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Robustness of hydrogen bonding in the construction of supramolecular architectures in protonated perchlorate salts

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Abstract

Five new multicomponent salts of perchloric acid with a series of substituted anilines and N-heterocyclic amines namely Diphenylaminium perchlorate (DPAPC) (1), 2, 5-dichloroanilinium perchlorate (25DAP) hydrate (2), 4-Methylanilinium perchlorate (4MAPC) (3), 4-diamino-6-methyl-1, 3, 5-triazin-1-ium hydrogen perchlorate (24DAMTHP) (4), and 8-hydroxyquinolinium hydrogen perchlorate (8HQP) (5) were prepared and structurally characterized. The entire complexes were subjected to FTIR and elemental analysis. A vast family of intermolecular contacts N–H…O, O–H…O, N–H…N, and C-H…O was observed, which are key ingredient in the generation of privileged supramolecular self-assemblies appeared as one-dimensional chain, two-dimensional ladder, and helix. Cambridge Structural Database (CSD) analysis of 52 hits revealed the perchloric acid display higher propensity of ladder architectures. Molecular stability of the complexes was studied by quantum chemical calculations using DFT/B3LYP method with 6-31G(d,p) basis set. Furthermore, their relative charge distributions were identified using molecular electrostatic potential map. The use of Hirshfeld surfaces in combination with fingerprint plots was visualized in order to study the closer contacts within the molecule. The relative contribution of the whole percentage of interactions associated is highlighted.

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Data Availability

Crystallographic data of the structure reported in this article have been deposited in the Cambridge Crystallographic Data Centre. The deposition numbers are CCDC-1409707–1,409,711. Copy of the data can be downloaded at free charge from CCDC website (www.ccdc.cam.ac.uk). Experimental and theoretical bond length and angles were tabulated in the Supplementary article.

Code availability

The calculations were performed using Gaussian 09 W and GaussView 5.0 and Hirshfeld surface analysis were done using Crystal Explorer.

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Acknowledgements

The authors thank SAIF, IIT Madras for the Single crystal X-ray diffraction facility.

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Authors and Affiliations

  1. Department of Physics, Anna University, Chennai, India

    D. Sathya, N. Karthikeyan & R. Jagan

  2. Department of Physics, Quiad-E Millath College for Women, Chennai, India

    R. Padmavathy

  3. Department of Physics, University V.O.C. College of Engineering, Anna University, Tuticorin, India

    K. Saminathan

  4. Faculty of Science, Aksheyaa College of Arts and Science, Puludivakkam, Madhuranthagam, India

    R. Akilan

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  1. D. Sathya
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  2. N. Karthikeyan
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  3. R. Padmavathy
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  4. R. Jagan
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  5. K. Saminathan
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  6. R. Akilan
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Contributions

Experimental work, data interpretation, and article writing: DS, NK, RP; editing and discussion: RJ and KS; final review: RA.

Corresponding author

Correspondence to N. Karthikeyan.

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Sathya, D., Karthikeyan, N., Padmavathy, R. et al. Robustness of hydrogen bonding in the construction of supramolecular architectures in protonated perchlorate salts. J Mol Model 28, 74 (2022). https://doi.org/10.1007/s00894-022-05064-4

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