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Preparation, Characterisation, and Structure of N ‐Methylated Derivatives of 1,3,5‐Triamino‐1,3,5‐trideoxy‐ cis ‐inositol: Polyalcohols with Unusual Acidity
Author(s) -
Hegetschweiler Kaspar,
Erni Isidor,
Schneider Walter,
Schmalle Helmut
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730110
Subject(s) - chemistry , inositol , intramolecular force , intermolecular force , solubility , cyclohexane , stereochemistry , tris , solvent , residue (chemistry) , tetramethylammonium , medicinal chemistry , organic chemistry , ion , molecule , biochemistry , receptor
1,3,5‐Trideoxy‐1,3,5‐tris(dimethylamino)‐ cis ‐inositol (TDCI) and 1,3,5‐trideoxy‐1,3,5‐tris(trimethylammonio)‐ cis ‐inositol (TTCI) were prepared by methylation of 1,3,5‐triamino‐1,3,5‐trideoxy‐ cis ‐inositol (TACI). The ability of TDCI to form both intermolecular and intramolecular H‐bonds, as demonstrated by X‐ray diffraction, is probably responsible for the good solubility of TDCI in almost every common solvent. TTCI was found to be a polyol of unusual high acidity (p K 1 = 8.14 ± 0.02, p K 2 = 13.0 ± 0.2). This phenomenon could be explained by electrostatic interactions between the charged substituents of the cyclohexane residue.