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Combined experimental and computational investigation of a Schiff base derived from N-(1-naphthyl)ethylenediamine for fluoride recognition

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Abstract

The Bratton–Marshall reagent, a free base of N-(1-naphthyl)ethylenediamine dihydrochloride (NEDA2+.2Cl−), is used to analyse arylamine type of drugs and as a sensor of many ions/molecules. The Schiff bases of it have also been used as chemosensors for various ions. The Schiff base, N-[2-[3,4-dimethoxybenzylidene)amino]ethyl](1-naphthyl)amine (LH), the condensation product of N-(1-naphthyl)ethylenediamine dihydrochloride and veratraldehyde was thus synthesized and employed for fluoride ion recognition. The compound was characterized using single crystal X-ray diffraction study and spectroscopy methods including UV–Vis, IR, and NMR spectroscopy. The compound crystallizes in orthorhombic system space group P212121 and possesses syn-configuration about the azomethine (–CH=N–) bond. Both the IR (υstr, 1638 cm−1) and NMR (δCH, 8.26 ppm) data evidence that this functionality (–CH=N–) exists in LH. When excited at 370 nm, the compound LH exhibits a prime emission band at 442 nm. It has an –N–H group which can donate proton. It was thus effectively employed for recognizing fluoride ions in DMSO forming L–H…..F− association complex. The value of the association constant (KA) is found to be 1.92 × 103 M−1. The detection and quantification limits of LH for fluoride ions are 9.4 μM and 31.2 μM, respectively. It is significantly lower than the WHO permissible limit, 78.94 μM. DFT and TD-DFT calculations provide a clear understanding of the experimental observations.

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Acknowledgements

The authors gratefully acknowledge the support of the Department of Chemistry, NIT Agartala, for experimental, theoretical and instrumental facilities. ND is thankful to NIT Agartala for receiving Institutional Fellowship for research.

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  1. Department of Chemistry, National Institute of Technology Agartala, Agartala, Tripura, 799046, India

    Nishan Das, Payel Debnath, Nishithendu Bikash Nandi, Atanu Purkayastha, Susanta Ghanta & Tarun Kumar Misra

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  1. Nishan Das
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  2. Payel Debnath
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  3. Nishithendu Bikash Nandi
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Correspondence to Susanta Ghanta or Tarun Kumar Misra.

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706_2023_3111_MOESM1_ESM.docx

Supplementary file1 The CCDC number 2244898 for LH has crystallographic supplementary data and can be obtained without paying any charge from http://www.ccdc.cam.ac.uk/conts/retrieving.html, or the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk. The IR spectra of N-(1-naphthyl)ethylenediamine dihydrochloride and LH are shown in Fig. S1 and S2, respectively. The 13C NMR spectrum of LH is placed in Fig. S3. The optimized structure of LH is given in Fig. S4. The bond lengths and bond angles of LH are listed in Table S1 and S2. The complete theoretical NMR data are listed in Table S3. The Cartesian coordinates (in Angstroms) of the LH molecule and LH...X- (X= F, Cl, Br, I, NO3, OH, HSO4, and OAc) complexes are given in Table S4 – S12 (DOCX 597 KB)

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Das, N., Debnath, P., Nandi, N.B. et al. Combined experimental and computational investigation of a Schiff base derived from N-(1-naphthyl)ethylenediamine for fluoride recognition. Monatsh Chem 154, 1101–1114 (2023). https://doi.org/10.1007/s00706-023-03111-1

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