Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy

Autores
Piro, Oscar Enrique; Echeverria, Gustavo Alberto; Lizarraga, Emilio Fernando; Romano, Elida; Catalan, Cesar Atilio Nazareno; Brandán, Silvia Antonia
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The molecular structure of two mixed and closely related conformers of the title compound, C13H16O2, found in the solid with unequal occupancies has been determined by X-ray diffraction methods. The substance crystallizes in the monoclinic Pca21 space group with a=17.279(2), b=5.1716(7), c=12.549(2) Å, and Z=4 molecules per unit cell. The structure was solved from 1314 reflections with I>2(I) and refined to an agreement R1-factor of 0.049. The minor conformer (34.7%) is nearly mirror-related to and extensively overlapped with the major one. The skeleton of the 4-hydroxyacetophenone molecular fragment and the prenyl group, ?(CH2)-(CH)=C(CH3)2, pendant arm attached to it are both planar and perpendicular to each other. A strong intermolecular O-H?O bond links neighboring molecules in the lattice to produce a polymeric structure. The conformational structures of the compound in the gas phase have been calculated by the DFT method and the geometrical results have been compared with the X-ray data. These data allow a complete assignment of vibration modes in the solid state FTIR and Raman spectra. The calculated 1H and 13C chemicals shifts are in good agreement with the corresponding experimental NMR spectra of the compound in solution.
Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Física la Plata; Argentina
Fil: Echeverria, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Física la Plata; Argentina
Fil: Lizarraga, Emilio Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Brandán, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
Materia
4-Hydroxy-3-(3-Methyl-2-Butenyl) Acetophenone
Vibrational Spectra
Molecular Structure
Force Field
Dft Calculations
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/7814
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/7814
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopyPiro, Oscar EnriqueEcheverria, Gustavo AlbertoLizarraga, Emilio FernandoRomano, ElidaCatalan, Cesar Atilio NazarenoBrandán, Silvia Antonia4-Hydroxy-3-(3-Methyl-2-Butenyl) AcetophenoneVibrational SpectraMolecular StructureForce FieldDft Calculationshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The molecular structure of two mixed and closely related conformers of the title compound, C13H16O2, found in the solid with unequal occupancies has been determined by X-ray diffraction methods. The substance crystallizes in the monoclinic Pca21 space group with a=17.279(2), b=5.1716(7), c=12.549(2) Å, and Z=4 molecules per unit cell. The structure was solved from 1314 reflections with I>2(I) and refined to an agreement R1-factor of 0.049. The minor conformer (34.7%) is nearly mirror-related to and extensively overlapped with the major one. The skeleton of the 4-hydroxyacetophenone molecular fragment and the prenyl group, ?(CH2)-(CH)=C(CH3)2, pendant arm attached to it are both planar and perpendicular to each other. A strong intermolecular O-H?O bond links neighboring molecules in the lattice to produce a polymeric structure. The conformational structures of the compound in the gas phase have been calculated by the DFT method and the geometrical results have been compared with the X-ray data. These data allow a complete assignment of vibration modes in the solid state FTIR and Raman spectra. The calculated 1H and 13C chemicals shifts are in good agreement with the corresponding experimental NMR spectra of the compound in solution.Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Física la Plata; ArgentinaFil: Echeverria, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Física la Plata; ArgentinaFil: Lizarraga, Emilio Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; ArgentinaFil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; ArgentinaFil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; ArgentinaFil: Brandán, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; ArgentinaElsevier2013-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/7814Piro, Oscar Enrique; Echeverria, Gustavo Alberto; Lizarraga, Emilio Fernando; Romano, Elida; Catalan, Cesar Atilio Nazareno; et al.; Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy; Elsevier; Spectrochimica Acta A: Molecular And Biomolecular Spectroscopy; 101; 1-2013; 196-2030584-8539enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1386142512009729info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2012.09.086info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:15:27Zoai:ri.conicet.gov.ar:11336/7814instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 15:15:27.8CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
title Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
spellingShingle Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
Piro, Oscar Enrique
4-Hydroxy-3-(3-Methyl-2-Butenyl) Acetophenone
Vibrational Spectra
Molecular Structure
Force Field
Dft Calculations
title_short Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
title_full Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
title_fullStr Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
title_full_unstemmed Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
title_sort Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy
dc.creator.none.fl_str_mv Piro, Oscar Enrique
Echeverria, Gustavo Alberto
Lizarraga, Emilio Fernando
Romano, Elida
Catalan, Cesar Atilio Nazareno
Brandán, Silvia Antonia
author Piro, Oscar Enrique
author_facet Piro, Oscar Enrique
Echeverria, Gustavo Alberto
Lizarraga, Emilio Fernando
Romano, Elida
Catalan, Cesar Atilio Nazareno
Brandán, Silvia Antonia
author_role author
author2 Echeverria, Gustavo Alberto
Lizarraga, Emilio Fernando
Romano, Elida
Catalan, Cesar Atilio Nazareno
Brandán, Silvia Antonia
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 4-Hydroxy-3-(3-Methyl-2-Butenyl) Acetophenone
Vibrational Spectra
Molecular Structure
Force Field
Dft Calculations
topic 4-Hydroxy-3-(3-Methyl-2-Butenyl) Acetophenone
Vibrational Spectra
Molecular Structure
Force Field
Dft Calculations
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The molecular structure of two mixed and closely related conformers of the title compound, C13H16O2, found in the solid with unequal occupancies has been determined by X-ray diffraction methods. The substance crystallizes in the monoclinic Pca21 space group with a=17.279(2), b=5.1716(7), c=12.549(2) Å, and Z=4 molecules per unit cell. The structure was solved from 1314 reflections with I>2(I) and refined to an agreement R1-factor of 0.049. The minor conformer (34.7%) is nearly mirror-related to and extensively overlapped with the major one. The skeleton of the 4-hydroxyacetophenone molecular fragment and the prenyl group, ?(CH2)-(CH)=C(CH3)2, pendant arm attached to it are both planar and perpendicular to each other. A strong intermolecular O-H?O bond links neighboring molecules in the lattice to produce a polymeric structure. The conformational structures of the compound in the gas phase have been calculated by the DFT method and the geometrical results have been compared with the X-ray data. These data allow a complete assignment of vibration modes in the solid state FTIR and Raman spectra. The calculated 1H and 13C chemicals shifts are in good agreement with the corresponding experimental NMR spectra of the compound in solution.
Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Física la Plata; Argentina
Fil: Echeverria, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Física la Plata; Argentina
Fil: Lizarraga, Emilio Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Brandán, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
description The molecular structure of two mixed and closely related conformers of the title compound, C13H16O2, found in the solid with unequal occupancies has been determined by X-ray diffraction methods. The substance crystallizes in the monoclinic Pca21 space group with a=17.279(2), b=5.1716(7), c=12.549(2) Å, and Z=4 molecules per unit cell. The structure was solved from 1314 reflections with I>2(I) and refined to an agreement R1-factor of 0.049. The minor conformer (34.7%) is nearly mirror-related to and extensively overlapped with the major one. The skeleton of the 4-hydroxyacetophenone molecular fragment and the prenyl group, ?(CH2)-(CH)=C(CH3)2, pendant arm attached to it are both planar and perpendicular to each other. A strong intermolecular O-H?O bond links neighboring molecules in the lattice to produce a polymeric structure. The conformational structures of the compound in the gas phase have been calculated by the DFT method and the geometrical results have been compared with the X-ray data. These data allow a complete assignment of vibration modes in the solid state FTIR and Raman spectra. The calculated 1H and 13C chemicals shifts are in good agreement with the corresponding experimental NMR spectra of the compound in solution.
publishDate 2013
dc.date.none.fl_str_mv 2013-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/7814
Piro, Oscar Enrique; Echeverria, Gustavo Alberto; Lizarraga, Emilio Fernando; Romano, Elida; Catalan, Cesar Atilio Nazareno; et al.; Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy; Elsevier; Spectrochimica Acta A: Molecular And Biomolecular Spectroscopy; 101; 1-2013; 196-203
0584-8539
url http://hdl.handle.net/11336/7814
identifier_str_mv Piro, Oscar Enrique; Echeverria, Gustavo Alberto; Lizarraga, Emilio Fernando; Romano, Elida; Catalan, Cesar Atilio Nazareno; et al.; Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy; Elsevier; Spectrochimica Acta A: Molecular And Biomolecular Spectroscopy; 101; 1-2013; 196-203
0584-8539
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1386142512009729
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2012.09.086
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
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dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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