Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol

Autores
Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Structural, electronic, topological and vibrational propertiesof Eucalyptol have been theoretically studied in the gas phaseand in acetone, chloroform, ethanol, and water solutions byusing the hybrid B3LYP/6-31G* level of theory. Theproperties were evaluated in function of the solvent´spermittivities. A higher dipole moment and lower volumevalues were observed for eucalyptol in water due probably tothe higher permittivity. Also, higher corrected solvationenergy is predicted for eucalyptol in water (-22.51 kJ/mol) inagreement with the higher volume contraction observed inthis medium (-0.4 Å3). Atomic charges reveal the mostnegative values on the O atoms and the most positive valueson the C3 and C4 atoms. MEP surfaces of eucalyptol in allmedia evidence clear nucleophilic sites on the O atoms. NBO analyses show two E→* and ELP→* transitions while theAIM studies reveal two new H---H interactions which supportvisibly the stabilities of eucalyptol in all studied media. Thegap values show a decreasing in the reactivity of eucalyptol ingas phase and mainly in chloroform and acetone solutionswhile in aqueous solution eucalyptol is slightly most reactive.Besides, the higher nucleophilic indexes of eucalyptol in allsolvents support the characteristic nucleophilic of eucalyptol,as compared with scopolamine and tropane alkaloids. Theharmonic force fields and their complete vibrationalassignments of 81 normal vibration modes were performed.The predicted IR, ATR, Raman, 1H- and 13C-NMR and UVvisiblespectra show reasonable concordance with thecorresponding experimental ones.
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Materia
EUCALYPTOL
VIBRATIONAL
SPECTRA
STRUCTURAL
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:11336/119324
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/119324
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Effect of Media on the Properties of Monoterpene Cyclic EucalyptolIramain, Maximiliano AlbertoRuiz Hidalgo, JoséBrandan, Silvia AntoniaEUCALYPTOLVIBRATIONALSPECTRASTRUCTURALhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Structural, electronic, topological and vibrational propertiesof Eucalyptol have been theoretically studied in the gas phaseand in acetone, chloroform, ethanol, and water solutions byusing the hybrid B3LYP/6-31G* level of theory. Theproperties were evaluated in function of the solvent´spermittivities. A higher dipole moment and lower volumevalues were observed for eucalyptol in water due probably tothe higher permittivity. Also, higher corrected solvationenergy is predicted for eucalyptol in water (-22.51 kJ/mol) inagreement with the higher volume contraction observed inthis medium (-0.4 Å3). Atomic charges reveal the mostnegative values on the O atoms and the most positive valueson the C3 and C4 atoms. MEP surfaces of eucalyptol in allmedia evidence clear nucleophilic sites on the O atoms. NBO analyses show two E→* and ELP→* transitions while theAIM studies reveal two new H---H interactions which supportvisibly the stabilities of eucalyptol in all studied media. Thegap values show a decreasing in the reactivity of eucalyptol ingas phase and mainly in chloroform and acetone solutionswhile in aqueous solution eucalyptol is slightly most reactive.Besides, the higher nucleophilic indexes of eucalyptol in allsolvents support the characteristic nucleophilic of eucalyptol,as compared with scopolamine and tropane alkaloids. Theharmonic force fields and their complete vibrationalassignments of 81 normal vibration modes were performed.The predicted IR, ATR, Raman, 1H- and 13C-NMR and UVvisiblespectra show reasonable concordance with thecorresponding experimental ones.Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaIJSRM2019-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/119324Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia; Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol; IJSRM; International Journal of Science and Research Methodology; 12; 3; 5-2019; 1-322454-2008CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://ijsrm.humanjournals.com/wp-content/uploads/2019/06/8.Maximiliano-A.-Iramain-Jos%C3%A9-Ruiz-Hidalgo-Silvia-Antonia-Brand%C3%A1n.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:05:14Zoai:ri.conicet.gov.ar:11336/119324instacron: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:34982025-09-03 10:05:14.995CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
title Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
spellingShingle Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
Iramain, Maximiliano Alberto
EUCALYPTOL
VIBRATIONAL
SPECTRA
STRUCTURAL
title_short Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
title_full Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
title_fullStr Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
title_full_unstemmed Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
title_sort Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol
dc.creator.none.fl_str_mv Iramain, Maximiliano Alberto
Ruiz Hidalgo, José
Brandan, Silvia Antonia
author Iramain, Maximiliano Alberto
author_facet Iramain, Maximiliano Alberto
Ruiz Hidalgo, José
Brandan, Silvia Antonia
author_role author
author2 Ruiz Hidalgo, José
Brandan, Silvia Antonia
author2_role author
author
dc.subject.none.fl_str_mv EUCALYPTOL
VIBRATIONAL
SPECTRA
STRUCTURAL
topic EUCALYPTOL
VIBRATIONAL
SPECTRA
STRUCTURAL
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Structural, electronic, topological and vibrational propertiesof Eucalyptol have been theoretically studied in the gas phaseand in acetone, chloroform, ethanol, and water solutions byusing the hybrid B3LYP/6-31G* level of theory. Theproperties were evaluated in function of the solvent´spermittivities. A higher dipole moment and lower volumevalues were observed for eucalyptol in water due probably tothe higher permittivity. Also, higher corrected solvationenergy is predicted for eucalyptol in water (-22.51 kJ/mol) inagreement with the higher volume contraction observed inthis medium (-0.4 Å3). Atomic charges reveal the mostnegative values on the O atoms and the most positive valueson the C3 and C4 atoms. MEP surfaces of eucalyptol in allmedia evidence clear nucleophilic sites on the O atoms. NBO analyses show two E→* and ELP→* transitions while theAIM studies reveal two new H---H interactions which supportvisibly the stabilities of eucalyptol in all studied media. Thegap values show a decreasing in the reactivity of eucalyptol ingas phase and mainly in chloroform and acetone solutionswhile in aqueous solution eucalyptol is slightly most reactive.Besides, the higher nucleophilic indexes of eucalyptol in allsolvents support the characteristic nucleophilic of eucalyptol,as compared with scopolamine and tropane alkaloids. Theharmonic force fields and their complete vibrationalassignments of 81 normal vibration modes were performed.The predicted IR, ATR, Raman, 1H- and 13C-NMR and UVvisiblespectra show reasonable concordance with thecorresponding experimental ones.
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
description Structural, electronic, topological and vibrational propertiesof Eucalyptol have been theoretically studied in the gas phaseand in acetone, chloroform, ethanol, and water solutions byusing the hybrid B3LYP/6-31G* level of theory. Theproperties were evaluated in function of the solvent´spermittivities. A higher dipole moment and lower volumevalues were observed for eucalyptol in water due probably tothe higher permittivity. Also, higher corrected solvationenergy is predicted for eucalyptol in water (-22.51 kJ/mol) inagreement with the higher volume contraction observed inthis medium (-0.4 Å3). Atomic charges reveal the mostnegative values on the O atoms and the most positive valueson the C3 and C4 atoms. MEP surfaces of eucalyptol in allmedia evidence clear nucleophilic sites on the O atoms. NBO analyses show two E→* and ELP→* transitions while theAIM studies reveal two new H---H interactions which supportvisibly the stabilities of eucalyptol in all studied media. Thegap values show a decreasing in the reactivity of eucalyptol ingas phase and mainly in chloroform and acetone solutionswhile in aqueous solution eucalyptol is slightly most reactive.Besides, the higher nucleophilic indexes of eucalyptol in allsolvents support the characteristic nucleophilic of eucalyptol,as compared with scopolamine and tropane alkaloids. Theharmonic force fields and their complete vibrationalassignments of 81 normal vibration modes were performed.The predicted IR, ATR, Raman, 1H- and 13C-NMR and UVvisiblespectra show reasonable concordance with thecorresponding experimental ones.
publishDate 2019
dc.date.none.fl_str_mv 2019-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/119324
Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia; Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol; IJSRM; International Journal of Science and Research Methodology; 12; 3; 5-2019; 1-32
2454-2008
CONICET Digital
CONICET
url http://hdl.handle.net/11336/119324
identifier_str_mv Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia; Effect of Media on the Properties of Monoterpene Cyclic Eucalyptol; IJSRM; International Journal of Science and Research Methodology; 12; 3; 5-2019; 1-32
2454-2008
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://ijsrm.humanjournals.com/wp-content/uploads/2019/06/8.Maximiliano-A.-Iramain-Jos%C3%A9-Ruiz-Hidalgo-Silvia-Antonia-Brand%C3%A1n.pdf
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
dc.publisher.none.fl_str_mv IJSRM
publisher.none.fl_str_mv IJSRM
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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score 13.13397

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