IBIMOL   23987
INSTITUTO DE BIOQUIMICA Y MEDICINA MOLECULAR PROFESOR ALBERTO BOVERIS
Unidad Ejecutora - UE
artículos
Título:
Aqueous solvent effects on the
Autor/es:
LOBAYAN ROSANA; MARIA C. PEREZ SCHMIT; ALICIA H. JUBERT; ARTURO ALBERTO VITALE
Revista:
JOURNAL OF MOLECULAR MODELING - (Print)
Editorial:
SPRINGER
Referencias:
Lugar: Berlin; Año: 2012 p. 1 - 17
ISSN:
1610-2940
Resumen:
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 TRAwas 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 Baders 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.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 TRAwas 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 Baders 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.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.