Published July 1, 1981
| Version v1
Journal article
General acid catalysis of alcohol heterolysis
Description
The conversion of diferrocenylphenylmethanol (5) into the carbocation is general acid catalyzed in H2O:CH3CN, 1:1 w/w, and α = 0.88. The corresponding reaction of tropyl alcohol is also general acid catalyzed, and α = 0.71 and 0.90 in water and H2O:CH3CN, 1:1 w/w, respectively. However, the hydrogen ion catalyzed reactions have inverse solvent kinetic hydrogen isotope effects, and k/sub H20//k/sub D20/ = 0.56 for reaction of 5 in H2O(D2O):CH3CN. Consideration of the equilibrium constants for alcohol protonation suggests that acid-catalyzed conversion of alcohol into carbocation should go from stepwise to concerted as the stability of the carbocation is increased
Additional details
Publishing Information
- Journal Title
- J. Am. Chem. Soc.
- Journal Volume
- 103
- Journal Issue
- 13
- Series
- J. Am. Chem. Soc.
- Journal Page Range
- 3855-3858
- ISSN
- 0002-7863
INIS
- Country of Publication
- United States
- Country of Input or Organization
- United States
- INIS RN
- 12631841
- Subject category
- S37: INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY;
- Resource subtype / Literary indicator
- Numerical Data
- Descriptors DEI
- ACETONITRILE; ALCOHOLS; CATALYSIS; DECOMPOSITION; DEUTERIUM; EXPERIMENTAL DATA; HYDROCHLORIC ACID; IRON COMPLEXES; ISOTOPE EFFECTS; ORGANIC ACIDS; WATER
- Descriptors DEC
- CHEMICAL REACTIONS; CHLORINE COMPOUNDS; COMPLEXES; DATA; HALOGEN COMPOUNDS; HYDROGEN COMPOUNDS; HYDROGEN ISOTOPES; HYDROXY COMPOUNDS; INFORMATION; INORGANIC ACIDS; ISOTOPES; LIGHT NUCLEI; NITRILES; NUCLEI; NUMERICAL DATA; ODD-ODD NUCLEI; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; OXYGEN COMPOUNDS; STABLE ISOTOPES; TRANSITION ELEMENT COMPLEXES