Skip to Main Content
U.S. Forest Service
Caring for the land and serving people

United States Department of Agriculture

Home > Search > Publication Information

  1. Share via EmailShare on FacebookShare on LinkedInShare on Twitter
    Dislike this pubLike this pub
    Author(s): Tsutomu Hatano; Richard W. Hemingway
    Date: 1997
    Source: Journal Chemical Society, Perkin Trans. 2:1035-1043
    Publication Series: Miscellaneous Publication
    PDF: Download Publication  (2.1 MB)


    NMR studies of catechin-{4α→8)-epicatechin (I) and catechin-{4α→8)-catechin (2) provided complete assignment of the proton and carbon resonances for both the more extended and compact conformers in the free phenolic form. When 1 is in organic solvents, the more extended rotamer is preferred over the more compact rotamer (10:7), but in water, the compact rotamer dominates (2:10). When 2 is in organic solvents, the more compact rotamer is slightly preferred (8:10), but in water, only trace amounts of the more extended rotamer are detected. NOE experiments show rotational conformation exchange despite the fact that two distinct and sharp sets of signals are seen for each rotamer. The upper unit heterocyclic ring exists in an approximate half-chair conformation in each rotamer for both dimers. However, coupling constants of the lower unit heterocycles show substantial axial orientation of the B-ring. Lineshape analysis of the terminal unit H-3F excludes E- and A-conformational interchange. These results and NOE experiments show a skewed-boat conformation for the terminal unit in 1 and between a half-chair and skewed-boat conformation for the terminal unit in 2.

    Publication Notes

    • You may send email to to request a hard copy of this publication.
    • (Please specify exactly which publication you are requesting and your mailing address.)
    • We recommend that you also print this page and attach it to the printout of the article, to retain the full citation information.
    • This article was written and prepared by U.S. Government employees on official time, and is therefore in the public domain.


    Hatano, Tsutomu; Hemingway, Richard W. 1997. Conformational isomerism of phenolic procyanidins: preferred conformations in organic solvents and water. Journal Chemical Society, Perkin Trans. 2:1035-1043

    Related Search

    XML: View XML
Show More
Show Fewer
Jump to Top of Page