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Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G* and 6–311 +  + G(d,p) basis sets

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Abstract

Rare sugars are monosaccharides with tremendous potential for applications in pharmaceutical, cosmetics, nutraceutical, and flavors industries. The four rare sugars, including gulose, allose, altrose, and talose, are stereoisomers that are different in the hydroxyl group orientation (axial or equatorial) on the C2-4 atoms. The basis sets effect in evaluation of the possibility intramolecular hydrogen bonding (H-bonds) in the selected rare sugars was studied from 6-31G* to 6–311 ++ G(d,p) basis sets using DFT, AIM, and NBO methods. The results show that the selected rare sugars are more stable at 6–311 ++ G(d,p) basis sets compared to 6-31G* because their electronic energies were reduced between 158 and 164 (kcal.mol−1). The overall effect of basis set enhancement is to decrease H-bond energies in the range of  1.25 to 2.51 (kcal.mol−1) and stabilization energies between 2 and 5 (kcal.mol−1) in the selected rare sugars at the DFT level of theory. The intramolecular H-bond distances, H-bond energies obtained from the AIM analysis, and also the second-order stabilization energies obtained from the NBO analysis were fluctuated largely depending on the basis set. In summary, it was found that the use of 6–311 ++ G(d,p) basis set to be more efficient results in rare sugars geometry than the 6-31G* basis set.

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Data availability

The datasets generated and/or analyzed during the current study are available from the corresponding author on reasonable request.

Code availability

Spartan 14 –Gaussian 09.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Zahrabatoul Mosapour Kotena

  2. Department of Chemistry, Sharif University & Technology, P.O. Box 11365-9516, Tehran, Iran

    Zahrabatoul Mosapour Kotena

  3. Department of Agricultural Science & Food Industries, Science & Research Branch, Islamic Azad University, Tehran, Iran

    Mozhan Razi

  4. Department of Chemistry, Firoozabad Branch, Islamic Azad University, Firoozabad, Iran

    Sara Ahmadi

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  1. Zahrabatoul Mosapour Kotena
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  2. Mozhan Razi
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  3. Sara Ahmadi
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection, and analysis were performed by Zahrabatoul Mosapour Kotena, Mozhan Razi, and Sara Ahmadi. The first draft of the manuscript was written by Zahrabatoul Mosapour Kotena, and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Zahrabatoul Mosapour Kotena.

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Mosapour Kotena, Z., Razi, M. & Ahmadi, S. Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G* and 6–311 +  + G(d,p) basis sets. J Mol Model 27, 315 (2021). https://doi.org/10.1007/s00894-021-04916-9

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