How Do You Rate This Publication?       

Title:	Conformational isomerism of phenolic procyanidins: preferred conformations in organic solvents and water
Author(s):	Hatano, Tsutomu; Hemingway, Richard W.
Date:	1997
Source:	Journal Chemical Society, Perkin Trans. 2:1035-1043
Description:	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.
	View and Print this Publication (2.1 MB)
Publication Notes:	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. Our on-line publications are scanned and captured using Adobe Acrobat. During the capture process some typographical errors may occur. Please contact the SRS Webmaster, srswebmaster@fs.fed.us if you notice any errors which make this publication unuseable.
	Get the latest version of the Adobe Acrobat reader or Acrobat Reader for Windows with Search and Accessibility