Lifetimes of Iminium Ions in Aqueous Solution

Journal of the American Chemical Society

Volumn 117, Issue 17, 1995, Pages 4851-4857

  Eldin, Sherif ^a   Jencks, William P ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000605895     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00122a015     Document Type: Article

References (24)

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16. aPrediction for Organic Acids and Bases; Chapman and Hall: New York, 1981).
17. Considerably longer lifetimes have been reported (Koehler, K.; Sandstrom, W.; Cordes, E. H. J. Am. Chem. Soc. 1964, 86, 2413. Sollenberger, P. Y.; Martin, R. B. J. Am. Chem. Soc. 1970, 92, 4261) for iminium ions generated from aromatic enamines. The values for the lifetimes reported by Koehler et al. and Sollenberger et al. are not in conflict with the shorter lifetimes reported in this study. The iminium ions in the above reports are carbocations that are stabilized by a neighboring nitrogen atom and a phenyl ring, and therefore are expected to have relatively longer lifetimes.
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23. nucbecomes diffusion limited. In this study we are estimating the first-order rate constant for the collapse of an encounter complex, in which the diffusional step is not involved.
24. Kallen, R. G.; Jencks, W. P. J. Biol. Chem. 1966, 241, 5845.