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Theoretical investigation into the cooperativity effect of 1,4-dimethoxy-d-glucosamine complex with Na+ and H2O

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Abstract

In order to explore the essence of the hydration process of chitin or chitosan in the presence of cation, the cooperativity effects between the H-bonding and Na+···molecule interactions in the 1,4-dimethoxy-d-glucosamine (DMGA) complexes with H2O and Na+ were investigated at the B3LYP/6-311++G(d,p), M06-2X/6-311++G(2df,2p), and ωB97X-D/6-311++G(2df,2p) levels. The result shows that the complexes in which Na+ or H2O is bonded simultaneously to the –NH and –OH groups connected to the C3 atom of DMGA are the most stable. The cooperativity and anti-cooperativity effects occur in DMGA···H2O···DMGA and DMGA···Na+···H2O, while only the cooperativities are confirmed in DMGA···Na+···DMGA. The cooperativity occurs in the DMGA···Na+···H2O complexes without the hydration, while the anti-cooperativity occurs in those with the hydration. Furthermore, the cooperativity and anti-cooperativity in DMGA···Na+···H2O are far stronger than those in DMGA···Na+···DMGA or DMGA···H2O···DMGA. Therefore, a deduction is given that the cooperativity and anti-cooperativity effects play an important role in the hydration of chitin or chitosan in the presence of Na+. When only Na+ is linked with –OH and –NH groups of chitosan or chitin, due to the cooperativity effect, the hydration does not occur. When both Na+ and H2O are linked with –OH and –NH groups, the anti-cooperativities are dominant in controlling of the aggregation process of Na+, H2O, chitosan, and chitin, leading to the possible hydration. Atoms in molecules (AIM) analysis confirms the cooperativity and anti-cooperativity effects.

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  1. Department of Environment and Security Engineering, Taiyuan institute of technology, Taiyuan, 030008, People’s Republic of China

    Jin-an Zhao

  2. School of Chemical Engineering and Technology, North University of China, Taiyuan, 030051, People’s Republic of China

    Fu-de Ren

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Correspondence to Jin-an Zhao.

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ESM 1

Interaction energies of the binary systems DMGA···H2O, DMGA···Na+, Na+···H2O and DMGA···DMGA at three levels of theory, the optimized geometries of the binary systems DMGA···DMGA, DMGA···H2O, DMGA···Na+ and ternary systems DMGA···H2O···DMGA, DMGA···Na+···DMGA, DMGA···Na+···H2O as well as their AIM results at the B3LYP/6-311++G(d,p) level are collected in Supplementary data. (DOC 6110 kb)

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Zhao, Ja., Ren, Fd. Theoretical investigation into the cooperativity effect of 1,4-dimethoxy-d-glucosamine complex with Na+ and H2O. J Mol Model 26, 203 (2020). https://doi.org/10.1007/s00894-020-04461-x

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