CaltechAUTHORS
Published August 22, 2002 | public
Journal Article Metadata-only

The Conformations of 1,4-Butanedioic Acid as a Function of Solvent Polarity in a Series of Alcohols as Determined by NMR Spectroscopy

Williams, Leslie Nicole
Petterson, Krag A.
Roberts, John D.
An error occurred while generating the citation.

Abstract

Vicinal proton−proton NMR couplings have been employed to estimate the differences in conformational equilibria for 1,4-butanedioic-2,3-^(13)C_2 acid in the progression of its diprotic to monoprotic to di-ionized forms as a function of solvent in water and in a series of alcohols ranging from methanol to tert-butyl alcohol. Except for water, the percentage of gauche increases from diacid to monoanion and then decreases from monoanion to dianion. The substantial gauche preference for the monoanion species in the less-polar alcohols is clearly the result of intramolecular hydrogen bonding.

Additional Information

© 2002 American Chemical Society. Received: August 18, 2001; In Final Form: December 31, 2001. Publication Date (Web): February 20, 2002. Acknowledgment is made to the donors of the Petroleum Research Fund administered by the American Chemical Society, for support of this research. We are also deeply indebted to the Summer Undergraduate Research Fellowship Program (SURF), the Howard Hughes Medical Institute, the E. I. Du Pont Company, Dr. & Mrs. Chester M. McCloskey, and the Camille and Henry Dreyfus Foundation for their helpful financial assistance. We greatly appreciate the assistance of Jennifer Milicent Lindsay in preliminary experiments. This paper is dedicated to the memory of the late G. Wilse Robinson, a warm friend, a very stimulating colleague, and an extraordinarily original and perceptive scientist.

Additional details

Identifiers Funding Dates
Created:
August 19, 2023
Modified:
October 24, 2023