Chlorine Isotope Effects in the Reactions of Benzyl and Substituted Benzyl Chlorides with Various Nucleophiles

1962 ◽  
Vol 84 (14) ◽  
pp. 2763-2769 ◽  
Author(s):  
John W. Hill ◽  
Arthur. Fry
2007 ◽  
Vol 41 (13) ◽  
pp. 4662-4668 ◽  
Author(s):  
Thomas B. Hofstetter ◽  
Christopher M. Reddy ◽  
Linnea J. Heraty ◽  
Michael Berg ◽  
Neil C. Sturchio

2019 ◽  
Vol 53 (8) ◽  
pp. 4245-4254 ◽  
Author(s):  
Christina Lihl ◽  
Lisa M. Douglas ◽  
Steffi Franke ◽  
Alfredo Pérez-de-Mora ◽  
Armin H. Meyer ◽  
...  

1986 ◽  
Vol 64 (6) ◽  
pp. 1201-1205 ◽  
Author(s):  
Duncan J. McLennan ◽  
Allan R. Stein ◽  
Brian Dobson

Kinetic chlorine isotope effects attending the solvolysis of several ring-substituted 1-phenylethyl chlorides in alcohol–water solvent mixtures are reported. The k35/k37 values are insensitive to the identity of ring substituents and to solvent composition. Results are interpreted in terms of an SN1 heterolytic process incorporating a significant amount of internal return. Theoretical calculations suggest that the incipient chloride ion in the transition state may be strongly hydrogen-bonded.


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