Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer
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2013
Authors
Banjac, Nebojša R.
Trišović, Nemanja

Vitnik, Željko

Vitnik, Vesna

Valentić, Nataša V.

Ušćumlić, Gordana

Juranić, Ivan

Article (Published version)

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Show full item recordAbstract
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.
Keywords:
Succinimides / Absorption spectra / Solvent effect / Quantum chemical calculationsSource:
Monatshefte Fur Chemie, 2013, 144, 10, 1525-1535Publisher:
- Springer Wien, Wien
Projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1007/s00706-013-1052-1
ISSN: 0026-9247