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dc.contributor.author Minteguiaga, Manuel
dc.contributor.author Dellacassa, Eduardo
dc.contributor.author Iramain, Maximiliano Alberto
dc.contributor.author Catalan, Cesar Atilio Nazareno
dc.contributor.author Brandan, Silvia Antonia
dc.date.available 2018-12-07T13:25:40Z
dc.date.issued 2017-12
dc.identifier.citation Minteguiaga, Manuel; Dellacassa, Eduardo; Iramain, Maximiliano Alberto; Catalan, Cesar Atilio Nazareno; Brandan, Silvia Antonia; A structural and spectroscopic study on carquejol, a relevant constituent of the medicinal plant Baccharis trimera (Less.) DC. (Asteraceae); Elsevier Science; Journal of Molecular Structure; 1150; 12-2017; 8-20
dc.identifier.issn 0022-2860
dc.identifier.uri http://hdl.handle.net/11336/66037
dc.description.abstract Carquejol and its acetate are monoterpenoids based on the rare o-menthane skeleton and distinctive components of the essential oil from Baccharis trimera. Carquejol was characterized by using Fourier Transform infrared (FT-IR) and Raman (FT-Raman), Ultraviolet–Visible (UV–Visible), Electronic Circular Dichroism (ECD), Mass, Hydrogen and Carbon Nuclear Magnetic Resonance (1H and 13C NMR) and 2D 1H–1H gCOSY, 1H–13CgHSQC, 1H–13CgHMBC spectroscopies. Due to the chirality of this monoterpenoid, six different structures were analysed, of which only four showed higher populations and minimal energies. The natural bond orbital (NBO), atoms in molecules (AIM), Merz-Kollman (MK) charges, molecular electrostatic potentials (MEP) and frontier orbitals studies were performed in order to evaluate their structural, electronic, topological and vibrational properties. All calculations were performed by using the hybrid B3LYP method and the 6-31G* and 6-311++G** basis sets. The comparison of the experimental ECD spectra with the corresponding theoretical ones confirm the (4S,5R) configuration assigned to carquejol. The force fields for the most stable configurations were computed by using those two levels of theory and the complete vibrational assignments for the two conformations of carquejol are reported. The different orientations and directions of the dipole moments of the two structures and the proximity in the nucleophilic indexes with those reported for other terpenes could justify in part the potential biological properties reported for carquejol. The MEP surfaces for both structures reveal that the nucleophilic and electrophilic sites of higher reactivity are principally centred on the OH groups.
dc.format application/pdf
dc.language.iso eng
dc.publisher Elsevier Science
dc.rights info:eu-repo/semantics/restrictedAccess
dc.rights.uri https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject BACCHARIS TRIMERA
dc.subject CARQUEJOL
dc.subject DFT CALCULATIONS
dc.subject FORCE FIELD
dc.subject MOLECULAR STRUCTURE
dc.subject VIBRATIONAL SPECTRA
dc.subject.classification Otras Ciencias Químicas
dc.subject.classification Ciencias Químicas
dc.subject.classification CIENCIAS NATURALES Y EXACTAS
dc.title A structural and spectroscopic study on carquejol, a relevant constituent of the medicinal plant Baccharis trimera (Less.) DC. (Asteraceae)
dc.type info:eu-repo/semantics/article
dc.type info:ar-repo/semantics/artículo
dc.type info:eu-repo/semantics/publishedVersion
dc.date.updated 2018-12-05T14:45:28Z
dc.journal.volume 1150
dc.journal.pagination 8-20
dc.journal.pais Países Bajos
dc.journal.ciudad Amsterdam
dc.description.fil Fil: Minteguiaga, Manuel. 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. Universidad de la República; Uruguay
dc.description.fil Fil: Dellacassa, Eduardo. Universidad de la República; Uruguay
dc.description.fil Fil: Iramain, Maximiliano Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; Argentina
dc.description.fil 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
dc.description.fil Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; Argentina
dc.journal.title Journal of Molecular Structure
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1016/j.molstruc.2017.08.068
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286017311365
dc.conicet.fuente Elsevier


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info:eu-repo/semantics/restrictedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)