5-Hydroxytryptamine (serotonin) was geometry optimized at the
B3YP/6-31G(d) level of theory to determine the energetically most
favourable conformations of the aromatic hydroxyl group and the
protonated ethylamine side chain. The hydroxyl group was found to be
most stable at anti for all conformations, and the two lowest energy
gas phase conformers found were: chi(2) = g(+), chi(3) = g(-) and
chi(2) = g(-), chi(3) = g(+). The protonated amino group was found
equally stable at g+, g- and anti. The transition structures linking
each gas phase minimum were also computed. Minima found were subjected
to solvation calculations in chloroform, DMSO, ethanol and water, which
shifted their relative stabilities. (C) 2002 Elsevier Science B.V. All
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