IBIMOL   23987
INSTITUTO DE BIOQUIMICA Y MEDICINA MOLECULAR PROFESOR ALBERTO BOVERIS
Unidad Ejecutora - UE
artículos
Título:
Conformational and stereoelectronic investigation of tryptamine. An AIM/NBO study.
Autor/es:
LOBAYAN ROSANA; MARIA C. PEREZ SCHMITH; ALICIA H. JUBERT; ARTURO ALBERTO VITALE
Revista:
JOURNAL OF MOLECULAR MODELING - (Print)
Editorial:
SPRINGER
Referencias:
Lugar: Berlin; Año: 2012 vol. 18 p. 2577 - 2588
ISSN:
1610-2940
Resumen:
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 Baders 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.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.H-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.