dc.creatorLobayan, Rosana M.
dc.creatorPérez Schmit, María C.
dc.creatorJubert, Alicia Haydee
dc.creatorVitale, Arturo Alberto
dc.date.accessioned2021-07-07T12:36:31Z
dc.date.accessioned2022-10-15T08:00:26Z
dc.date.available2021-07-07T12:36:31Z
dc.date.available2022-10-15T08:00:26Z
dc.date.created2021-07-07T12:36:31Z
dc.date.issued2012-11
dc.identifierLobayan, 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.identifier1610-2940
dc.identifierhttp://hdl.handle.net/11336/135624
dc.identifierCONICET Digital
dc.identifierCONICET
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/4363211
dc.description.abstractThe 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.languageeng
dc.publisherSpringer
dc.relationinfo:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00894-012-1650-6
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1007/s00894-012-1650-6
dc.rightshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject(3-[2-AMINOETHYL]INDOLE)
dc.subjectANTIOXIDANTS
dc.subjectAQUEOUS SOLVENT EFFECT
dc.subjectATOMS IN MOLECULES
dc.subjectDENSITY FUNCTIONAL THEORY
dc.subjectMOLECULAR DIPOLE MOMENT
dc.subjectMOLECULAR POLARIZABILITY
dc.subjectNATURAL BOND PRBITAL ANALYSIS
dc.subjectPCM MODEL
dc.subjectTRA
dc.subjectTRYPTAMINE
dc.titleAqueous solvent effects on the conformational space of tryptamine: Structural and electronic analysis
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:ar-repo/semantics/artículo
dc.typeinfo:eu-repo/semantics/publishedVersion


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