Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study

Autores
Lobayan, Rosana M.; Pérez Schmit, María C.; Jubert, Alicia Haydeé; Vitale, Arturo Alberto
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Due to the free radical scavenger properties of Tryptamine (TRA), as well as of others indole derivatives, it is in our interest to explore deeply the stereoelectronic aspects that would be relevant in their stabilization and antioxidant activity. In this work the conformational space of TRA was scanned using molecular dynamics complemented with functional density calculations at B3LYP/6-31 + G** level. Twenty one conformers of lowest energy were obtained, their electronic distributions were analyzed at a higher calculation level, thus improving the basis set (B3LYP/6-311++G**). A topological study based on Bader’s theory (AIM: atoms in molecules) and natural bond orbital (NBO) framework was performed. The study was enriched by a deep analysis of maps of molecular electrostatic potential (MEP) through a coordinated NBO/AIM analysis. The conformational preferences were explained by hyperconjugative interactions, which were revealed by NBO data. Because radical scavenging by indolic compounds is strongly modulated by their functional residues our study was related to similar analysis done previously on Indole and 1H-indole-3-acetic acid (IAA). Therefore, the conformational space of TRA was studied from a new perspective focusing on a deep analysis of the geometric and electronic properties of TRA conformers. The changes of the electronic distribution introduced by the substituent and the conformational flexibility of the side chain were addressed. The results reported contribute to the understanding of the structure, stability and reactivity of TRA and others indole derivatives.
Centro de Química Inorgánica
Materia
Ciencias Exactas
Química
Antioxidants
Atoms in molecules theory
Density functional theory
Molecular electrostatic potential
Natural bond orbital analysis
Tryptamine
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/136127

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network_name_str SEDICI (UNLP)
spelling Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO studyLobayan, Rosana M.Pérez Schmit, María C.Jubert, Alicia HaydeéVitale, Arturo AlbertoCiencias ExactasQuímicaAntioxidantsAtoms in molecules theoryDensity functional theoryMolecular electrostatic potentialNatural bond orbital analysisTryptamineDue to the free radical scavenger properties of Tryptamine (TRA), as well as of others indole derivatives, it is in our interest to explore deeply the stereoelectronic aspects that would be relevant in their stabilization and antioxidant activity. In this work the conformational space of TRA was scanned using molecular dynamics complemented with functional density calculations at B3LYP/6-31 + G** level. Twenty one conformers of lowest energy were obtained, their electronic distributions were analyzed at a higher calculation level, thus improving the basis set (B3LYP/6-311++G**). A topological study based on Bader’s theory (AIM: atoms in molecules) and natural bond orbital (NBO) framework was performed. The study was enriched by a deep analysis of maps of molecular electrostatic potential (MEP) through a coordinated NBO/AIM analysis. The conformational preferences were explained by hyperconjugative interactions, which were revealed by NBO data. Because radical scavenging by indolic compounds is strongly modulated by their functional residues our study was related to similar analysis done previously on Indole and 1H-indole-3-acetic acid (IAA). Therefore, the conformational space of TRA was studied from a new perspective focusing on a deep analysis of the geometric and electronic properties of TRA conformers. The changes of the electronic distribution introduced by the substituent and the conformational flexibility of the side chain were addressed. The results reported contribute to the understanding of the structure, stability and reactivity of TRA and others indole derivatives.Centro de Química Inorgánica2012-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf2577-2588http://sedici.unlp.edu.ar/handle/10915/136127enginfo:eu-repo/semantics/altIdentifier/issn/0948-5023info:eu-repo/semantics/altIdentifier/issn/1610-2940info:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-011-1271-5info:eu-repo/semantics/altIdentifier/pmid/22072379info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:31:58Zoai:sedici.unlp.edu.ar:10915/136127Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:31:58.33SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
title Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
spellingShingle Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
Lobayan, Rosana M.
Ciencias Exactas
Química
Antioxidants
Atoms in molecules theory
Density functional theory
Molecular electrostatic potential
Natural bond orbital analysis
Tryptamine
title_short Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
title_full Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
title_fullStr Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
title_full_unstemmed Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
title_sort Conformational and stereoelectronic investigation of tryptamine : An AIM/NBO study
dc.creator.none.fl_str_mv Lobayan, Rosana M.
Pérez Schmit, María C.
Jubert, Alicia Haydeé
Vitale, Arturo Alberto
author Lobayan, Rosana M.
author_facet Lobayan, Rosana M.
Pérez Schmit, María C.
Jubert, Alicia Haydeé
Vitale, Arturo Alberto
author_role author
author2 Pérez Schmit, María C.
Jubert, Alicia Haydeé
Vitale, Arturo Alberto
author2_role author
author
author
dc.subject.none.fl_str_mv Ciencias Exactas
Química
Antioxidants
Atoms in molecules theory
Density functional theory
Molecular electrostatic potential
Natural bond orbital analysis
Tryptamine
topic Ciencias Exactas
Química
Antioxidants
Atoms in molecules theory
Density functional theory
Molecular electrostatic potential
Natural bond orbital analysis
Tryptamine
dc.description.none.fl_txt_mv Due to the free radical scavenger properties of Tryptamine (TRA), as well as of others indole derivatives, it is in our interest to explore deeply the stereoelectronic aspects that would be relevant in their stabilization and antioxidant activity. In this work the conformational space of TRA was scanned using molecular dynamics complemented with functional density calculations at B3LYP/6-31 + G** level. Twenty one conformers of lowest energy were obtained, their electronic distributions were analyzed at a higher calculation level, thus improving the basis set (B3LYP/6-311++G**). A topological study based on Bader’s theory (AIM: atoms in molecules) and natural bond orbital (NBO) framework was performed. The study was enriched by a deep analysis of maps of molecular electrostatic potential (MEP) through a coordinated NBO/AIM analysis. The conformational preferences were explained by hyperconjugative interactions, which were revealed by NBO data. Because radical scavenging by indolic compounds is strongly modulated by their functional residues our study was related to similar analysis done previously on Indole and 1H-indole-3-acetic acid (IAA). Therefore, the conformational space of TRA was studied from a new perspective focusing on a deep analysis of the geometric and electronic properties of TRA conformers. The changes of the electronic distribution introduced by the substituent and the conformational flexibility of the side chain were addressed. The results reported contribute to the understanding of the structure, stability and reactivity of TRA and others indole derivatives.
Centro de Química Inorgánica
description Due to the free radical scavenger properties of Tryptamine (TRA), as well as of others indole derivatives, it is in our interest to explore deeply the stereoelectronic aspects that would be relevant in their stabilization and antioxidant activity. In this work the conformational space of TRA was scanned using molecular dynamics complemented with functional density calculations at B3LYP/6-31 + G** level. Twenty one conformers of lowest energy were obtained, their electronic distributions were analyzed at a higher calculation level, thus improving the basis set (B3LYP/6-311++G**). A topological study based on Bader’s theory (AIM: atoms in molecules) and natural bond orbital (NBO) framework was performed. The study was enriched by a deep analysis of maps of molecular electrostatic potential (MEP) through a coordinated NBO/AIM analysis. The conformational preferences were explained by hyperconjugative interactions, which were revealed by NBO data. Because radical scavenging by indolic compounds is strongly modulated by their functional residues our study was related to similar analysis done previously on Indole and 1H-indole-3-acetic acid (IAA). Therefore, the conformational space of TRA was studied from a new perspective focusing on a deep analysis of the geometric and electronic properties of TRA conformers. The changes of the electronic distribution introduced by the substituent and the conformational flexibility of the side chain were addressed. The results reported contribute to the understanding of the structure, stability and reactivity of TRA and others indole derivatives.
publishDate 2012
dc.date.none.fl_str_mv 2012-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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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://sedici.unlp.edu.ar/handle/10915/136127
url http://sedici.unlp.edu.ar/handle/10915/136127
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/0948-5023
info:eu-repo/semantics/altIdentifier/issn/1610-2940
info:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-011-1271-5
info:eu-repo/semantics/altIdentifier/pmid/22072379
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
2577-2588
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repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
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