A structural and vibrational study of dehydrofukinone combining FTIR, FTRaman, UV–visible and NMR spectroscopies with DFT calculations

Authors
Lizarraga, Emilio Fernando; Romano, Élida; Raschi, Ana Beatriz; Leyton, Patricio; Paipa, Carolina; Catalan, Cesar Atilio Nazareno; Brandan, Silvia Antonia
Publication Year
2013
Language
English
Format
article
Status
Published version
Description
The vibrational and electronic properties of 4b,5b-eremophil-7(11)9-dien-8-one, also known as dehydrofukinone (DHF), have been investigated by using experimental FT-IR, FT-Raman, NMR and UV spectra techniques and density functional theory (DFT) employing B3LYP exchange correlation with the 6-31G and 6-311++G basis sets. The calculated vibrational frequencies and the chemical shifts were successfully compared with the corresponding experimental values. The DFT calculations were combined with the Pulay’s scaled quantum mechanical force field (SQMFF) methodology in order to perform a complete assignment of the observed bands in the vibrational spectra. The comparison of the theoretical ultraviolet–visible spectrum with the corresponding experimental demonstrates a good concordance. The natural bond orbital (NBO) study reveals for the isopropyliden and the two rings of DHF the characteristics of the electronic delocalization, while the corresponding topological properties of electronic charge density were analyzed by employing Bader’s Atoms in the Molecules theory (AIM).
Fil: Lizarraga, Emilio Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Romano, Élida. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Raschi, Ana Beatriz. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica; Argentina
Fil: Leyton, Patricio. Pontificia Universidad Catolica de Valparaiso; Chile
Fil: Paipa, Carolina. Universidad de Playa Ancha; Chile
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Subject
Dehydrofukinone
Vibrational spectra
Molecular structure
Force field
DFT calculations
Otras Ciencias Químicas
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Restricted access
License
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/26752