An ab initio simulation of the UV/Visible spectra of substituted chalcones

• Authors: Yunsheng Xue , Jie Mou , Yi Liu , Xuedong Gong , Yihua Yang , Lin An
• Languages of publication: EN

Abstracts

EN

The electronic absorption spectra of 29 phenyl-ring substituted chalcones have been investigated with the time-dependent density functional theory (TD-DFT) and polarizable continuum TD-DFT (PCM-TD-DFT). It turns out that the hybrid PBE1PBE functional with the 6-31G basis set provide reliable λmax when the solvent effects are included in the model. Comparisons with experimental values lead to a mean absolute error of 12 nm (0.136 eV). Moreover, the observed substituent effects are reproduced by calculation qualitatively. The λmax of substituted chalcone in phenyl ring A is less sensitive to substitution than that in ring B. The linear correlation of Hammett’s substituent constants (σP) with LUMO energies is better with respect to HOMO energies. The calculation reveals that the maximum absorption band mainly results from the π→π* transition from HOMO to LUMO. The analysis of the electron density plots of frontier molecular orbitals show that most transitions should be of valence excitation nature. [...]

Keywords

EN

Chalcones; TD-DFT; PCM; Absorption spectrum; Substituent effect

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 4
• Pages: 928-936

Dates

published

1 - 8 - 2010

online

17 - 6 - 2010

Contributors

author

Yunsheng Xue

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

author

Jie Mou

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

author

Yi Liu

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

author

Xuedong Gong

• Department of Chemistry, Nanjing University of Science and Technology, Nanjing, 210094, China

author

Yihua Yang

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

author

Lin An

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

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Identifiers

DOI

10.2478/s11532-010-0058-3