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Pairwise interaction enthalpies of enantiomers of β‐amino alcohols in DMSO + H 2 O mixtures at 298.15 K
Author(s) -
Liang Hongyu,
Hu Xingen,
Fang Guoyong,
Shao Shuang,
Guo Aidi,
Guo Zheng
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22021
Subject(s) - chemistry , enantiomer , solvent , amino acid , titration , butanol , hydrophobic effect , alcohol , medicinal chemistry , stereochemistry , organic chemistry , ethanol , biochemistry
Abstract The dilution enthalpies of enantiomers of six β‐amino alcohols, namely ( R )‐(−)‐2‐amino‐1‐propanol versus ( S )‐(+)‐2‐amino‐1‐propanol, ( R )‐(−)‐2‐amino‐1‐butanol versus ( S )‐(+)‐2‐amino‐1‐butanol, and ( R )‐(−)‐2‐amino‐1‐pentanol versus ( S )‐(+)‐2‐amino‐1‐pentanol in dimethylsulfoxide (DMSO) + H 2 O mixtures (mass fractions of DMSO w = 0 to 0.3) have been determined respectively using an isothermal titration calorimeter (MicroCal ITC200, Northampton, MA, USA) at 298.15 K. According to the McMillan–Mayer theory, the corresponding homochiral enthalpic pairwise interaction coefficients ( h XX ) of the six amino alcohols have been calculated. It is found that across the whole studied composition range of mixed solvent, values of h XX for S‐enantiomer are almost universally higher than those of R‐enantiomer for each amino alcohol and that the variations of h XX depend largely on the composition of mixed solvent. The results were interpreted from the point of view of solute–solute interaction mediated by cosolvent DMSO, as well as competition equilibrium between hydrophobic–hydrophobic, hydrophilic–hydrophilic, and hydrophobic–hydrophilic interactions. Chirality 24:374–385, 2012 . © 2012 Wiley Periodicals, Inc.