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Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer

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Abstract

Two series of 1-aryl-3-phenyl- and 1-aryl-3,3-diphenylpyrrolidine-2,5-diones were synthesized and their solvatochromic properties were studied in a set of 15 solvents of different polarity. The effect of specific and non-specific solvent–solute interactions on the position of their absorption bands was evaluated by using the solvent parameter sets of Kamlet and Taft. The interpretation of the effect of different substituent patterns on the solvatochromic properties of the investigated compounds was based on quantum chemical calculations performed by the density functional theory (DFT)/CAM-B3LYP method using the 6-311G(d,p) basis set. The theoretical absorption frequencies show very good agreement with the experimental values. The energy gaps between the HOMO and LUMO orbitals were also analyzed. It is demonstrated that different substituents change the conjugation effect and further determine the pathways of intramolecular charge transfer.

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Notes

  1. Optimized structures of our compounds are of C 1 symmetry (no symmetry elements). Therefore, it is hard to identify clear π or σ orbitals, except for local molecular fragments. By visual inspection most orbitals are of π character on the benzene (phenyl) rings, but for a molecule as a whole it is impossible to define a π-nodal plane. All calculated electron transitions involve several electronic transitions among various pairs of orbitals.

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Acknowledgments

This work was performed within the framework of the research Projects Nos. ON 172013 and 172035, supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia.

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Authors and Affiliations

  1. Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia

    Nebojša Banjac, Nemanja Trišović, Nataša Valentić & Gordana Ušćumlić

  2. Faculty of Chemistry, University of Belgrade, Belgrade, Serbia

    Željko Vitnik

  3. Department of Chemistry, IChTM-Institute of Chemistry, Technology, and Metallurgy, University of Belgrade, Belgrade, Serbia

    Vesna Vitnik & Ivan Juranić

Authors
  1. Nebojša Banjac
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  2. Nemanja Trišović
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  3. Željko Vitnik
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  4. Vesna Vitnik
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  5. Nataša Valentić
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  6. Gordana Ušćumlić
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Correspondence to Gordana Ušćumlić.

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Banjac, N., Trišović, N., Vitnik, Ž. et al. Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer. Monatsh Chem 144, 1525–1535 (2013). https://doi.org/10.1007/s00706-013-1052-1

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  • DOI: https://doi.org/10.1007/s00706-013-1052-1

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