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A theoretical assignment on excited-state intramolecular proton transfer mechanism for quercetin
Yang, Dapeng1,3; Yang, Guang2; Zhao, Jinfeng3; Zheng, Rui1; Wang, Yusheng1; Lv, Jian1
KeywordAim Esipt Ir Vibrational Spectra Mos Potential Energy Curves
Source PublicationJOURNAL OF PHYSICAL ORGANIC CHEMISTRY
2017-11-01
DOI10.1002/poc.3684
Volume30Issue:11
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic ; Chemistry, Physical
WOS Research AreaChemistry
WOS KeywordDENSITY-FUNCTIONAL THEORY ; HYDROGEN-BONDING DYNAMICS ; PIGMENT YELLOW 101 ; ANISOTROPIC DIELECTRICS ; FLUORESCENCE PROBE ; SENSING MECHANISM ; ELECTRON-DENSITY ; CHARGE-TRANSFER ; ACID SYSTEM ; TD-DFT
AbstractIn the present work, we investigate a new chromophore (ie, quercetin) (Simkovitch et al J Phys Chem B 119 [2015] 10244) about its complex excited-state intramolecular proton transfer (ESIPT) process based on density functional theory and time-dependent density functional theory methods. On the basis of the calculation of electron density rho(r) and Laplacian del(2)rho(r) at the bond critical point using atoms-in-molecule theory, the intramolecular hydrogen bonds (O-1-H2 center dot center dot center dot O5 and O-3-H4 center dot center dot center dot O5) have been supported to be formed in the S-0 state. Comparing the prime structural variations of quercetin involved in its 2 intramolecular hydrogen bonds, we find that these 2 hydrogen bonds should be strengthened in the S-1 state, which is a fundamental precondition for facilitating the ESIPT process. Concomitantly, infrared vibrational spectra analysis further verifies this viewpoint. In good agreement with previous experimental spectra results, we find that quercetin reveals 2 kinds of excited-state structures (quercetin* and quercetin-PT1*) in the S-1 state. Frontier molecular orbitals depict the nature of electronically excited state and support the ESIPT reaction. Our scanned potential energy curves according to variational O-1-H-2 and O-3-H-4 coordinates demonstrate that the proton transfer process should be more likely to occur in the S-1 state via hydrogen bond wire O-1-H2 center dot center dot center dot O5 rather than O-3-H4 center dot center dot center dot O5 because of the lower potential energy barrier 2.3kcal/mol. Our present work explains previous experimental result and makes up the deficiency of mechanism in previous experiment. In the end, we make a reasonable assignment for ESIPT process of quercetin.
Language英语
WOS IDWOS:000412844400004
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/150229
Collection中国科学院大连化学物理研究所
Affiliation1.North China Univ Water Resources & Elect Power, Coll Math & Informat Sci, Zhengzhou 450045, Henan, Peoples R China
2.Jiaozuo Univ, Dept Basic Sci, Jiaozuo 454000, Peoples R China
3.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam Theoret & Computat, Dalian 116023, Peoples R China
Recommended Citation
GB/T 7714
Yang, Dapeng,Yang, Guang,Zhao, Jinfeng,et al. A theoretical assignment on excited-state intramolecular proton transfer mechanism for quercetin[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,2017,30(11).
APA Yang, Dapeng,Yang, Guang,Zhao, Jinfeng,Zheng, Rui,Wang, Yusheng,&Lv, Jian.(2017).A theoretical assignment on excited-state intramolecular proton transfer mechanism for quercetin.JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,30(11).
MLA Yang, Dapeng,et al."A theoretical assignment on excited-state intramolecular proton transfer mechanism for quercetin".JOURNAL OF PHYSICAL ORGANIC CHEMISTRY 30.11(2017).
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