Cryptands as bases in proton-transfer reactions. The rates and hydrogen isotope effects in the ionization of ethyl nitroacetate by cryptands

1979 ◽  
pp. 1293 ◽  
Author(s):  
Brian G. Cox ◽  
Hermann Schneider
Keyword(s):  
Proton Transfer ◽  
Hydrogen Isotope ◽  
Isotope Effects ◽  
Transfer Reactions ◽  
Proton Transfer Reactions ◽  
Ethyl Nitroacetate

Kinetic hydrogen isotope effects in the ionization of some nitroparaffins

1966 ◽  
Vol 294 (1438) ◽  
pp. 273-297 ◽  
Keyword(s):  
Proton Transfer ◽  
Isotope Effect ◽  
Hydrogen Isotope ◽  
Isotope Effects ◽  
Transfer Reactions ◽  
Acid Base ◽  
Maximum Value ◽  
Proton Transfers ◽  
Theoretical Predictions ◽  
Proton Transfer Reactions

Values are reported for the kinetic hydrogen isotope effects for proton-transfer reactions between hydroxide ions and nitromethane, nitroethane, nitrocyclohexane and 2-nitropropane, and between 2-nitropropane and pyridine, 2, 6-lutidine and acetate ions. In conjunction with earlier work the results suggest that the isotope effect has a maximum value for proton transfers between two acid-base systems of approximately equal p K , in agreement with theoretical predictions. We have confirmed that the abstraction of a proton from 2-nitropropane by 2, 6-lutidine exhibits an abnormally high isotope effect ( k H / k D = 20), probably attributable to a considerable tunnelling correction.

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