Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and th...

Autores: Saeed, Aamer; Khurshid, Asma; Jasinski, Jerry P.; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; Erben, Mauricio Federico
Año de publicación: 2014
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: The synthesis of a novel 1-acyl-thiourea species (C14H17N2O2SCl), has been tailored in such a way that two distinct N–H...O=C intramolecular competing hydrogen bonds are feasible. The X-ray structure analysis as well as the vibrational (FT-IR and FT-Raman) data reveal that the S conformation is preferred, with the C=O and C=S bonds of the acyl-thiourea group pointing in opposite directions. The preference for the intramolecular N–H...O=C hydrogen bond within the –C(O)NHC(S)NH– core is confirmed. The Natural Bond Orbital and the Atom in Molecule approaches demonstrate that a strong hyperconjugative lpO → σ∗(N–H) remote interaction between the acyl and the thioamide N–H groups is responsible for the stabilization of the S conformation. Intermolecular interactions have been characterized in the periodic system electron density and the topological analysis reveals the presence of an extended intermolecular network in the crystal, including a Cl⋯N interaction playing a relevant role in crystal packing.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Khurshid, Asma. Quaid-I-Azam University; Pakistán
Fil: Jasinski, Jerry P.. Keene State College; Estados Unidos
Fil: Pozzi, Carlos Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. 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. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Materia: Crystal Structure
Hydrogen Bond
Nbo
Topological Analysis
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/23728

Acceder

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network_name_str	CONICET Digital (CONICET)
spelling	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methodsSaeed, AamerKhurshid, AsmaJasinski, Jerry P.Pozzi, Carlos GustavoFantoni, Adolfo CarlosErben, Mauricio FedericoCrystal StructureHydrogen BondNboTopological Analysishttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1The synthesis of a novel 1-acyl-thiourea species (C14H17N2O2SCl), has been tailored in such a way that two distinct N–H...O=C intramolecular competing hydrogen bonds are feasible. The X-ray structure analysis as well as the vibrational (FT-IR and FT-Raman) data reveal that the S conformation is preferred, with the C=O and C=S bonds of the acyl-thiourea group pointing in opposite directions. The preference for the intramolecular N–H...O=C hydrogen bond within the –C(O)NHC(S)NH– core is confirmed. The Natural Bond Orbital and the Atom in Molecule approaches demonstrate that a strong hyperconjugative lpO → σ∗(N–H) remote interaction between the acyl and the thioamide N–H groups is responsible for the stabilization of the S conformation. Intermolecular interactions have been characterized in the periodic system electron density and the topological analysis reveals the presence of an extended intermolecular network in the crystal, including a Cl⋯N interaction playing a relevant role in crystal packing.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Khurshid, Asma. Quaid-I-Azam University; PakistánFil: Jasinski, Jerry P.. Keene State College; Estados UnidosFil: Pozzi, Carlos Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. 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"; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; ArgentinaElsevier2014-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/23728Saeed, Aamer; Khurshid, Asma; Jasinski, Jerry P.; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; et al.; Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods; Elsevier; Chemical Physics; 431-432; 1-2014; 39-460301-0104CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0301010414000196info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chemphys.2014.01.009info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:48:54Zoai:ri.conicet.gov.ar:11336/23728instacron: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 09:48:55.171CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
title	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
spellingShingle	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods Saeed, Aamer Crystal Structure Hydrogen Bond Nbo Topological Analysis
title_short	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
title_full	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
title_fullStr	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
title_full_unstemmed	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
title_sort	Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
dc.creator.none.fl_str_mv	Saeed, Aamer Khurshid, Asma Jasinski, Jerry P. Pozzi, Carlos Gustavo Fantoni, Adolfo Carlos Erben, Mauricio Federico
author	Saeed, Aamer
author_facet	Saeed, Aamer Khurshid, Asma Jasinski, Jerry P. Pozzi, Carlos Gustavo Fantoni, Adolfo Carlos Erben, Mauricio Federico
author_role	author
author2	Khurshid, Asma Jasinski, Jerry P. Pozzi, Carlos Gustavo Fantoni, Adolfo Carlos Erben, Mauricio Federico
author2_role	author author author author author
dc.subject.none.fl_str_mv	Crystal Structure Hydrogen Bond Nbo Topological Analysis
topic	Crystal Structure Hydrogen Bond Nbo Topological Analysis
purl_subject.fl_str_mv	https://purl.org/becyt/ford/1.3 https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv	The synthesis of a novel 1-acyl-thiourea species (C14H17N2O2SCl), has been tailored in such a way that two distinct N–H...O=C intramolecular competing hydrogen bonds are feasible. The X-ray structure analysis as well as the vibrational (FT-IR and FT-Raman) data reveal that the S conformation is preferred, with the C=O and C=S bonds of the acyl-thiourea group pointing in opposite directions. The preference for the intramolecular N–H...O=C hydrogen bond within the –C(O)NHC(S)NH– core is confirmed. The Natural Bond Orbital and the Atom in Molecule approaches demonstrate that a strong hyperconjugative lpO → σ∗(N–H) remote interaction between the acyl and the thioamide N–H groups is responsible for the stabilization of the S conformation. Intermolecular interactions have been characterized in the periodic system electron density and the topological analysis reveals the presence of an extended intermolecular network in the crystal, including a Cl⋯N interaction playing a relevant role in crystal packing. Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán Fil: Khurshid, Asma. Quaid-I-Azam University; Pakistán Fil: Jasinski, Jerry P.. Keene State College; Estados Unidos Fil: Pozzi, Carlos Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina Fil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. 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. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
description	The synthesis of a novel 1-acyl-thiourea species (C14H17N2O2SCl), has been tailored in such a way that two distinct N–H...O=C intramolecular competing hydrogen bonds are feasible. The X-ray structure analysis as well as the vibrational (FT-IR and FT-Raman) data reveal that the S conformation is preferred, with the C=O and C=S bonds of the acyl-thiourea group pointing in opposite directions. The preference for the intramolecular N–H...O=C hydrogen bond within the –C(O)NHC(S)NH– core is confirmed. The Natural Bond Orbital and the Atom in Molecule approaches demonstrate that a strong hyperconjugative lpO → σ∗(N–H) remote interaction between the acyl and the thioamide N–H groups is responsible for the stabilization of the S conformation. Intermolecular interactions have been characterized in the periodic system electron density and the topological analysis reveals the presence of an extended intermolecular network in the crystal, including a Cl⋯N interaction playing a relevant role in crystal packing.
publishDate	2014
dc.date.none.fl_str_mv	2014-01
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/11336/23728 Saeed, Aamer; Khurshid, Asma; Jasinski, Jerry P.; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; et al.; Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods; Elsevier; Chemical Physics; 431-432; 1-2014; 39-46 0301-0104 CONICET Digital CONICET
url	http://hdl.handle.net/11336/23728
identifier_str_mv	Saeed, Aamer; Khurshid, Asma; Jasinski, Jerry P.; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; et al.; Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods; Elsevier; Chemical Physics; 431-432; 1-2014; 39-46 0301-0104 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.sciencedirect.com/science/article/pii/S0301010414000196 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chemphys.2014.01.009
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	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)
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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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Competing intramolecular N–H...O=C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and th...

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