Location of Repository

Variable-Temperature Study of Hydrogen-Bond Symmetry in Cyclohexene-1,2- dicarboxylate Monoanion in Chloroform-d

By Charles L Perrin and Kathryn D Burke

Abstract

The symmetry of the hydrogen bond of hydrogen cyclohexene-1,2-dicarboxylate monoanion was determined in chloroform using the NMR method of isotopic perturbation. As the temperature decreases, the 18O-induced 13C chemical-shift separations increase not only at carboxyl carbons but also at ipso (alkene) carbons. The magnitude of the ipso increase is consistent with an 18O isotope effect on carboxylic acid acidity. Therefore it is concluded that this monoanion is a mixture of tautomers in rapid equilibrium, rather than a single symmetric structure in which a chemical-shift separation arises from coupling between a desymmetrizing vibration and anharmonic isotope-dependent vibrations, which is expected to show the opposite temperature dependence

Topics: Physical Sciences and Mathematics
Publisher: eScholarship, University of California
Year: 2014
OAI identifier:
Download PDF:
Sorry, we are unable to provide the full text but you may find it at the following location(s):
  • http://www.escholarship.org/uc... (external link)
  • Suggested articles


    To submit an update or takedown request for this paper, please submit an Update/Correction/Removal Request.