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dc.contributor.author
Lobayan, Rosana M.
dc.contributor.author
Pérez Schmit, María C.
dc.contributor.author
Jubert, Alicia Haydee
dc.contributor.author
Vitale, Arturo Alberto
dc.date.available
2021-07-07T12:36:31Z
dc.date.issued
2012-11
dc.identifier.citation
Lobayan, Rosana M.; Pérez Schmit, María C.; Jubert, Alicia Haydee; Vitale, Arturo Alberto; Aqueous solvent effects on the conformational space of tryptamine: Structural and electronic analysis; Springer; Journal of Molecular Modeling; 19; 3; 11-2012; 1109-1123
dc.identifier.issn
1610-2940
dc.identifier.uri
http://hdl.handle.net/11336/135624
dc.description.abstract
The TRA (3-[2-aminoethyl]indole) is an important neurotransmitter with a close structural and chemical similarity to the neurotransmitter serotonin (5-hydroxytryptamine), and to melatonin (5-methoxy-N-acetyltryptamine), which plays a key role in daily human behavior. Moreover, TRA, and other indolic compounds are very efficient antioxidants. In this work the conformational space of TRA was scanned in aqueous solution, simulating the solvent by the polarizable continuum model. Geometry optimizations were performed at B3LYP/6-31+G** level. Electronic distributions were analyzed at a better calculation level, thus improving the basis set (6-311++G**). A topological study based on Bader’s theory (atoms in molecules) and natural bond orbital (NBO) framework was performed. Structural changes found in solution were related with charge delocalization mechanisms, which explained the changes in the conformational relative population in aqueous phase. Solvent effects on molecular electrostatic potential (MEPs) were also quantified and rationalized through charge delocalization mechanisms, thus connecting changes in MEPs with changes in structure, bond polarization, orbital bonding populations, natural charges, and bond topological properties. Moreover, polarizabilities and dipolar moments were calculated. All conformers were taken into account. Our results are the first prediction of TRA polarizabilities. The results reported contribute to the understanding of the structure, stability and reactivity of TRA and other indole derivatives.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Springer
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
(3-[2-AMINOETHYL]INDOLE)
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ANTIOXIDANTS
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AQUEOUS SOLVENT EFFECT
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ATOMS IN MOLECULES
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DENSITY FUNCTIONAL THEORY
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MOLECULAR DIPOLE MOMENT
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MOLECULAR POLARIZABILITY
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NATURAL BOND PRBITAL ANALYSIS
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PCM MODEL
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TRA
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TRYPTAMINE
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Química Orgánica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Aqueous solvent effects on the conformational space of tryptamine: Structural and electronic analysis
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-04-01T18:04:15Z
dc.journal.volume
19
dc.journal.number
3
dc.journal.pagination
1109-1123
dc.journal.pais
Alemania
dc.journal.ciudad
Berlin
dc.description.fil
Fil: Lobayan, Rosana M.. Universidad de la Cuenca del Plata; Argentina. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura; Argentina
dc.description.fil
Fil: Pérez Schmit, María C.. Universidad de la Cuenca del Plata; Argentina
dc.description.fil
Fil: Jubert, Alicia Haydee. 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
dc.description.fil
Fil: Vitale, Arturo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Bioquímica y Medicina Molecular. Universidad de Buenos Aires. Facultad Medicina. Instituto de Bioquímica y Medicina Molecular; Argentina
dc.journal.title
Journal of Molecular Modeling
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00894-012-1650-6
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1007/s00894-012-1650-6
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