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O—H and C—H bond dissociations in non-phenyl and phenyl groups: A DFT study with dispersion and long-range corrections

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Abstract

Hydrogen atom transfer is one important reaction in biological system, in industry, and in atmosphere. The reaction is preluded by hydrogen bond dissociation. To gain a comprehensive understanding on the reaction, it is necessary to investigate how the current computational methods model hydrogen bond dissociation. As a starting point, we utilized density functional theory-based calculations to identify the effect of dispersion and long-range corrections on O—H and C—H dissociations in non-phenyl and phenyl groups. We employed five different methods, namely B3LYP, CAM-B3LYP (with long-range correction), M06-2X, and B3LYP and CAM-B3LYP with the D3 version of Grimme’s dispersion. The results showed that for the case of O—H dissociation in two member of phenyl groups, namely phenol and catechol, the dispersion correction’s effect was negligible, but the long-range correction’s effect was significant. The significant effect was shown by the increasing of energy barrier and the shortening of O—H interatomic distance in the transition state. Therefore, we suggest one should consider the long-range correction in modeling hydrogen bond dissociation in phenolic compounds, namely phenol and catechol.

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Acknowledgements

Authors thank to Rizka Nur Fadilla (Universitas Airlangga, Indonesia) and Prof. Azizan Ahmad (University Kebangsaan Malaysia, Malaysia) for the insightful discussions. LSPB is grateful for the doctoral scholarship by Lembaga Pengelola Dana Pendidikan (LPDP). All calculations using Gaussian 16 software are performed at Riven Cluster, the high-performance computing facility in Research Center for Quantum Engineering Design, Universitas Airlangga, Indonesia.

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Authors and Affiliations

  1. Department of Physics, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya, 60115, Indonesia

    Febdian Rusydi

  2. Research Center for Quantum Engineering Design, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya, 60115, Indonesia

    Lusia Silfia Pulo Boli, Febdian Rusydi, Vera Khoirunisa & Ira Puspitasari

  3. Department of Engineering Physics, Faculty of Industrial Engineering, Institut Teknologi Bandung, Bandung, 40132, Indonesia

    Lusia Silfia Pulo Boli & Hermawan Kresno Dipojono

  4. Engineering Physics Study Program, Institut Teknologi Sumatera, Jl. Terusan Ryacudu, Lampung Selatan, 35365, Indonesia

    Vera Khoirunisa

  5. Information System Study Program, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya, 60115, Indonesia

    Ira Puspitasari

  6. School of Pharmacy, Institut Teknologi Bandung, Jl. Ganesha 10, Bandung, 40132, Indonesia

    Heni Rachmawati

  7. Research Center for Nanoscience and Nanotechnology, Institut Teknologi Bandung, Jl. Ganesha 10, Bandung, 40132, Indonesia

    Heni Rachmawati

Authors
  1. Lusia Silfia Pulo Boli
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  2. Febdian Rusydi
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  3. Vera Khoirunisa
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  6. Hermawan Kresno Dipojono
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Contributions

F.R. contributed to conceptualization; L.S.P.B, H.R., and I.P. contributed to formal analysis; L.S.P.B and V.K. were involved in investigation; F.R. and L.S.P.B contributed to methodology; I.P. provided the resources; L.S.P.B contributed to writing—original draft preparation; F.R. and H.K.D contributed to writing—review and editing. All authors have read and agreed to the published version of the manuscript.

Corresponding author

Correspondence to Febdian Rusydi.

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Funding

This work was supported by Universitas Airlangga under grant scheme Riset Kolaborasi Mitra Luar Negeri 2019 no. 1148/UN3.14/LT/2019 and by Direktorat Riset dan Pengabdian Masyarakat, Deputi Bidang Penguatan Riset dan Pengembangan Kementerian Riset dan Teknologi/Badan Riset dan Inovasi Nasional, Republik Indonesia under grant scheme Penelitian Dasar Unggulan Perguruan Tinggi (PDUPT) 2020 no. 1288r/I1.C06/PL/2020.

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The authors have no conflicts of interest to declare that are relevant to the content of this article.

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Pulo Boli, L.S., Rusydi, F., Khoirunisa, V. et al. O—H and C—H bond dissociations in non-phenyl and phenyl groups: A DFT study with dispersion and long-range corrections. Theor Chem Acc 140, 94 (2021). https://doi.org/10.1007/s00214-021-02781-6

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