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Issue 28, 2015
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Structures, stability and hydrogen bonding in inositol conformers

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Abstract

Various ab initio calculations using the density-functional (DFT), the second order Möller–Plesset perturbation (MP2) and self-consistent reaction field (SCRF) theories were performed on thirteen theoretically possible inositol stereoisomers. Gas phase calculations reveal that the myo- and neo-isomers of inositol (bearing one and two axial hydroxyl groups, respectively) are marginally more stable (by 0.5 kcal mol−1) than the all equatorially substituted scyllo-inositol. The calculations when done in different polar solvents show that the scyllo-inositol becomes the most stable inositol isomer, a fact attributed to weaker intramolecular hydrogen bonds. The individual hydrogen bond energy in all the isomers of inositol was also estimated using the molecular tailoring approach (MTA). The calculated hydrogen bond energies in these isomers are in excellent agreement with reported O–H⋯O hydrogen bond distances and νO–H stretching frequencies. The estimated H-bond energy values suggest that the order of the intramolecular hydrogen bond strength follows: axial–axial > equatorial–axial > axial–equatorial > equatorial–equatorial hydrogen bonds. The intramolecular hydrogen bonds in the scyllo isomer are much weaker than those in other conformers, thus making this isomer more stable in polar solvents.

Graphical abstract: Structures, stability and hydrogen bonding in inositol conformers

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Article information


Submitted
09 May 2015
Accepted
05 Jun 2015
First published
10 Jun 2015

This article is Open Access

Phys. Chem. Chem. Phys., 2015,17, 18514-18523
Article type
Paper
Author version available

Structures, stability and hydrogen bonding in inositol conformers

N. Siddiqui, V. Singh, M. M. Deshmukh and R. Gurunath, Phys. Chem. Chem. Phys., 2015, 17, 18514
DOI: 10.1039/C5CP02690C

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