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Theoretical investigation on the improper hydrogen bond in κ-carrabiose⋯Y (Y = HF, HCl, HBr, NH3, H2O, and H2S) complexes

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Abstract

The nature of H-bonds in κ-carrabiose⋯Y (Y = HF, HCl, HBr, NH3, H2O, and H2S) complexes was studied. For this aim, the structure of isolated κ-carrabiose was optimized using three global hybrids functional: B3LYP, PBE0, and M06-2X combined with 6-311G** basis set. Subsequently, the κ-carrabiose in the presence of HF, HCl, HBr, NH3, H2O, and H2S was optimized using the CBS-4 M method. NBO analyses were then carried out at the MP2/6-311G** level of theory. A particular interest was focused on C(18)―H(34)⋯Y bond. The results reveal that the C(18)―H(34)⋯Y bond is an improper H-bond since a significant contraction of C(18)―H(34) was observed during the complexation leading to a significant blueshifted stretching frequency. The NBO analyses have shown that the formation of the improper H-bonds C(18)―H(34)⋯Y (Y = F, Cl, Br, N, O, and S) is principally due to the increase of the s-character of the hybrid orbital in carbon atom (rehybridization) in κ-carrabiose⋯Y complexes. Regarding the polarization, it was proved that more the H-bond center (carbon in C(18)―H(34)⋯Y) becomes less positive, the hydrogen more positive, and Y more negative; more the contraction of the C(18)―H(34) bond is important. It was also confirmed for intramolecular H-bonds in κ-carrabiose⋯Y complexes that the rehybridization is responsible for H-bonds nature either proper or improper.

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The research related to this article was funded by the Algerian Ministry of Higher Education and Scientific Research.

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  1. Laboratoire de Chimie Théorique de Bio- et Nano-Systèmes, Faculté des Sciences Exactes, University Djillali Liabes of Sidi Bel-Abbès, Sidi Bel-abbès, Algeria

    Fodil Rachida & Sekkal-Rahal Majda

  2. ENP Maurice Audin d’Oran, Oran, Algeria

    Fodil Rachida

  3. UCCS - UMR CNRS 8181, Université d’Artois, Faculté des Sciences Jean Perrin, Rue Jean Souvraz, SP 1862307, Lens, France

    Sayede Adlane

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Rachida, F., Adlane, S. & Majda, SR. Theoretical investigation on the improper hydrogen bond in κ-carrabiose⋯Y (Y = HF, HCl, HBr, NH3, H2O, and H2S) complexes. J Mol Model 27, 292 (2021). https://doi.org/10.1007/s00894-021-04904-z

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