Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer
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2013
Authors
Banjac, NebojšaTrišović, Nemanja
Vitnik, Željko
Vitnik, Vesna
Valentić, Nataša
Ušćumlić, Gordana
Juranić, Ivan
Article (Published version)
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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
Funding / 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
WoS: 000324589300010
Scopus: 2-s2.0-84885320419
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Banjac, Nebojša AU - Trišović, Nemanja AU - Vitnik, Željko AU - Vitnik, Vesna AU - Valentić, Nataša AU - Ušćumlić, Gordana AU - Juranić, Ivan PY - 2013 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2458 AB - 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. PB - Springer Wien, Wien T2 - Monatshefte Fur Chemie T1 - Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer EP - 1535 IS - 10 SP - 1525 VL - 144 DO - 10.1007/s00706-013-1052-1 ER -
@article{ author = "Banjac, Nebojša and Trišović, Nemanja and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša and Ušćumlić, Gordana and Juranić, Ivan", year = "2013", 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.", publisher = "Springer Wien, Wien", journal = "Monatshefte Fur Chemie", title = "Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer", pages = "1535-1525", number = "10", volume = "144", doi = "10.1007/s00706-013-1052-1" }
Banjac, N., Trišović, N., Vitnik, Ž., Vitnik, V., Valentić, N., Ušćumlić, G.,& Juranić, I.. (2013). Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer. in Monatshefte Fur Chemie Springer Wien, Wien., 144(10), 1525-1535. https://doi.org/10.1007/s00706-013-1052-1
Banjac N, Trišović N, Vitnik Ž, Vitnik V, Valentić N, Ušćumlić G, Juranić I. Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer. in Monatshefte Fur Chemie. 2013;144(10):1525-1535. doi:10.1007/s00706-013-1052-1 .
Banjac, Nebojša, Trišović, Nemanja, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša, Ušćumlić, Gordana, Juranić, Ivan, "Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer" in Monatshefte Fur Chemie, 144, no. 10 (2013):1525-1535, https://doi.org/10.1007/s00706-013-1052-1 . .