Model calculations of kinetic isotope effects in the SN2 reaction of benzyl arenesulfonates with N,N-dimethyl-p-toluidine

1981 ◽  
Vol 85 (15) ◽  
pp. 2281-2286 ◽  
Author(s):  
Hiroshi Yamataka ◽  
Takashi Ando
Keyword(s):  
Isotope Effects ◽  
Kinetic Isotope Effects ◽  
Model Calculations ◽  
Kinetic Isotope ◽  
Sn2 Reaction

The Effect of Solvent on the Structure of the Transition State for the SN2 Reaction between Cyanide Ion and Ethyl Chloride in DMSO and THF Probed with Six Different Kinetic Isotope Effects

2006 ◽  
Vol 71 (13) ◽  
pp. 4742-4747 ◽  
Author(s):  
Yao-ren Fang ◽  
Susanna MacMillar ◽  
Jonas Eriksson ◽  
Magdalena Kołodziejska-Huben ◽  
Agnieszka Dybała-Defratyka ◽  
...  
Keyword(s):  
Transition State ◽  
Isotope Effects ◽  
Kinetic Isotope Effects ◽  
Ethyl Chloride ◽  
Cyanide Ion ◽  
Effect Of Solvent ◽  
Kinetic Isotope ◽  
Sn2 Reaction

Model Calculations of Kinetic Isotope Effects in Nucleophilic Substitution Reactions

1974 ◽  
Vol 52 (6) ◽  
pp. 903-909 ◽  
Author(s):  
Jan Bron
Keyword(s):  
Transition State ◽  
Isotope Effects ◽  
Benzyl Bromide ◽  
Kinetic Isotope Effects ◽  
Substitution Reactions ◽  
Model Calculations ◽  
Kinetic Isotope ◽  
Proposed Model ◽  
Standard Reaction ◽  
Deuterium Isotope Effects

The results of calculations indicate that a previously proposed model for the transition state in "borderline" substitution reactions can be generalized and, as a result, the observed differences in the carbon-13 and deuterium isotope effects of SN1, SN2, and "borderline" reactions rationalized. Although the conclusions may apply more generally, the standard reaction investigated is the solvolysis of benzyl bromide. The importance of resonance interaction with the phenyl ring, the significance of the product- or reactant-like character of the transition state, and the influence of the magnitude of force constants in determining isotope effects are examined. The temperature dependence of kinetic isotope effects in solvolysis is also investigated.

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