Spectroscopic (FT-IR, FT-Raman, 1H- and 13C-NMR), Theoretical and Microbiological Study of trans o-Coumaric Acid and Alkali Metal o-Coumarates

Molecules

Małgorzata Kowczyk-Sadowy¹  Renata Świsłocka¹  Hanna Lewandowska²  Jolanta Piekut¹  Włodzimierz Lewandowski¹ 

[1] Division of Chemistry, Bialystok University of Technology, Wiejska 45E, Bialystok 15-351, Poland; E-Mails:;Institute of Nuclear Chemistry and Technology, 16 Dorodna St., Warsaw 03-195, Poland; E-Mail:

关键词: 2-hydroxycinnamic acid;    alkali metal o-coumarates;    FT-IR;    FT-Raman;    NMR;    antimicrobial activity;   

DOI  :  10.3390/molecules20023146

来源: mdpi

【 摘 要 】

This work is a continuation of research on a correlation between the molecular structure and electronic charge distribution of phenolic compounds and their biological activity. The influence of lithium, sodium, potassium, rubidium and cesium cations on the electronic system of trans o-coumaric (2-hydroxy-cinnamic) acid was studied. We investigated the relationship between the molecular structure of the tested compounds and their antimicrobial activity. Complementary molecular spectroscopic techniques such as infrared (FT-IR), Raman (FT-Raman), ultraviolet-visible (UV-VIS) and nuclear magnetic resonance (¹H- and ¹³C-NMR) were applied. Structures of the molecules were optimized and their structural characteristics were calculated by the density functional theory (DFT) using the B3LYP method with 6-311++G** as a basis set. Geometric and magnetic aromaticity indices, atomic charges, dipole moments and energies were also calculated. Theoretical parameters were compared to the experimental characteristics of investigated compounds. Correlations between certain vibrational bands and some metal parameters, such as electronegativity, ionization energy, atomic and ionic radius, were found. The microbial activity of studied compounds was tested against Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris and Candida albicans.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.