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Published December 4, 2008 | public
Journal Article

Determination of the Dihedral Angle of the Monoanion of Succinic Acid in Aprotic Media

Abstract

A value of 74(±4)° was determined from NMR-observed dipolar couplings for the rotational dihedral angle of the monosuccinate anion in an aprotic liquid-crystal solution of the gauche conformation of tetraoctylammonium monosuccinate. This value is in reasonable agreement with other, somewhat less definitive, evidence gleaned from isotropic vicinal proton−proton couplings of the essentially completely gauche preference of the monosuccinate anion in tert-butyl alcohol and aprotic solvents, such as DMSO and THF, and quantum computations for the monoanion in THF.

Additional Information

Copyright © 2008 American Chemical Society. Received: February 14, 2008; Revised Manuscript Received: September 16, 2008. Publication Date (Web): October 30, 2008. This research was supported by the National Science Foundation under Grant No. CHE-0543620. Acknowledgement is also made to the Summer Undergraduate Research Fellowship Program (SURF) at the California Institute of Technology, which provided a Howard Hughes Medical Institute Fellowship to A.A.S., and the Senior Scientist Mentor Program of the Camille and Henry Dreyfus Foundation. In addition, we are indebted to Merck & Company, Dr. and Mrs. Chester M. McCloskey, Dr. David J. Mathre, and Edith M. Roberts for their helpful financial assistance for funding of this area of our research.

Additional details

Created:
August 20, 2023
Modified:
October 17, 2023