Proton Affinity and Protonation Sites in p-Nitroaniline
ABSTRACT: We present a study of the effect that substituents with competitive inductive properties have on the reactivity of the aromatic ring. As specific case, we studied the gas phase protonation of paranitroaniline (PNA) using Density Functional Theory methods (DFT) and Moller Plesset second ord...
- Autores:
-
Jaramillo Paniagua, Cinthia
Moreno Ariza, Luis Fernando
Restrepo Cossio, Albeiro Alonso
- Tipo de recurso:
- Article of investigation
- Fecha de publicación:
- 2009
- Institución:
- Universidad de Antioquia
- Repositorio:
- Repositorio UdeA
- Idioma:
- eng
- OAI Identifier:
- oai:bibliotecadigital.udea.edu.co:10495/26691
- Acceso en línea:
- http://hdl.handle.net/10495/26691
https://revistas.unal.edu.co/index.php/rcolquim/article/view/10414
- Palabra clave:
- Protones
Protons
Reactividad (Química)
Reactivity Chemistry
Afinidad química
Chemical affinity
Reactivity in aromatic rings
Competitive inductive effects
p-Nitroanline
- Rights
- openAccess
- License
- http://creativecommons.org/licenses/by/2.5/co/
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| dc.title.spa.fl_str_mv |
Proton Affinity and Protonation Sites in p-Nitroaniline |
| dc.title.alternative.spa.fl_str_mv |
Afinidad protónica e lugares de protonación em p-nitroaniline |
| title |
Proton Affinity and Protonation Sites in p-Nitroaniline |
| spellingShingle |
Proton Affinity and Protonation Sites in p-Nitroaniline Protones Protons Reactividad (Química) Reactivity Chemistry Afinidad química Chemical affinity Reactivity in aromatic rings Competitive inductive effects p-Nitroanline |
| title_short |
Proton Affinity and Protonation Sites in p-Nitroaniline |
| title_full |
Proton Affinity and Protonation Sites in p-Nitroaniline |
| title_fullStr |
Proton Affinity and Protonation Sites in p-Nitroaniline |
| title_full_unstemmed |
Proton Affinity and Protonation Sites in p-Nitroaniline |
| title_sort |
Proton Affinity and Protonation Sites in p-Nitroaniline |
| dc.creator.fl_str_mv |
Jaramillo Paniagua, Cinthia Moreno Ariza, Luis Fernando Restrepo Cossio, Albeiro Alonso |
| dc.contributor.author.none.fl_str_mv |
Jaramillo Paniagua, Cinthia Moreno Ariza, Luis Fernando Restrepo Cossio, Albeiro Alonso |
| dc.subject.lemb.none.fl_str_mv |
Protones Protons Reactividad (Química) Reactivity Chemistry Afinidad química Chemical affinity |
| topic |
Protones Protons Reactividad (Química) Reactivity Chemistry Afinidad química Chemical affinity Reactivity in aromatic rings Competitive inductive effects p-Nitroanline |
| dc.subject.proposal.spa.fl_str_mv |
Reactivity in aromatic rings Competitive inductive effects p-Nitroanline |
| description |
ABSTRACT: We present a study of the effect that substituents with competitive inductive properties have on the reactivity of the aromatic ring. As specific case, we studied the gas phase protonation of paranitroaniline (PNA) using Density Functional Theory methods (DFT) and Moller Plesset second order perturbation Theory (MP2). The joint effect of the substituents yields relative stabilities on the protoanted species that follow the trend nitro group > amino group > ortho carbon > para carbon > meta carbon > ipso carbon (positions relative to the amino group). |
| publishDate |
2009 |
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2009 |
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2022-03-17T15:27:34Z |
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2022-03-17T15:27:34Z |
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Artículo de investigación |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
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Jaramillo, Cinthia, & Moreno, Luis Fernando, & Restrepo, Albeiro (2009). Proton Affinity and Protonation Sites in p-Nitroaniline. Revista Colombiana de Química, 38(1),127-134.[fecha de Consulta 13 de Febrero de 2022]. ISSN: 0120-2804. Disponible en: https://revistas.unal.edu.co/index.php/rcolquim/article/view/10414 |
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0120-2804 |
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http://hdl.handle.net/10495/26691 |
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2357-3791 |
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https://revistas.unal.edu.co/index.php/rcolquim/article/view/10414 |
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Jaramillo, Cinthia, & Moreno, Luis Fernando, & Restrepo, Albeiro (2009). Proton Affinity and Protonation Sites in p-Nitroaniline. Revista Colombiana de Química, 38(1),127-134.[fecha de Consulta 13 de Febrero de 2022]. ISSN: 0120-2804. Disponible en: https://revistas.unal.edu.co/index.php/rcolquim/article/view/10414 0120-2804 2357-3791 |
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http://hdl.handle.net/10495/26691 https://revistas.unal.edu.co/index.php/rcolquim/article/view/10414 |
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eng |
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eng |
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Rev. Colomb. Quím. |
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info:eu-repo/semantics/openAccess |
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http://creativecommons.org/licenses/by/2.5/co/ |
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openAccess |
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Universidad Nacional de Colombia, Facultad de Ciencias, Departamento de Química |
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Grupo de Química-Física Teórica |
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Bogotá, Colombia |
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Universidad de Antioquia |
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Jaramillo Paniagua, CinthiaMoreno Ariza, Luis FernandoRestrepo Cossio, Albeiro Alonso2022-03-17T15:27:34Z2022-03-17T15:27:34Z2009Jaramillo, Cinthia, & Moreno, Luis Fernando, & Restrepo, Albeiro (2009). Proton Affinity and Protonation Sites in p-Nitroaniline. Revista Colombiana de Química, 38(1),127-134.[fecha de Consulta 13 de Febrero de 2022]. ISSN: 0120-2804. Disponible en: https://revistas.unal.edu.co/index.php/rcolquim/article/view/104140120-2804http://hdl.handle.net/10495/266912357-3791https://revistas.unal.edu.co/index.php/rcolquim/article/view/10414ABSTRACT: We present a study of the effect that substituents with competitive inductive properties have on the reactivity of the aromatic ring. As specific case, we studied the gas phase protonation of paranitroaniline (PNA) using Density Functional Theory methods (DFT) and Moller Plesset second order perturbation Theory (MP2). The joint effect of the substituents yields relative stabilities on the protoanted species that follow the trend nitro group > amino group > ortho carbon > para carbon > meta carbon > ipso carbon (positions relative to the amino group).RESUMEN: Se presenta un estudio del efecto de sustituyentes con propiedades inductivas competitivas sobre la reactividad en el anillo aromático. Como caso específico se estudió la protonación de la para nitro anilina (PNA) en fase gaseosa utilizando métodos de teoría de los funcionales de la densidad (DFT) y teoría de perturbaciones de segundo orden bajo el formalismo de Moller Plesset (MP2). El efecto conjunto de los sustituyentes conduce a estabilidades relativas para las especies protonadas de acuerdo con la siguiente escala: grupo nitro > grupo amino > carbono orto > carbono para > carbono meta > carbono ipso (posiciones relativas al grupo amino).COL00043999application/pdfengUniversidad Nacional de Colombia, Facultad de Ciencias, Departamento de QuímicaGrupo de Química-Física TeóricaBogotá, Colombiainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARTArtículo de investigaciónhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/2.5/co/http://purl.org/coar/access_right/c_abf2https://creativecommons.org/licenses/by/4.0/Proton Affinity and Protonation Sites in p-NitroanilineAfinidad protónica e lugares de protonación em p-nitroanilineProtonesProtonsReactividad (Química)Reactivity ChemistryAfinidad químicaChemical affinityReactivity in aromatic ringsCompetitive inductive effectsp-NitroanlineRev. Colomb. Quím.Revista Colombiana de Química127134381ORIGINALJaramilloCinthia_2009_ProtonAffinityProtonation.pdfJaramilloCinthia_2009_ProtonAffinityProtonation.pdfArtículo de investigaciónapplication/pdf260914http://bibliotecadigital.udea.edu.co/bitstream/10495/26691/4/JaramilloCinthia_2009_ProtonAffinityProtonation.pdfa034c32d51ba1940d1d97e01f00d0dcdMD54CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8927http://bibliotecadigital.udea.edu.co/bitstream/10495/26691/2/license_rdf1646d1f6b96dbbbc38035efc9239ac9cMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://bibliotecadigital.udea.edu.co/bitstream/10495/26691/3/license.txt8a4605be74aa9ea9d79846c1fba20a33MD5310495/26691oai:bibliotecadigital.udea.edu.co:10495/266912022-03-17 10:31:06.858Repositorio Institucional Universidad de Antioquiaandres.perez@udea.edu.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 |