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The question of intramolecular hydrogen bonding in 2-flouroethanol

Griffith, Ronald G. and Roberts, John D. (1974) The question of intramolecular hydrogen bonding in 2-flouroethanol. Tetrahedron Letters, 15 (39). pp. 3499-3502. ISSN 0040-4039. doi:10.1016/S0040-4039(01)91947-1.

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Several investigations have shown, by a variety of spectral techniques, that 2-fluoroethanol (1) exists both in the liquid and vapor state, predominantly (>95%) in the conformation. with hydroxyl and fluorine gauche to one another. Notable is the recent electron-diffraction study in which 1 was shown to be greater than 90% gauche in the vapor phase at 156°. In every instance, this marked conformational preference for the gauche form has been attributed to the formation of a strong intramolecular hydrogen bond between the electronegative fluorine atom and the hydroxyl proton which are in close proximity in this configuration. That this is the case is presumably also supported by the observation that the CCF bond angle of 107.7° is compressed relative to fluoroethane.

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Additional Information:© 1974 Pergamon Press. Received in USA 24 May 1974; received in UK for publication 16 August 1974. Supported by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry4893
Issue or Number:39
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Official Citation:Ronald G. Griffith, John D. Roberts, The question of intramolecular hydrogen bonding in 2-flouroethanol, Tetrahedron Letters, Volume 15, Issue 39, 1974, Pages 3499-3502, ISSN 0040-4039, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61495
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 22:25
Last Modified:10 Nov 2021 22:49

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