Intermolecular chiral assemblies in R(-) and S(+) 2-butanol detected by microcalorimetry measurements

Chirality
Uri CoganMeir Shinitzky

Abstract

Supramolecular chiral assemblies of R(-) and S(+) 2-butanol, in their neat form or when dissolved in their nonchiral isomer isobutanol, were evaluated by isothermal titration calorimetry (ITC) ensuing mixing. Dilution of 0.5 M solution of R(-) 2-butanol in isobutanol into the latter liberated heat of several calories per mole, which was approximately double than that obtained in parallel dilutions of S(+) 2-butanol in isobutanol. The ITC dilution profiles indicated an estimate of about 100 isobutanol solvent molecules surrounding each of the 2-butanol enantiomers, presumably arranged in chiral configurations, with different adopted order between the isomers. Mixings of neat R and S 2-butanol were followed by endothermic ITC profiles, indicating that, in racemic 2-butanol, both the supramolecular order and the intermolecular binding energies are lower than in each of the neat chiral isomers. The diversion from symmetrical ITC patterns in these mixings indicated again a subtle difference in molecular organization between the neat enantiomers. It should be noted that the presence of impurities, α-pinene and teterhydrofuran, at a level totaling 0.5%, did not influence the ITC heat flow profiles. The findings of this study demonstra...Continue Reading

References

Aug 1, 1966·Journal of Theoretical Biology·Y Yamagata
Feb 13, 2003·Current Opinion in Structural Biology·Patricia C Weber, F Raymond Salemme
Feb 17, 2006·Physical Chemistry Chemical Physics : PCCP·Yosef ScolnikMeir Shinitzky
Aug 28, 2007·The Journal of Physical Chemistry. B·Meir ShinitzkyYitzhak Mastai
Oct 23, 2009·Astrobiology·Radu PopaRomulus Ion Scorei

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Citations

Apr 13, 2013·Chirality·Meir Shinitzky
Mar 13, 2018·Chirality·Liora Werber, Yitzhak Mastai

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