Carbanion Stabilization by Adjacent Sulfur: Polarizability, Resonance, or Negative Hyperconjugation? Experimental Distinction Based on Intrinsic Rate Constants of Proton Transfer from (Phenylthio)nitromethane and 1-Nitro-2-phenylethane

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1944-1953

  Bernasconi, Claude F ^a   Kittredge, Kevin W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000527297     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9719463     Document Type: Article

References (59)

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48. 22 It is the fact that the experimental rate constant is not enhanced as much as one would expect if the resonance effect were developed in proportion to the degree of proton transfers which leads to the reduction in the intrinsic rate constant. We add this clarification in response to a referee's comment.
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