The eight structures of caffeic acid: a jet-cooled laser ablated rotational study

This work reports a complete conformational analysis of caffeic acid, an exceptionally versatile pharmacophore, using laser ablation chirped-pulse Fourier transform microwave spectroscopy. The whole conformational space consisting of eight distinct species has been fully deciphered based on the tren...

Full description

Saved in:
Bibliographic Details
Published inRSC advances Vol. 13; no. 1; pp. 212 - 219
Main Authors Juárez, G, Sanz-Novo, M, Aguado, R, Alonso, J. L, León, I, Alonso, E. R
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 19.12.2022
The Royal Society of Chemistry
Subjects
Biological activity
Chemistry
Conformational analysis
Fourier transforms
Hydroxycinnamic acid
Laser ablation
Laser cooling
Pharmacology
Rotational spectra
Online AccessGet full text

Cover

More Information
Summary:This work reports a complete conformational analysis of caffeic acid, an exceptionally versatile pharmacophore, using laser ablation chirped-pulse Fourier transform microwave spectroscopy. The whole conformational space consisting of eight distinct species has been fully deciphered based on the trend of the rotational constants supported by theoretical computations. We show how rotational spectroscopy can be confidently used to distinguish between conformers even when the structural differences are minimal, such as those involved in the conformational panorama of caffeic acid. Additionally, the structural information here provided, such as the planarity observed in all the conformers, could help to elucidate the mechanisms underlying the biological and pharmacological activity of hydroxycinnamic acids. This work reports a complete conformational analysis of caffeic acid, an exceptionally versatile pharmacophore, using laser ablation chirped-pulse Fourier transform microwave spectroscopy.
Bibliography:https://doi.org/10.1039/d2ra07124j
Electronic supplementary information (ESI) available: In Section 1 we provide the original LA-CP-FTMW broadband spectrum of caffeic acid (Fig. S1). We collect in Section 2 a complete list of the measured frequencies and residuals (in MHz) for all the observed rotamers of caffeic acid (see Tables S1-S8). Finally, in Section 3 we display the Cartesian coordinates of the caffeic acid conformers optimized at B3LYP-GD3BJ/6-311++G(d, p), which are shown in Tables S9-S16. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra07124j