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ARS Home » Southeast Area » New Orleans, Louisiana » Southern Regional Research Center » Cotton Structure and Quality Research » Research » Publications at this Location » Publication #310584
Title: Quantum mechanics models of the methanol dimer: O-H…O hydrogen bonds of ß-D-glucose moieties from crystallographic data

Author
item Santiago Cintron, Michael
item Johnson, Glenn
item FRENCH, ALFRED - Retired ARS Employee

Submitted to: Carbohydrate Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/7/2017
Publication Date: 3/19/2017
Citation: Santiago Cintron, M., Johnson, G.P., French, A. 2017. Quantum mechanics models of the methanol dimer: O-H…O hydrogen bonds of ß-D-glucose moieties from crystallographic data. Carbohydrate Research. 443-444:87-94. https://doi.org/10.1016/j.carres.2017.03.007.
DOI: https://doi.org/10.1016/j.carres.2017.03.007

Interpretive Summary: In this study, a database of crystallographic data was surveyed for all donor-acceptor interactions in ß-D-glucose structures. This search was performed in order to examine the similarities and differences among the different alcohol groups and other oxygen atoms that participate in the hydrogen bonds. Comparable behavior was observed for the alcohol groups at the O2, O3, O4, and O6 atoms. The interaction of two carbohydrates using methanol dimer models was modeled using quantum mechanics (QM) calculations. Surface energy plots for hydrogen bonding distance (H…O) and angle (O-H…O) were constructed based on QM calculations that used two levels of theory for the calculations, B3LYP 6-31+G* for full minimizations, and B3LYP 6-311+G** for single-point energy determinations. At each of the 399 geometries examined, the structures were also analyzed in terms of Bader’s atoms-in-molecules theory. This analysis showed a widespread ability by the dimer models to form electron sharing O-H…O hydrogen bonds.

Technical Abstract: In this study, a survey of the Cambridge Crystal Structure Database for all donor-acceptor interactions in ß-D-glucose moieties was performed to examine the similarities and differences among the different hydroxyl groups and ether oxygen atoms that participate in hydrogen bonds. Comparable behavior was observed for the O2-H, O3-H, O4-H, and O6-H hydroxyls. The interaction of two carbohydrates using methanol dimer models was modeled using quantum mechanics (QM). Surface energy plots for hydrogen bonding distance (H…O) and angle (O-H…O) were constructed based on QM calculations that used B3LYP 6-31+G* for full minimizations, and B3LYP 6-311+G** for single-point energy determinations. At each of the 399 geometries, the structures were analyzed in terms of Bader’s atoms-in-molecules theory. This analysis showed a widespread ability by the dimer models to form electron sharing O-H…O hydrogen bonds.