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Quantum Chemical Analysis of the Electronic Spectra of Molecular, Ionic, and Zwitterionic forms of 1-Amino- and 1-(N-Phenyl)Aminonaphthalene-8- Sulfonic Acids

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Abstract

Geometric and electronic structures of molecular (AH), cationic \((\text{AH}_{2}^{+})\), zwitterionic (A–H+), and anionic (A–) forms of substituted naphthalenesulfonic (1-aminonaphthalene-8-sulfonic and 1-(N-phenyl)aminonaphthalene-8-sulfonic) acids are considered by the B3LYP DFT method. The theoretical electronic absorption and emission spectra of various forms of the studied sulfonic acids are recorded and analyzed. It is shown on the example of the molecular form of 1-aminonaphthalene-8-sulfonic acid that the absorption bands of conformer I are shifted to the short-wavelength region due to the presence of intramolecular hydrogen bonding, in contrast to the conformers containing no such bonds. The relationship between the energy and shape of frontier orbitals of various forms of sulfonic acids and the features of their electronic absorption spectra is analyzed. It is shown that the theoretical emission spectra of the cationic and zwitterionic forms of 1-(N-phenyl)aminonaphthalene-8-sulfonic acid reproduce well the tendency of the experimental spectra where the band with the maximum wavelength shifts to the long-wavelength region upon the transition from an acidic medium to weakly acidic and neutral ones.

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Funding

This study was funded by the Russian Science Foundation (project No. 22-73-00091, https://rscf.ru/project/22-73-00091/).

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  1. Ivanovo State University, Ivanovo, Russia

    M. S. Fedorov, E. A. Lapykina, N. I. Giricheva & A. A. Filippov

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  1. M. S. Fedorov
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  2. E. A. Lapykina
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Correspondence to M. S. Fedorov.

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Russian Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 8, 114392.https://doi.org/10.26902/JSC_id114392

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Fedorov, M.S., Lapykina, E.A., Giricheva, N.I. et al. Quantum Chemical Analysis of the Electronic Spectra of Molecular, Ionic, and Zwitterionic forms of 1-Amino- and 1-(N-Phenyl)Aminonaphthalene-8- Sulfonic Acids. J Struct Chem 64, 1412–1422 (2023). https://doi.org/10.1134/S0022476623080061

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