Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3

Autores
Gómez Castaño, Jovanny Arles; Romano, Rosana Mariel; Salamanca, Ana R.; Amésquita, Germán; Beckers, Helmut; Willner, Helge; Della Védova, Carlos Omar
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
By oxidation of selenoacetic acid, CH3C(O)SeH, we have prepared the hitherto unknown diacetyl diselenide, [CH3C(O)Se]2. Its vibrational properties were studied experimentally, both in neat liquid (Fourier transform infrared spectroscopy and Raman) with the molecule isolated in argon matrix at low temperatures and theoretically using MP2 and B3LYP methods in combination with 6-31+G(d), 6-311++G(3df,3dp) or aug-cc-pvDZ basis sets. Analysis of Ar matrix spectra reveals a conformational equilibrium in gas phase at room temperature, which was interpreted by considering only two of the three stable rotamers predicted by our three-dimensional potential energy surface scans. Energetic properties of three minima found theoretically were further studied in terms of donor?acceptor interactions by using natural bond orbital calculations at the same levels of theory. From this, it was possible to rationalize the conformational stability order and molecular structures by means of vicinal hyperconjugative delocalizations involving lone pairs on selenium or oxygen atoms and C=O, C?C or Se?C antibonding orbitals. The photochemistry of the compound in the argon matrix in the range between 200 and 800 nm was also investigated, revealing only one photochemical path to produce ketene, H2C=C=O, methylselane, CH3SeH, and carbonyl selenide, OCSe. Copyright © 2016 John Wiley & Sons, Ltd.
Fil: Gómez Castaño, Jovanny Arles. 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 Pedagógica y Tecnológica de Colombia; Colombia
Fil: Romano, Rosana Mariel. 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
Fil: Salamanca, Ana R.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Amésquita, Germán. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Beckers, Helmut. Bergische Universität Wuppertal; Alemania
Fil: Willner, Helge. Bergische Universität Wuppertal; Alemania
Fil: Della Védova, Carlos Omar. 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
Materia
Diselenide
Hyperconjugation
Matrix Photochemistry
Nbo
Photodecomposition
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:11336/48429
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/48429
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3Gómez Castaño, Jovanny ArlesRomano, Rosana MarielSalamanca, Ana R.Amésquita, GermánBeckers, HelmutWillner, HelgeDella Védova, Carlos OmarDiselenideHyperconjugationMatrix PhotochemistryNboPhotodecompositionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1By oxidation of selenoacetic acid, CH3C(O)SeH, we have prepared the hitherto unknown diacetyl diselenide, [CH3C(O)Se]2. Its vibrational properties were studied experimentally, both in neat liquid (Fourier transform infrared spectroscopy and Raman) with the molecule isolated in argon matrix at low temperatures and theoretically using MP2 and B3LYP methods in combination with 6-31+G(d), 6-311++G(3df,3dp) or aug-cc-pvDZ basis sets. Analysis of Ar matrix spectra reveals a conformational equilibrium in gas phase at room temperature, which was interpreted by considering only two of the three stable rotamers predicted by our three-dimensional potential energy surface scans. Energetic properties of three minima found theoretically were further studied in terms of donor?acceptor interactions by using natural bond orbital calculations at the same levels of theory. From this, it was possible to rationalize the conformational stability order and molecular structures by means of vicinal hyperconjugative delocalizations involving lone pairs on selenium or oxygen atoms and C=O, C?C or Se?C antibonding orbitals. The photochemistry of the compound in the argon matrix in the range between 200 and 800 nm was also investigated, revealing only one photochemical path to produce ketene, H2C=C=O, methylselane, CH3SeH, and carbonyl selenide, OCSe. Copyright © 2016 John Wiley & Sons, Ltd.Fil: Gómez Castaño, Jovanny Arles. 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 Pedagógica y Tecnológica de Colombia; ColombiaFil: Romano, Rosana Mariel. 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"; ArgentinaFil: Salamanca, Ana R.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Amésquita, Germán. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Beckers, Helmut. Bergische Universität Wuppertal; AlemaniaFil: Willner, Helge. Bergische Universität Wuppertal; AlemaniaFil: Della Védova, Carlos Omar. 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"; ArgentinaJohn Wiley & Sons Ltd2016-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48429Gómez Castaño, Jovanny Arles; Romano, Rosana Mariel; Salamanca, Ana R.; Amésquita, Germán; Beckers, Helmut; et al.; Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 29; 11; 11-2016; 636-6440894-3230CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3587info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.3587info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:45:25Zoai:ri.conicet.gov.ar:11336/48429instacron: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:34982025-09-29 10:45:25.301CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
title Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
spellingShingle Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
Gómez Castaño, Jovanny Arles
Diselenide
Hyperconjugation
Matrix Photochemistry
Nbo
Photodecomposition
title_short Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
title_full Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
title_fullStr Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
title_full_unstemmed Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
title_sort Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3
dc.creator.none.fl_str_mv Gómez Castaño, Jovanny Arles
Romano, Rosana Mariel
Salamanca, Ana R.
Amésquita, Germán
Beckers, Helmut
Willner, Helge
Della Védova, Carlos Omar
author Gómez Castaño, Jovanny Arles
author_facet Gómez Castaño, Jovanny Arles
Romano, Rosana Mariel
Salamanca, Ana R.
Amésquita, Germán
Beckers, Helmut
Willner, Helge
Della Védova, Carlos Omar
author_role author
author2 Romano, Rosana Mariel
Salamanca, Ana R.
Amésquita, Germán
Beckers, Helmut
Willner, Helge
Della Védova, Carlos Omar
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Diselenide
Hyperconjugation
Matrix Photochemistry
Nbo
Photodecomposition
topic Diselenide
Hyperconjugation
Matrix Photochemistry
Nbo
Photodecomposition
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv By oxidation of selenoacetic acid, CH3C(O)SeH, we have prepared the hitherto unknown diacetyl diselenide, [CH3C(O)Se]2. Its vibrational properties were studied experimentally, both in neat liquid (Fourier transform infrared spectroscopy and Raman) with the molecule isolated in argon matrix at low temperatures and theoretically using MP2 and B3LYP methods in combination with 6-31+G(d), 6-311++G(3df,3dp) or aug-cc-pvDZ basis sets. Analysis of Ar matrix spectra reveals a conformational equilibrium in gas phase at room temperature, which was interpreted by considering only two of the three stable rotamers predicted by our three-dimensional potential energy surface scans. Energetic properties of three minima found theoretically were further studied in terms of donor?acceptor interactions by using natural bond orbital calculations at the same levels of theory. From this, it was possible to rationalize the conformational stability order and molecular structures by means of vicinal hyperconjugative delocalizations involving lone pairs on selenium or oxygen atoms and C=O, C?C or Se?C antibonding orbitals. The photochemistry of the compound in the argon matrix in the range between 200 and 800 nm was also investigated, revealing only one photochemical path to produce ketene, H2C=C=O, methylselane, CH3SeH, and carbonyl selenide, OCSe. Copyright © 2016 John Wiley & Sons, Ltd.
Fil: Gómez Castaño, Jovanny Arles. 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 Pedagógica y Tecnológica de Colombia; Colombia
Fil: Romano, Rosana Mariel. 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
Fil: Salamanca, Ana R.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Amésquita, Germán. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Beckers, Helmut. Bergische Universität Wuppertal; Alemania
Fil: Willner, Helge. Bergische Universität Wuppertal; Alemania
Fil: Della Védova, Carlos Omar. 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
description By oxidation of selenoacetic acid, CH3C(O)SeH, we have prepared the hitherto unknown diacetyl diselenide, [CH3C(O)Se]2. Its vibrational properties were studied experimentally, both in neat liquid (Fourier transform infrared spectroscopy and Raman) with the molecule isolated in argon matrix at low temperatures and theoretically using MP2 and B3LYP methods in combination with 6-31+G(d), 6-311++G(3df,3dp) or aug-cc-pvDZ basis sets. Analysis of Ar matrix spectra reveals a conformational equilibrium in gas phase at room temperature, which was interpreted by considering only two of the three stable rotamers predicted by our three-dimensional potential energy surface scans. Energetic properties of three minima found theoretically were further studied in terms of donor?acceptor interactions by using natural bond orbital calculations at the same levels of theory. From this, it was possible to rationalize the conformational stability order and molecular structures by means of vicinal hyperconjugative delocalizations involving lone pairs on selenium or oxygen atoms and C=O, C?C or Se?C antibonding orbitals. The photochemistry of the compound in the argon matrix in the range between 200 and 800 nm was also investigated, revealing only one photochemical path to produce ketene, H2C=C=O, methylselane, CH3SeH, and carbonyl selenide, OCSe. Copyright © 2016 John Wiley & Sons, Ltd.
publishDate 2016
dc.date.none.fl_str_mv 2016-11
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/11336/48429
Gómez Castaño, Jovanny Arles; Romano, Rosana Mariel; Salamanca, Ana R.; Amésquita, Germán; Beckers, Helmut; et al.; Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 29; 11; 11-2016; 636-644
0894-3230
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48429
identifier_str_mv Gómez Castaño, Jovanny Arles; Romano, Rosana Mariel; Salamanca, Ana R.; Amésquita, Germán; Beckers, Helmut; et al.; Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH 3 C(O)Se 2 C(O)CH 3; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 29; 11; 11-2016; 636-644
0894-3230
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3587
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.3587
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 John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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 13.070432

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