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Published March 1, 1970 | public
Journal Article

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

Abstract

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.

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.

Additional details

Created:
August 19, 2023
Modified:
October 24, 2023