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Structures, stability and hydrogen bonding in inositol conformers.

Nazia Siddiqui1, Vijay Singh, Milind M Deshmukh

  • 1Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016 India. gurunath@iitk.ac.in.

Physical Chemistry Chemical Physics : PCCP
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The stability of inositol stereoisomers depends on solvent polarity. Scyllo-inositol is most stable in polar solvents due to weaker intramolecular hydrogen bonds, as shown by ab initio calculations.

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Area of Science:

  • Computational Chemistry
  • Molecular Modeling
  • Biochemistry

Background:

  • Inositol stereoisomers exhibit diverse properties influencing their biological roles.
  • Understanding the energetic landscape of inositol isomers is crucial for predicting their behavior in different environments.
  • Intramolecular hydrogen bonding significantly impacts molecular stability and conformation.

Purpose of the Study:

  • To investigate the relative stability of thirteen theoretically possible inositol stereoisomers.
  • To elucidate the influence of solvent polarity on inositol isomer stability.
  • To quantify the strength of intramolecular hydrogen bonds in different inositol isomers.

Main Methods:

  • Employed ab initio computational methods including density-functional theory (DFT), second-order Möller-Plesset perturbation (MP2), and self-consistent reaction field (SCRF) theories.
  • Performed gas phase and polar solvent calculations to assess energetic differences.
  • Utilized the molecular tailoring approach (MTA) to estimate individual hydrogen bond energies.

Main Results:

  • In gas phase, myo- and neo-inositol isomers are marginally more stable than scyllo-inositol.
  • In polar solvents, scyllo-inositol emerges as the most stable isomer.
  • Hydrogen bond energy analysis revealed a hierarchy of strength: axial-axial > equatorial-axial > axial-equatorial > equatorial-equatorial, with scyllo-inositol exhibiting the weakest intramolecular hydrogen bonds.

Conclusions:

  • Solvent polarity plays a critical role in determining the preferred inositol stereoisomer.
  • Weaker intramolecular hydrogen bonds in scyllo-inositol account for its enhanced stability in polar environments.
  • Computational methods accurately predict hydrogen bond strengths, correlating well with experimental data.