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Nuclear Magnetic Resonance Spectroscopy. Carbon-13 Chemical Shifts in Acyclic and Alicyclic Alcohols

Roberts, John D. and Weigert, Frank J. and Kroschwitz, Jacqueline I. and Reich, Hans J. (1970) Nuclear Magnetic Resonance Spectroscopy. Carbon-13 Chemical Shifts in Acyclic and Alicyclic Alcohols. Journal of the American Chemical Society, 92 (5). pp. 1338-1347. ISSN 0002-7863.

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The chemical shifts of ^(13)C in a variety of acyclic and alicyclic alcohols have been determined by high resolution nmr spectroscopy with the aid of proton decoupling. It has been found that there are rather good linear relationships between carbon chemical shifts in alcohols and analogously constituted hydrocarbons, wherein a methyl group replaces the hydroxyl group. The linear correlation coefficients for relationships of the general type δ_CROH = Aδ_CRCHa + B are better than 0.98 for shifts of corresponding ɑ (directly attached hydroxyl), β, y, and δ carbons for a variety of primary, secondary, and tertiary acyclic alcohols and cyclohexanols carrying both axial and equatorial substituents. The shifts of the carbons of a number of cycloalkanols have been investigated in hope of providing information about conformations in medium-sized ring compounds.

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Additional Information:© 1970 American Chemical Society. Received June 26, 1969. Supported by the National Science Foundation and the Public Health Service, Research Grant No. 11072-05-06 from the Division of General Medical Sciences. National Science Foundation Predoctoral Fellow, 1965-1968. National Institutes of Health Postdoctoral Fellow, 1967-1968. National Research Council of Canada Postdoctoral Fellow, 1968-1969. We are much indebted to Professor David M. Grant for providing us with information about his research on ^(13)C chemical shifts in advance of publication. The methylcyclohexanols used in this work were prepared by Mr. Vernon Cormier as part of the National Science Foundation Undergraduate Research Program. Samples of cis- and trans-1,4-di-t-butylcyclohexane were generously provided by Professor B. M. Wepster. The chemical-shift data for these substances were obtained by Dr. Manfred Jautelat.
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Public Health Service11072-05-06
NSF Predoctoral FellowshipUNSPECIFIED
NIH Postdoctoral FellowshipUNSPECIFIED
National Research Council of Canada Postdoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3887
Issue or Number:5
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Official Citation:Nuclear magnetic resonance spectroscopy. Carbon-13 chemical shifts in acyclic and alicyclic alcohols John D. Roberts, Frank J. Weigert, Jacqueline I. Kroschwitz, Hans J. Reich pp 1338–1347 Publication Date: March 1, 1970 (Article) DOI: 10.1021/ja00708a038
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61047
Deposited By: Ruth Sustaita
Deposited On:13 Oct 2015 21:13
Last Modified:03 Oct 2019 09:03

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