Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3

Autores
Tuttolomondo, María Eugenia; Navarro, A.; Peña, T.; Varetti, Eduardo Lelio; Ben Altabef, Aida
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Ethyl methanesulfonate, CH3SO2OCH2CH 3, is well-known as an alkylating agent in mutagenic and carcinogenic processes. Its electronic structure and that of the methanesulfonate anion (CH3SO3-) were determined using optimization methods based on density functional theory and Moller-Plesset second-order perturbation theory. For CH3SO2OCH2CH 3, two conformations with symmetries Cs and C1 are obtained, the former being more stable than the latter. Natural bond orbital (NBO) calculations show the Cs conformation provides a more favorable geometry of the lone pairs of the oxygen atom linking the ethyl group. The NBO technique also reveals the characteristics of the methanesulfonate anion as a leaving group due to the rearrangement of the excess electronic charge after alkylation. Furthermore, the infrared spectra of CH 3SC2OCH2CH3 are reported for the liquid and solid states as well as the Raman spectrum of the liquid. Comparison to experiment of the conformationally averaged IR spectrum of Cs and C1 provides evidence of the predicted conformations in the solid IR spectrum. These experimental data along with the calculated theoretical force constants are used to define a scaled quantum mechanical force field for the target molecule, which allowed the measured frequencies to be reproduced with a final root-mean-square deviation of 9 cm-1 and, thus, a reliable assignment of the vibrational spectrum. © 2005 American Chemical Society.
Fil: Tuttolomondo, María Eugenia. Universidad Nacional de Tucumán; Argentina
Fil: Navarro, A.. Universidad de Jaén; España
Fil: Peña, T.. Universidad de Jaén; España
Fil: Varetti, Eduardo Lelio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de La Plata; Argentina
Fil: Ben Altabef, Aida. 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 Nacional de Tucumán; Argentina
Materia
Vibrational analysis
Theoretical structure
Infrared and Raman spectroscopy
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:11336/99475
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/99475
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3Tuttolomondo, María EugeniaNavarro, A.Peña, T.Varetti, Eduardo LelioBen Altabef, AidaVibrational analysisTheoretical structureInfrared and Raman spectroscopyhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Ethyl methanesulfonate, CH3SO2OCH2CH 3, is well-known as an alkylating agent in mutagenic and carcinogenic processes. Its electronic structure and that of the methanesulfonate anion (CH3SO3-) were determined using optimization methods based on density functional theory and Moller-Plesset second-order perturbation theory. For CH3SO2OCH2CH 3, two conformations with symmetries Cs and C1 are obtained, the former being more stable than the latter. Natural bond orbital (NBO) calculations show the Cs conformation provides a more favorable geometry of the lone pairs of the oxygen atom linking the ethyl group. The NBO technique also reveals the characteristics of the methanesulfonate anion as a leaving group due to the rearrangement of the excess electronic charge after alkylation. Furthermore, the infrared spectra of CH 3SC2OCH2CH3 are reported for the liquid and solid states as well as the Raman spectrum of the liquid. Comparison to experiment of the conformationally averaged IR spectrum of Cs and C1 provides evidence of the predicted conformations in the solid IR spectrum. These experimental data along with the calculated theoretical force constants are used to define a scaled quantum mechanical force field for the target molecule, which allowed the measured frequencies to be reproduced with a final root-mean-square deviation of 9 cm-1 and, thus, a reliable assignment of the vibrational spectrum. © 2005 American Chemical Society.Fil: Tuttolomondo, María Eugenia. Universidad Nacional de Tucumán; ArgentinaFil: Navarro, A.. Universidad de Jaén; EspañaFil: Peña, T.. Universidad de Jaén; EspañaFil: Varetti, Eduardo Lelio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de La Plata; ArgentinaFil: Ben Altabef, Aida. 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 Nacional de Tucumán; ArgentinaAmerican Chemical Society2005-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/99475Tuttolomondo, María Eugenia; Navarro, A.; Peña, T.; Varetti, Eduardo Lelio; Ben Altabef, Aida; Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3; American Chemical Society; Journal of Physical Chemistry A; 109; 35; 12-2005; 7946-79561089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jp0509865info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp0509865#info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:54:23Zoai:ri.conicet.gov.ar:11336/99475instacron: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 09:54:24.028CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
title Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
spellingShingle Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
Tuttolomondo, María Eugenia
Vibrational analysis
Theoretical structure
Infrared and Raman spectroscopy
title_short Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
title_full Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
title_fullStr Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
title_full_unstemmed Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
title_sort Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3
dc.creator.none.fl_str_mv Tuttolomondo, María Eugenia
Navarro, A.
Peña, T.
Varetti, Eduardo Lelio
Ben Altabef, Aida
author Tuttolomondo, María Eugenia
author_facet Tuttolomondo, María Eugenia
Navarro, A.
Peña, T.
Varetti, Eduardo Lelio
Ben Altabef, Aida
author_role author
author2 Navarro, A.
Peña, T.
Varetti, Eduardo Lelio
Ben Altabef, Aida
author2_role author
author
author
author
dc.subject.none.fl_str_mv Vibrational analysis
Theoretical structure
Infrared and Raman spectroscopy
topic Vibrational analysis
Theoretical structure
Infrared and Raman spectroscopy
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Ethyl methanesulfonate, CH3SO2OCH2CH 3, is well-known as an alkylating agent in mutagenic and carcinogenic processes. Its electronic structure and that of the methanesulfonate anion (CH3SO3-) were determined using optimization methods based on density functional theory and Moller-Plesset second-order perturbation theory. For CH3SO2OCH2CH 3, two conformations with symmetries Cs and C1 are obtained, the former being more stable than the latter. Natural bond orbital (NBO) calculations show the Cs conformation provides a more favorable geometry of the lone pairs of the oxygen atom linking the ethyl group. The NBO technique also reveals the characteristics of the methanesulfonate anion as a leaving group due to the rearrangement of the excess electronic charge after alkylation. Furthermore, the infrared spectra of CH 3SC2OCH2CH3 are reported for the liquid and solid states as well as the Raman spectrum of the liquid. Comparison to experiment of the conformationally averaged IR spectrum of Cs and C1 provides evidence of the predicted conformations in the solid IR spectrum. These experimental data along with the calculated theoretical force constants are used to define a scaled quantum mechanical force field for the target molecule, which allowed the measured frequencies to be reproduced with a final root-mean-square deviation of 9 cm-1 and, thus, a reliable assignment of the vibrational spectrum. © 2005 American Chemical Society.
Fil: Tuttolomondo, María Eugenia. Universidad Nacional de Tucumán; Argentina
Fil: Navarro, A.. Universidad de Jaén; España
Fil: Peña, T.. Universidad de Jaén; España
Fil: Varetti, Eduardo Lelio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de La Plata; Argentina
Fil: Ben Altabef, Aida. 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 Nacional de Tucumán; Argentina
description Ethyl methanesulfonate, CH3SO2OCH2CH 3, is well-known as an alkylating agent in mutagenic and carcinogenic processes. Its electronic structure and that of the methanesulfonate anion (CH3SO3-) were determined using optimization methods based on density functional theory and Moller-Plesset second-order perturbation theory. For CH3SO2OCH2CH 3, two conformations with symmetries Cs and C1 are obtained, the former being more stable than the latter. Natural bond orbital (NBO) calculations show the Cs conformation provides a more favorable geometry of the lone pairs of the oxygen atom linking the ethyl group. The NBO technique also reveals the characteristics of the methanesulfonate anion as a leaving group due to the rearrangement of the excess electronic charge after alkylation. Furthermore, the infrared spectra of CH 3SC2OCH2CH3 are reported for the liquid and solid states as well as the Raman spectrum of the liquid. Comparison to experiment of the conformationally averaged IR spectrum of Cs and C1 provides evidence of the predicted conformations in the solid IR spectrum. These experimental data along with the calculated theoretical force constants are used to define a scaled quantum mechanical force field for the target molecule, which allowed the measured frequencies to be reproduced with a final root-mean-square deviation of 9 cm-1 and, thus, a reliable assignment of the vibrational spectrum. © 2005 American Chemical Society.
publishDate 2005
dc.date.none.fl_str_mv 2005-12
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/11336/99475
Tuttolomondo, María Eugenia; Navarro, A.; Peña, T.; Varetti, Eduardo Lelio; Ben Altabef, Aida; Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3; American Chemical Society; Journal of Physical Chemistry A; 109; 35; 12-2005; 7946-7956
1089-5639
CONICET Digital
CONICET
url http://hdl.handle.net/11336/99475
identifier_str_mv Tuttolomondo, María Eugenia; Navarro, A.; Peña, T.; Varetti, Eduardo Lelio; Ben Altabef, Aida; Theoretical structure and vibrational analysis of Ethyl methanesulfonate, CH3so2OCH2CH3; American Chemical Society; Journal of Physical Chemistry A; 109; 35; 12-2005; 7946-7956
1089-5639
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jp0509865
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp0509865#
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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