Wilgis, F. P. In Isotopes in organic chemistry; Buncel, E., Saunders, W. H., Jr., Eds.; Elsevier Science Publishing Co. Inc.: New York, 1992; Vol. 8, pp 289-292, 303-305.
    • (1992) Isotopes in Organic Chemistry , vol.8 , pp. 289-292
    • Shiner V.J., Jr.1    Wilgis, F.P.2
  • 18
    • 0343169865 scopus 로고    scopus 로고
    • note
    • 15 agree (within 10%) with those found in this study. Given the difficulty in reproducing rate constants in different batches of DMSO and the small temperature difference between the two studies, the results of the two studies are in reasonable agreement.
  • 32
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    • Cambridge University Press: London.
    • Johnson, C. D. In The Hammett Equation; Cambridge University Press: London. 1973; pp 1-50.
    • (1973) The Hammett Equation , pp. 1-50
    • Johnson, C.D.1
  • 37
    • 0342300323 scopus 로고    scopus 로고
    • Deleted in proof
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    • Ph.D. Dissertation, University of Wisconsin, Madison, WI
    • Grimsrud, E. P. Ph.D. Dissertation, University of Wisconsin, Madison, WI, 1971.
    • (1971)
    • Grimsrud, E.P.1
  • 41
    • 0342300324 scopus 로고    scopus 로고
    • Deleted in proof
    • Deleted in proof.
  • 47
    • 0041020201 scopus 로고
    • Collins, C. J., Bowman, N. S., Eds.; ACS Publication 167; Van Nostrand Rheinhold: New York
    • Shiner, V. J., Jr. In Isotope Effects in Chemical Reactions; Collins, C. J., Bowman, N. S., Eds.; ACS Publication 167; Van Nostrand Rheinhold: New York, 1970; pp 90-159.
    • (1970) Isotope Effects in Chemical Reactions , pp. 90-159
    • Shiner V.J., Jr.1
  • 49
    • 0342300321 scopus 로고
    • Buncel, E., Lee, C. C., Eds.; Elsevier Science Publishing Co. Inc.: New York
    • Westaway, K. C. In Isotopes in organic chemistry: Buncel, E., Lee, C. C., Eds.; Elsevier Science Publishing Co. Inc.: New York, 1987; p 312.
    • (1987) Isotopes in Organic Chemistry , pp. 312
    • Westaway, K.C.1
  • 53
    • 0342735366 scopus 로고
    • Buncel, E., Lee, C. C., Eds.; Elsevier Science Publishing Co. Inc.: New York
    • Westaway, K. C. In Isotopes in organic chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier Science Publishing Co. Inc.: New York, 1987; pp 313-319.
    • (1987) Isotopes in Organic Chemistry , pp. 313-319
    • Westaway, K.C.1
  • 58
    • 0343169859 scopus 로고    scopus 로고
    • note
    • Theoretical calculations by Saunders and co-workers (Table 2, ref 45) have shown that the contribution of heavy atom motion to the reaction coordinate motion is more pronounced in unsymmetric transition states. Heavy atom motion increases the effective mass of the transferring hydride ion and reduces the probability of tunnelling.
  • 62
    • 0038570245 scopus 로고
    • Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, MD
    • Kirsch, J. F. In Isotope effects on enzyme catalyzed reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, MD. 1977; p 18.
    • (1977) Isotope Effects on Enzyme Catalyzed Reactions , pp. 18
    • Kirsch, J.F.1
  • 65
    • 0343169858 scopus 로고    scopus 로고
    • note
    • α-Cl bonds are long in all the transition states, except perhaps the reaction with p-nitrobenzyl chloride (vide infra).
  • 67
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    • Ph.D. Dissertation, University of Arkansas, Fayetteville, AR
    • Brubaker, D. M. Ph.D. Dissertation, University of Arkansas, Fayetteville, AR, 1978.
    • (1978)
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    • note
    • α portion of all these transition states, are identical.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.