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Microsolvation effect and hydrogen-bonding pattern of taurine-water TA-(H2O)n (n = 1–3) complexes

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Abstract

The microsolvation of taurine (TA) with one, two or three water molecules was investigated by a density functional theory (DFT) approach. Quantum theory of atoms in molecules (QTAIM) analyses were employed to elucidate the hydrogen bond (H-bond) interaction characteristics in TA-(H2O)n (n = 1–3) complexes. The results showed that the intramolecular H-bond formed between the hydroxyl and the N atom of TA are retained in most TA-(H2O)n (n = 1–3) complexes, and are strengthened via cooperative effects among multiple H-bonds from n = 1–3. A trend of proton transformation exists from the hydroxyl to the N atom, which finally results in the cleavage of the origin intramolecular H-bond and the formation of a new intramolecular H-bond between the amino and the O atom of TA. Therefore, the most stable TA-(H2O)3 complex becomes a zwitterionic complex rather than a neutral type. A many-body interaction analysis showed that the major contributors to the binding energies for complexes are the two-body energies, while three-body energies and relaxation energies make significant contributions to the binding energies for some complexes, whereas the four-body energies are too small to be significant.

The microsolvation of taurine (TA) with 1–3 water molecules was investigated by a density functional theory (DFT) approach. Quantum theory of atoms in molecules (QTAIM) and many-body interaction analyses were employed to elucidate hydrogen bonding interaction characteristics in TA-(H2O)n (n = 1–3) complexes

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Acknowledgments

This work is supported by Tianjin Science and Technology Development Fund Projects in Colleges and Universities (No. 20080504).

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Authors and Affiliations

  1. Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin, 300387, People’s Republic of China

    Yumei Dai, Zhengguo Huang, Hongke Wang & Lei Yu

  2. College of Materials Science and Engineering, Shijiazhuang Tiedao University, Shijiazhuang, Hebei, 050043, People’s Republic of China

    Yuhua Wang

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  1. Yumei Dai
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Correspondence to Zhengguo Huang.

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Dai, Y., Wang, Y., Huang, Z. et al. Microsolvation effect and hydrogen-bonding pattern of taurine-water TA-(H2O)n (n = 1–3) complexes. J Mol Model 18, 265–274 (2012). https://doi.org/10.1007/s00894-011-1070-z

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