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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

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 equato...

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Main Authors: Kotena, Zahrabatoul Mosapour, Razi, Mozhan, Ahmadi, Sara
Format: Article
Published: Springer 2021
Subjects:
QC Physics
QD Chemistry
T Technology (General)
Online Access:http://eprints.um.edu.my/26999/
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spelling my.um.eprints.269992022-04-14T02:51:55Z http://eprints.um.edu.my/26999/ Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets Kotena, Zahrabatoul Mosapour Razi, Mozhan Ahmadi, Sara QC Physics QD Chemistry T Technology (General) 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. Springer 2021-11 Article PeerReviewed Kotena, Zahrabatoul Mosapour and Razi, Mozhan and Ahmadi, Sara (2021) Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets. Journal of Molecular Modeling, 27 (11). ISSN 1610-2940, DOI https://doi.org/10.1007/s00894-021-04916-9 <https://doi.org/10.1007/s00894-021-04916-9>. 10.1007/s00894-021-04916-9
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QC Physics
QD Chemistry
T Technology (General)
spellingShingle QC Physics
QD Chemistry
T Technology (General)
Kotena, Zahrabatoul Mosapour
Razi, Mozhan
Ahmadi, Sara
Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets
description 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.
format Article
author Kotena, Zahrabatoul Mosapour
Razi, Mozhan
Ahmadi, Sara
author_facet Kotena, Zahrabatoul Mosapour
Razi, Mozhan
Ahmadi, Sara
author_sort Kotena, Zahrabatoul Mosapour
title Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets
title_short Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets
title_full Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets
title_fullStr Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets
title_full_unstemmed Evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31G*and 6-311++ G(d,p) basis sets
title_sort evaluation of hydrogen bonds formation in the selected rare sugars based on 6-31g*and 6-311++ g(d,p) basis sets
publisher Springer
publishDate 2021
url http://eprints.um.edu.my/26999/
_version_ 1735409486239105024
score 13.211869

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