Theoretical Study on the Hydrogen Bonding Interactions in Complexes of 5-Hydroxytryptamine with Water

Authors

  • Lingfei Guo,

    1. Tianjin Key Laboratory of Structure and Performance for Functional Molecules; Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education; College of Chemistry, Tianjin Normal University, Tianjin 300387, China
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  • Zhengguo Huang,

    Corresponding author
    1. Tianjin Key Laboratory of Structure and Performance for Functional Molecules; Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education; College of Chemistry, Tianjin Normal University, Tianjin 300387, China
    • Tianjin Key Laboratory of Structure and Performance for Functional Molecules; Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education; College of Chemistry, Tianjin Normal University, Tianjin 300387, China
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  • Tingting Shen,

    1. Tianjin Key Laboratory of Structure and Performance for Functional Molecules; Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education; College of Chemistry, Tianjin Normal University, Tianjin 300387, China
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  • Lingling Ma,

    1. Tianjin Key Laboratory of Structure and Performance for Functional Molecules; Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education; College of Chemistry, Tianjin Normal University, Tianjin 300387, China
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  • Xiqian Niu

    1. Tianjin Key Laboratory of Structure and Performance for Functional Molecules; Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education; College of Chemistry, Tianjin Normal University, Tianjin 300387, China
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Abstract

The energies, geometries and harmonic vibrational frequencies of 1:1 5-hydroxytryptamine-water (5-HT-H2O) complexes are studied at the MP2/6-311++G(d,p) level. Natural bond orbital (NBO), quantum theory of atoms in molecules (QTAIM) analyses and the localized molecular orbital energy decomposition analysis (LMO-EDA) were performed to explore the nature of the hydrogen-bonding interactions in these complexes. Various types of hydrogen bonds (H-bonds) are formed in these 5-HT-H2O complexes. The intermolecular C4H55-HT···Ow H-bond in HTW3 is strengthened due to the cooperativity, whereas no such cooperativity is found in the other 5-HT-H2O complexes. H-bond in which nitrogen atom of amino in 5-HT acted as proton donors was stronger than other H-bonds. Our researches show that the hydrogen bonding interaction plays a vital role on the relative stabilities of 5-HT-H2O complexes.

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