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Antiradical Properties of trans-2-(4-substituted-styryl)-thiophene.

Authors
  • Gusain, Anamika1
  • Kumar, Naresh1
  • Kumar, Jagdeep1
  • Pandey, Gunjan1
  • Hota, Prasanta Kumar2
  • 1 Department of Chemistry, School of Sciences, Hemvati Nandan Bahuguna Garhwal University, Srinagar (Garhwal), Uttarakhand, 246174, India. , (India)
  • 2 Department of Chemistry, School of Sciences, Hemvati Nandan Bahuguna Garhwal University, Srinagar (Garhwal), Uttarakhand, 246174, India. [email protected] , (India)
Type
Published Article
Journal
Journal of Fluorescence
Publisher
Springer-Verlag
Publication Date
Oct 14, 2020
Identifiers
DOI: 10.1007/s10895-020-02629-5
PMID: 33057974
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

2-substituted thiophene compounds with electron donating and electron withdrawing p-phenyl substitution were synthesized and studied their radical scavenging properties using DPPH assay and DFT method. It is shown that p-hydroxy and p-amino phenyl substituted compound exhibit radical scavenging activity. From DFT and radical scavenging studies, a correlation between IC50 with the bond dissociation enthalpy, proton affinity, ground state dipole moment and optical band gap of compound is found. Compounds 1-3 with electron withdrawing substituent (NO2, CN, Cl) do not show any radical scavenging properties, whereas compounds 6-7 with electron donating substituent (OH, NH2) show antiradical properties. Further, the antiradical activity is reduced drastically by replacing the -OH and -NH2 with methoxy and -N-alkylating group respectively in 6 and 7. The compound with p-hydroxy phenyl substitution, exhibits stronger antiradical activity as compared to the p-amino phenyl substitution due to smaller O-H bond dissociation energy as compared to the N-H bond. From DPPH and DFT studies, it is suggested that the radical scavenging activity in 2-substituted thiophene is occurred through proton transfer mechanism. The other possible SET, SPLET mechanisms are also corroborated. Graphical Abstract Antiradical properties of trans-2-(4-substituted-styryl)-thiophene Anamika Gusain, Naresh Kumar, Jagdeep Kumar, Gunjan Pandey, Prasanta Kumar Hota.

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