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Empirical surface polarity parameters for native polysaccharides
Author(s) -
Fischer K.,
Spange S.
Publication year - 2000
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/1521-3935(20001001)201:15<1922::aid-macp1922>3.0.co;2-y
Subject(s) - solvatochromism , polarizability , chemistry , cellobiose , polarity (international relations) , cellulose , solvation , benzophenone , polysaccharide , solvent , computational chemistry , crystallography , stereochemistry , polymer chemistry , organic chemistry , molecule , biochemistry , cell , cellulase
The empirical Kamlet‐Taft solvatochromic polarity parameters α, β, and π* as well as calculated Reichardt's E T (30) values are presented for microcristalline cellulose, cellobiose, chitine, amylose, amylopectine, and glycogene. For this purpose, the following solvatochromic polarity indicators were applied: 2,6‐diphenyl‐4‐(2,4,6‐triphenyl‐1‐pyridinio)phenolate ( 1 ), [4,4′‐bis( N , N ‐dimethylamino)benzophenone] ( 2 ), dicyano‐bis(1,10‐phenanthroline) iron(II) [Fe(phen) 2 ](CN) 2 ( 3 ), and 4‐aminobenzophenone ( 4 ). The polarity of the microcristalline environment of cellulose can be exactly parameterized in terms of the Kamlet‐Taft α, β, and π* values. The analogy of these values to those of the model compound cellobiose and of other independent literature data, i.e. calculated π* values via LSE ( L inear S olvation E nergy) relationships derived from FTIR and fluorescence measurements, is excellent. Microcristalline cellulose exhibit strong HBD properties and a rather low value of the dipolarity/polarizability. The substitution of the hydroxy group in the 2 position of the anhydroglucose unit of cellulose with the polarizable acetamido group (cellulose → chitine) significantly enhances the dipolarity/polarizability of the polysaccharide whereas the HBD capacity accordingly decreases. A generalized empirical polarity scale for native polysaccharides is suggested.