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Impact of gases on the planarity of alkyl-substituted α-oligofuran: DFT study

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Abstract

By using the density functional theory, extensive calculations were performed at the M06-2X/6-311G(d,p) level of theory to assess the impact of different gaseous molecules (H2O, CH3OH, N2H4, H2O2, HCN, NH3, SO2, and CO2) on the planarity of alkyl-substituted α-oligofurans (AOF). Of the eight gases, the greatest planarity distortion of AOF was observed with H2O (P = 0.88), CH3OH (P = 0.91), CO2 (P = 0.93), SO2 (P = 0.94), and H2O2 (P = 0.94) when interacting with AOF on ring 1. When the gases interacted with AOF on ring 2, the planarity remained unchanged. The gases that disrupt the planarity of AOF exhibited a stronger interaction with AOF on ring 1 compared to ring 2. A natural bond orbital (NBO) analysis was conducted to examine the interactions between the gases and AOF on rings 1 and 2. The non-covalent interaction (NCI) analysis revealed that weak van der Waals interactions between Furan rings and alkyl chains in isolated AOF maintain their planarity. These interactions remain uninterrupted when the gases interact with ring 2 of AOF, thus preserving its planarity. However, when the gases interacted with ring 1 of AOF, the van der Waals interactions were disrupted, resulting in a distortion of the planarity.

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Funding

This research was supported by the Brain Pool Program funded by the Ministry of Science and ICT through the National Research Foundation of Korea (2019H1D3A2A01102769).

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Authors and Affiliations

  1. Department of Chemistry, Jagannath University, Dhaka, 1100, Bangladesh

    Joyanta K. Saha & Jahir Raihan

  2. Centre for Advanced Research in Sciences (CARS), Dhaka University, Dhaka, 1000, Bangladesh

    Mohammad Abdul Matin

  3. Department of Nanoenergy Engineering, Pusan National University, Busan, 46241, Korea

    Joonkyung Jang

Authors
  1. Joyanta K. Saha
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  2. Jahir Raihan
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  3. Mohammad Abdul Matin
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  4. Joonkyung Jang
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Contributions

Joyanta K. Saha: conceptualization, methodology, writing original draft preparation; Jahir Raihan: data curation, writing draft; Mohammad Abdul Matin: reviewing and editing; Joonkyung Jang: reviewing and editing.

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Correspondence to Joyanta K. Saha or Joonkyung Jang.

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Saha, J.K., Raihan, J., Matin, M.A. et al. Impact of gases on the planarity of alkyl-substituted α-oligofuran: DFT study. Struct Chem 35, 297–304 (2024). https://doi.org/10.1007/s11224-023-02186-0

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