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Proton Magnetic Resonance Spectroscopy. Configurational Stability of Neohexyl(3,3-dimethylbutyl) Organometallic Compounds

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. http://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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http://dx.doi.org/10.1021/ja00956a023DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00956a023PublisherArticle
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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Office of Naval Research (ONR)UNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3251
Record Number:CaltechAUTHORS:20151014-144944013
Persistent URL:http://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:14 Oct 2015 23:32

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