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.
TY - JOUR
AU - Banjac, Nebojša R.
AU - Trišović, Nemanja
AU - Vitnik, Željko
AU - Vitnik, Vesna
AU - Valentić, Nataša V.
AU - Ušćumlić, Gordana
AU - Juranić, Ivan
PY - 2013
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1173
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
VL - 144
IS - 10
SP - 1525
EP - 1535
DO - 10.1007/s00706-013-1052-1
ER -
@article{
author = "Banjac, Nebojša R. and Trišović, Nemanja and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša V. 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",
volume = "144",
number = "10",
pages = "1525-1535",
doi = "10.1007/s00706-013-1052-1"
}
Banjac, N. R., Trišović, N., Vitnik, Ž., Vitnik, V., Valentić, N. V., 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 NR, Trišović N, Vitnik Ž, Vitnik V, Valentić NV, 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 R., Trišović, Nemanja, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša V., 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 . .
