CaltechAUTHORS
  A Caltech Library Service

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 and Petterson, Krag A. and Roberts, John D. (2002) The Conformations of 1,4-Butanedioic Acid as a Function of Solvent Polarity in a Series of Alcohols as Determined by NMR Spectroscopy. Journal of Physical Chemistry A, 106 (33). pp. 7491-7493. ISSN 1089-5639. http://resolver.caltech.edu/CaltechAUTHORS:20151001-101403834

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: http://resolver.caltech.edu/CaltechAUTHORS:20151001-101403834

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jp013220nDOIArticle
http://pubs.acs.org/doi/abs/10.1021/jp013220nPublisherArticle
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.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
E. I. Du Pont CompanyUNSPECIFIED
Dr. and Mrs. Chester M. McCloskeyUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Record Number:CaltechAUTHORS:20151001-101403834
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151001-101403834
Official Citation:The Conformations of 1,4-Butanedioic Acid as a Function of Solvent Polarity in a Series of Alcohols as Determined by NMR Spectroscopy Leslie Nicole Williams, Krag A. Petterson, and John D. Roberts The Journal of Physical Chemistry A 2002 106 (33), 7491-7493 DOI: 10.1021/jp013220n
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60656
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:01 Oct 2015 22:44
Last Modified:01 Oct 2015 22:44

Repository Staff Only: item control page