Witanowski, Michal and Roberts, John D. (1966) Proton Magnetic Resonance Spectroscopy. Configurational Stability of Neohexyl(3,3-dimethylbutyl) Organometallic Compounds. Journal of the American Chemical Society, 88 (4). pp. 737-741. ISSN 0002-7863. doi:10.1021/ja00956a023. https://resolver.caltech.edu/CaltechAUTHORS:20151014-144944013
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Abstract
The proton resonance spectra of dilute ether solutions of neohexyl(3,3-dimethylbutyl) organometallic compounds have been investigated as a function of temperature as a means of determining their configurational stabilities. Neohexyllithium, dineohexylmagnesium (free from magnesium chloride), and dineohexylzinc appear to undergo the inversion of configuration at the a-methylene groups at various temperatures. The activation energies for inversion are approximately 15, 20, and 26 kcal. for the lithium, magnesium, and zinc compounds, respectively. Inversion appears to be a first-order process for the lithium and magnesium compounds. This fact and the general dependence of the inversion rate on the nature of the metal suggest a dissociation-recombination mechanism (SE1). Trineohexylaluminum and dineohexylmercury were found to be configurationally stable up to 150-160º. The chemical shifts of the CH_2-CH_2 groupings in these organometallic compounds can be correlated with the electronegativity of the metal atoms.
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| Additional Information: | © 1966 American Chemical Society. Received September 27, 1965. Supported in part by the National Science Foundation and the Office of Naval Research. | |||||||||
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| Issue or Number: | 4 | |||||||||
| DOI: | 10.1021/ja00956a023 | |||||||||
| Record Number: | CaltechAUTHORS:20151014-144944013 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151014-144944013 | |||||||||
| Official Citation: | Proton Magnetic Resonance Spectroscopy. Configurational Stability of Neohexyl(3,3-dimethylbutyl) Organometallic Compounds1 Michal Witanowski and John D. Roberts Journal of the American Chemical Society 1966 88 (4), 737-741 DOI: 10.1021/ja00956a023 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61124 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 14 Oct 2015 23:32 | |||||||||
| Last Modified: | 10 Nov 2021 22:44 |
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