Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives

Autores
Cayón, Vanina Mabel; Torrico Vallejos, Sonia; Della Védova, Carlos Omar; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Erben, Mauricio Federico
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
O-methyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)C(S)OCH3 (I), and O-ethyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)(S)OCH2CH3 (II), were prepared by the addition reaction between CH3CH2OC(O)NCS and the corresponding alcohols. Their structural and conformational properties were studied using lowtemperature single crystal X-ray diffraction and vibrational spectroscopy assisted by quantum chemical calculations. Compound I crystallizes in the monoclinic space group P21/n with lattice parameters a = 4.2450(1), b = 18.4992(5), c = 9.8759(3) Å, β = 95.887(3)° and 4 molecules per unit cell (Z=4), and II in the triclinic space group P1 with parameters a = 4.1771(8), b = 9.235(2), c = 11.804(2) Å and values angles α = 98.17(1),β = 98.62(1), γ = 102.29(2)°, and Z = 2. In the crystal, the conformation around the thiocarbamate group-N(H)C(S)O- is characterized by a synperiplanar orientation of the C=S double with respect to the N-H single bond, while the methoxycarbonyl C=O double bond is in antiperiplanar orientation with respect to the N-H bond. Both species form dimersl linked by NH???S=C hydrogen bond, the N???S non-bonding distance being 3.352(2) Å in compound I. Furthermore, ethoxycarbonylimidothiocarbonatespecies were obtained by the addition of methyl and n-butyl groups to the C=S double bond of I and II. Thus, species with formula CH3CH2OC(O)N=C(SCH3)OCH3 (III), CH3CH2OC(O)N=C(SCH3)OCH2CH3 (IV), as well as the novel compounds CH3CH2OC(O)N=C(SC4H9)OCH3 (V) and CH3CH2OC(O)N=C(SC4H9)OCH2CH3 (VI), were alsoprepared and fully characterized by spectroscopic methods.
Fil: Cayón, Vanina Mabel. 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: Torrico Vallejos, Sonia. 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: 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
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Erben, Mauricio Federico. 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
O-ALKYL-N-ETHOXYCARBONYLTHIOCARBAMATE
IMIDOTHIOCARBONATE
COFORMATION
STRUCTURE
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:11336/87548
Acceder
id CONICETDig_7eeec16f36a55aa8a44c0fe879af45c9
oai_identifier_str oai:ri.conicet.gov.ar:11336/87548
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivativesCayón, Vanina MabelTorrico Vallejos, SoniaDella Védova, Carlos OmarPiro, Oscar EnriqueEcheverría, Gustavo AlbertoErben, Mauricio FedericoO-ALKYL-N-ETHOXYCARBONYLTHIOCARBAMATEIMIDOTHIOCARBONATECOFORMATIONSTRUCTUREhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1O-methyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)C(S)OCH3 (I), and O-ethyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)(S)OCH2CH3 (II), were prepared by the addition reaction between CH3CH2OC(O)NCS and the corresponding alcohols. Their structural and conformational properties were studied using lowtemperature single crystal X-ray diffraction and vibrational spectroscopy assisted by quantum chemical calculations. Compound I crystallizes in the monoclinic space group P21/n with lattice parameters a = 4.2450(1), b = 18.4992(5), c = 9.8759(3) Å, β = 95.887(3)° and 4 molecules per unit cell (Z=4), and II in the triclinic space group P1 with parameters a = 4.1771(8), b = 9.235(2), c = 11.804(2) Å and values angles α = 98.17(1),β = 98.62(1), γ = 102.29(2)°, and Z = 2. In the crystal, the conformation around the thiocarbamate group-N(H)C(S)O- is characterized by a synperiplanar orientation of the C=S double with respect to the N-H single bond, while the methoxycarbonyl C=O double bond is in antiperiplanar orientation with respect to the N-H bond. Both species form dimersl linked by NH???S=C hydrogen bond, the N???S non-bonding distance being 3.352(2) Å in compound I. Furthermore, ethoxycarbonylimidothiocarbonatespecies were obtained by the addition of methyl and n-butyl groups to the C=S double bond of I and II. Thus, species with formula CH3CH2OC(O)N=C(SCH3)OCH3 (III), CH3CH2OC(O)N=C(SCH3)OCH2CH3 (IV), as well as the novel compounds CH3CH2OC(O)N=C(SC4H9)OCH3 (V) and CH3CH2OC(O)N=C(SC4H9)OCH2CH3 (VI), were alsoprepared and fully characterized by spectroscopic methods.Fil: Cayón, Vanina Mabel. 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: Torrico Vallejos, Sonia. 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: 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"; ArgentinaFil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: Erben, Mauricio Federico. 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"; ArgentinaResearch Trends2018-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/87548Cayón, Vanina Mabel; Torrico Vallejos, Sonia; Della Védova, Carlos Omar; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; et al.; Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives; Research Trends; Trends in Organic Chemistry; 19; 11-2018; 43-730972-4362CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.researchtrends.net/tia/abstract.asp?in=0&vn=19&tid=14&aid=6287&pub=2018&type=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 Técnicas2025-09-10T12:59:49Zoai:ri.conicet.gov.ar:11336/87548instacron: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:34982025-09-10 12:59:50.047CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
title Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
spellingShingle Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
Cayón, Vanina Mabel
O-ALKYL-N-ETHOXYCARBONYLTHIOCARBAMATE
IMIDOTHIOCARBONATE
COFORMATION
STRUCTURE
title_short Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
title_full Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
title_fullStr Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
title_full_unstemmed Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
title_sort Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives
dc.creator.none.fl_str_mv Cayón, Vanina Mabel
Torrico Vallejos, Sonia
Della Védova, Carlos Omar
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Erben, Mauricio Federico
author Cayón, Vanina Mabel
author_facet Cayón, Vanina Mabel
Torrico Vallejos, Sonia
Della Védova, Carlos Omar
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Erben, Mauricio Federico
author_role author
author2 Torrico Vallejos, Sonia
Della Védova, Carlos Omar
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Erben, Mauricio Federico
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv O-ALKYL-N-ETHOXYCARBONYLTHIOCARBAMATE
IMIDOTHIOCARBONATE
COFORMATION
STRUCTURE
topic O-ALKYL-N-ETHOXYCARBONYLTHIOCARBAMATE
IMIDOTHIOCARBONATE
COFORMATION
STRUCTURE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv O-methyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)C(S)OCH3 (I), and O-ethyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)(S)OCH2CH3 (II), were prepared by the addition reaction between CH3CH2OC(O)NCS and the corresponding alcohols. Their structural and conformational properties were studied using lowtemperature single crystal X-ray diffraction and vibrational spectroscopy assisted by quantum chemical calculations. Compound I crystallizes in the monoclinic space group P21/n with lattice parameters a = 4.2450(1), b = 18.4992(5), c = 9.8759(3) Å, β = 95.887(3)° and 4 molecules per unit cell (Z=4), and II in the triclinic space group P1 with parameters a = 4.1771(8), b = 9.235(2), c = 11.804(2) Å and values angles α = 98.17(1),β = 98.62(1), γ = 102.29(2)°, and Z = 2. In the crystal, the conformation around the thiocarbamate group-N(H)C(S)O- is characterized by a synperiplanar orientation of the C=S double with respect to the N-H single bond, while the methoxycarbonyl C=O double bond is in antiperiplanar orientation with respect to the N-H bond. Both species form dimersl linked by NH???S=C hydrogen bond, the N???S non-bonding distance being 3.352(2) Å in compound I. Furthermore, ethoxycarbonylimidothiocarbonatespecies were obtained by the addition of methyl and n-butyl groups to the C=S double bond of I and II. Thus, species with formula CH3CH2OC(O)N=C(SCH3)OCH3 (III), CH3CH2OC(O)N=C(SCH3)OCH2CH3 (IV), as well as the novel compounds CH3CH2OC(O)N=C(SC4H9)OCH3 (V) and CH3CH2OC(O)N=C(SC4H9)OCH2CH3 (VI), were alsoprepared and fully characterized by spectroscopic methods.
Fil: Cayón, Vanina Mabel. 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: Torrico Vallejos, Sonia. 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: 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
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Erben, Mauricio Federico. 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 O-methyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)C(S)OCH3 (I), and O-ethyl-N-ethoxycarbonylthiocarbamate, CH3CH2OC(O)N(H)(S)OCH2CH3 (II), were prepared by the addition reaction between CH3CH2OC(O)NCS and the corresponding alcohols. Their structural and conformational properties were studied using lowtemperature single crystal X-ray diffraction and vibrational spectroscopy assisted by quantum chemical calculations. Compound I crystallizes in the monoclinic space group P21/n with lattice parameters a = 4.2450(1), b = 18.4992(5), c = 9.8759(3) Å, β = 95.887(3)° and 4 molecules per unit cell (Z=4), and II in the triclinic space group P1 with parameters a = 4.1771(8), b = 9.235(2), c = 11.804(2) Å and values angles α = 98.17(1),β = 98.62(1), γ = 102.29(2)°, and Z = 2. In the crystal, the conformation around the thiocarbamate group-N(H)C(S)O- is characterized by a synperiplanar orientation of the C=S double with respect to the N-H single bond, while the methoxycarbonyl C=O double bond is in antiperiplanar orientation with respect to the N-H bond. Both species form dimersl linked by NH???S=C hydrogen bond, the N???S non-bonding distance being 3.352(2) Å in compound I. Furthermore, ethoxycarbonylimidothiocarbonatespecies were obtained by the addition of methyl and n-butyl groups to the C=S double bond of I and II. Thus, species with formula CH3CH2OC(O)N=C(SCH3)OCH3 (III), CH3CH2OC(O)N=C(SCH3)OCH2CH3 (IV), as well as the novel compounds CH3CH2OC(O)N=C(SC4H9)OCH3 (V) and CH3CH2OC(O)N=C(SC4H9)OCH2CH3 (VI), were alsoprepared and fully characterized by spectroscopic methods.
publishDate 2018
dc.date.none.fl_str_mv 2018-11
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/11336/87548
Cayón, Vanina Mabel; Torrico Vallejos, Sonia; Della Védova, Carlos Omar; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; et al.; Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives; Research Trends; Trends in Organic Chemistry; 19; 11-2018; 43-73
0972-4362
CONICET Digital
CONICET
url http://hdl.handle.net/11336/87548
identifier_str_mv Cayón, Vanina Mabel; Torrico Vallejos, Sonia; Della Védova, Carlos Omar; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; et al.; Structure of O-alkyl-N-ethoxycarbonyl thiocarbamate and imidothiocarbonate derivatives; Research Trends; Trends in Organic Chemistry; 19; 11-2018; 43-73
0972-4362
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://www.researchtrends.net/tia/abstract.asp?in=0&vn=19&tid=14&aid=6287&pub=2018&type=
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 Research Trends
publisher.none.fl_str_mv Research Trends
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 12.48226

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