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Quantum chemical study on inclusion of linalool into cucurbiturils

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Abstract

Inclusion of one of the natural enantiomers of linalool ((R)-(-)-linalool, simply LIN) into cucurbit[n]urils (CB[n]s) was investigated by means of DFTB + and DFT computations with Grimme’s dispersion correction and geometric counterpoise treatment. Among different cucurbit[n = 5 ~ 9]urils, some diastereoisomers of CB[7] can form relatively stable inclusion complexes (LIN@CB[n]s) with LIN in water. Hydrogen bonds and dispersion interaction between CB[n] and LIN play an important role in formation of the inclusion complexes. Molecular electrostatic potential, non-covalent interaction, and natural bond analysis were carried out for interpretation of stability of the relatively stable LIN@CB[7]s. Theoretical computations showed that LIN@i-CB[7] was the most stable and it can offer increased solubility to linalool in water than the normal CB[7]. The calculated electronic spectra of linalool, i-CB[7], and LIN@i-CB[7] showed that inclusion of linalool into i-CB[7] can be useful in protection of linalool from photo-degradation.

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Author information

Authors and Affiliations

  1. Faculty of Chemistry, Kim Il Sung University, Pyongyang, Democratic People’s Republic of Korea

    Kye-Ryong Sin, Sun-Gyong Ko, Kwang-Ho Pak & Myong-Bok Kim

  2. Faculty of Chemistry, Kim Hyong Jik University of Education, Pyongyang, Democratic People’s Republic of Korea

    Chol-Jin Kim

  3. Faculty of Life Science, Kim Il Sung University, Pyongyang, Democratic People’s Republic of Korea

    Tok-Man Hwang

Authors
  1. Kye-Ryong Sin
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  2. Chol-Jin Kim
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  3. Sun-Gyong Ko
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  4. Tok-Man Hwang
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  5. Kwang-Ho Pak
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  6. Myong-Bok Kim
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Contributions

K.R. Sin designed simulations, C.J. Kim prepared models, S.G. Ko calculated the geometric structures, T.M. Hwang calculated the electronic structures, K.H. Pak discussed NBO analysis, and M.B. Kim wrote the manuscript.

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Correspondence to Kye-Ryong Sin.

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The authors declare no competing interests.

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Faculty of Chemistry, Kim Il Sung University, Ryongnam-Dong, Taesong District, Pyongyang, Democratic People’s Republic of Korea.

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Highlights

• Inclusion complexes of linalool into cucurbiturils in aqueous solution were studied by DFTB + and DFT.

• Inverted CB[7]s can form more stable inclusion complexes than other CB[n]s.

• Hydrogen bond and non-covalent interaction play an important role for inclusion.

Supplementary Information

Below is the link to the electronic supplementary material.

11224_2023_2191_MOESM1_ESM.docx

Supplementary file1 Supplementary data to this article (atomic coordinates , bond length changes, natural populations for LIN@CB[7]s) can be found online at http://dx.doi.org/xxx. (DOCX 374 KB)

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Sin, KR., Kim, CJ., Ko, SG. et al. Quantum chemical study on inclusion of linalool into cucurbiturils. Struct Chem 35, 413–420 (2024). https://doi.org/10.1007/s11224-023-02191-3

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