Tactfully improve the antioxidant activity of 2'-hydroxychalcone with the strategy of substituent, solvent and intramolecular hydrogen bond effects

被引:15
|
作者
Shang, Changjiao [1 ]
Zhang, Yajie [1 ]
Sun, Chaofan [1 ]
Wang, Lingling [2 ,3 ,4 ]
机构
[1] Northeast Forestry Univ, Coll Sci, Harbin 150040, Peoples R China
[2] Northeast Forestry Univ, Coll Chem Chem Engn & Resource Utilizat, Harbin 150040, Peoples R China
[3] Northeast Forestry Univ, Key Lab Forest Plant Ecol, Minist Educ, Harbin 150040, Peoples R China
[4] Northeast Forestry Univ, Heilongjiang Prov Key Lab Ecol Utilizat Forestry B, Harbin 150040, Peoples R China
关键词
Chalcones; Density functional theory; Antioxidant activity; Intramolecular hydrogen bond; RADICAL SCAVENGING ACTIVITY; PHENOLIC-COMPOUNDS; PROTON-TRANSFER; MECHANISM; CHALCONES; DERIVATIVES; ENTHALPIES; FLAVONOIDS; BEHAVIOR; PATHWAY;
D O I
10.1016/j.molliq.2022.119748
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The substituent and solvent effects on the antioxidant activity of 2'-hydroxychalcone (2'Cha) were sys-tematically explored in gas and three solvent phases by designing six novel compounds (2'Cha-3'NH2, 2'Cha-4'NH2, 2'Cha-5'NH2, 2'Cha-3'CN, 2'Cha-4'CN, and 2'Cha-5'CN) based on the density functional the-ory (DFT) approach. Significant parameters involved in three primary antioxidant mechanisms, namely the hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were computed to confirm the thermodynamically pre-ferred reaction pathway in different media. Besides, 4'-hydroxychalcone (4'Cha) was introduced to unveil the intramolecular hydrogen bond (IHB) effect on the radical scavenging capacity of 2'Cha utilizing the DFT and 2,2-Diphenyl-1-picrylhydrazyl (DPPH) ultraviolet-visible (UV-Vis) spectroscopic methods. Energy barriers and kinetic parameters for HAT reaction of 2'Cha and 4'Cha with hydroperoxyl (HOO?) radical were calculated to further compare the radical-trapping process. The photophysical properties of 2'Cha in benzene, chlorobenzene and ethanol are in good agreement with the measured experimental data and the excited-state antiradical capacity improving mechanism was also confirmed experimentally. The current work not only provides valuable guidance for synthesizing high-efficiency antioxidants but also exploits the potential application fields for 2'Cha. (C) 2022 Elsevier B.V. All rights reserved.
引用
收藏
页数:13
相关论文
共 50 条
  • [1] Substituent effects on the strength of the intramolecular hydrogen bond of thiomalonaldehyde
    González, L
    Mó, O
    Yáñez, M
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2314 - 2321
  • [2] Theoretical and experimental study of a new antioxidant xanthone: Solvent and intramolecular hydrogen bond effects
    dos Santos, N. S. S.
    Barbieri, H. B.
    Pinheiro, M.
    Fill, T. P.
    Queiroz, M. H.
    Pina, J.
    Belo, E.
    Georg, H. C.
    da Cunha, A. R.
    Marinho, P. S. B.
    Marinho, A. M. R.
    Coutinho, K.
    Canuto, S.
    Gester, R.
    JOURNAL OF MOLECULAR LIQUIDS, 2024, 408
  • [3] PCM study of the solvent and substituent effects on the conformers, intramolecular hydrogen bonds and bond dissociation enthalpies of 2-substituted phenols
    Lithoxoidou, AT
    Bakalbassis, EG
    JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (02): : 366 - 377
  • [4] Substituent effects on the isomerization of hydrazone switches driven by the intramolecular hydrogen bond
    Lu, Chaocao
    Htan, Bu
    Fu, Shitao
    Ma, Chunmiao
    Gan, Quan
    TETRAHEDRON, 2019, 75 (30) : 4010 - 4016
  • [5] Influence of intramolecular hydrogen bond on the antioxidant activity of hindered phenols
    Su, Shuo
    Long, Jun
    Duan, Qinghua
    Zhou, Han
    Wu, Zhiqiang
    Zhao, Yi
    Wang, Lihua
    Li, Xinhua
    Shiyou Xuebao, Shiyou Jiagong/Acta Petrolei Sinica (Petroleum Processing Section), 2014, 30 (05): : 772 - 778
  • [6] The Substituent and Solvent Effects on the Antioxidant Activity of the Ferulic Acid Derivations
    Najafi, Meysam
    Bukhari, Shazia Anwer
    Nagra, Saeed Ahmad
    Naqvi, Syed Ali Raza
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2014, 36 (02): : 268 - 276
  • [7] Solvent and substituent effects on the conformational equilibria and intramolecular hydrogen bonding of 4-substituted-2-hydroxybenzaidehydes
    Blanco, Sonia E.
    Ferretti, Ferdinando H.
    TETRAHEDRON LETTERS, 2007, 48 (14) : 2577 - 2581
  • [8] In Silico Study of Solvent Effects on the Intramolecular Hydrogen Bond of Hydroxy Proline
    Cotua, Jose
    Cotes, Sandra
    ORIENTAL JOURNAL OF CHEMISTRY, 2022, 38 (03) : 676 - 680
  • [9] A theoretical study of solvent effects on the characteristics of the intramolecular hydrogen bond in Droxidopa
    Yoosefian, Mehdi
    Karimi-Maleh, Hassan
    Sanati, Afsaneh L.
    JOURNAL OF CHEMICAL SCIENCES, 2015, 127 (06) : 1007 - 1013
  • [10] A theoretical study of solvent effects on the characteristics of the intramolecular hydrogen bond in Droxidopa
    MEHDI YOOSEFIAN
    HASSAN KARIMI-MALEH
    AFSANEH L SANATI
    Journal of Chemical Sciences, 2015, 127 : 1007 - 1013