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Non-covalent interactions in the monohydrated complexes of 1,2,3,4–tetrahydroisoquinoline

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Abstract

The eleven monohydrates of 1, 2, 3, 4-tetrahydroisoquinoline (THIQ) are analyzed through natural bond orbital (NBO) analysis and QTAIM methods employing M06-2X functional in DFT and MP2 methods. Here, the role of OH bonds as an acceptor and donor is critically analyzed. The role of lone pairs of O is critically monitored in two of the complexes, where N–H···O hydrogen bonds are present. The relative contributions of rehybridisation and hyperconjugation are compared in detail. Popelier criteria are satisfied in all the complexes barring a few exceptions involving weak hydrogen bonds. At the bond critical points (BCP), four monohydrates show higher values of electron density (ρC) and negative values of total electron energy density (HC), while Laplacian \({(\nabla }^{2}{\uprho }_{\mathrm{C}} )\) remains positive. These complexes satisfy the criteria of partial covalency. All these are O–H⋅⋅⋅N-type bonds. Remaining h-bonds are weaker in nature. These are also confirmed by the smaller values of ρC at the respective BCP. The variation of potential energy density (VC) among the complexes seems to be the most important factor in determining the nature of non-covalent interactions.

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Acknowledgements

AC gratefully acknowledges the support received from University Grants Commission through a research Project (F. No. 37-560/2009(SR)) for conducting this work. The authors also acknowledge the instrumental support from DST (Govt. of India) under the departmental FIST programme of the University of Burdwan (Grant no: SR/FST/PS-II-/2018/52(C)) and University Grants Commission (UGC) for departmental CAS (Grant no. F.530/20/CAS-II/2018(SAP-I)) scheme.

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  1. Department of Physics, Government General Degree College, Hooghly, Singur, 712409, India

    Santu Das

  2. Department of Physics, The University of Burdwan, Golapbag Campus, Burdwan, 713104, West Bengal, India

    Santu Das & Abhijit Chakraborty

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Santu Das: literature survey, editing, software handling, data handling, presentation of figures. Abhijit Chakraborty: conceptualisation and visualisation of the problem, writing, reviewing and editing the manuscript, literature survey.

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Das, S., Chakraborty, A. Non-covalent interactions in the monohydrated complexes of 1,2,3,4–tetrahydroisoquinoline. J Mol Model 29, 37 (2023). https://doi.org/10.1007/s00894-022-05438-8

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