Structural Selection by Microsolvation: Conformational
Locking of Tryptamine
Posted on 2005-07-27 - 00:00
The conformational space of tryptamine has been thoroughly investigated using rotationally
resolved laser-induced fluorescence spectroscopy. Six conformers could be identified on the basis of the
inertial parameters of several deuterated isotopomers. Upon attaching a single water molecule, the
conformational space collapses into a single conformer. For the hydrogen-bonded water cluster, this
conformer is identified unambiguously as tryptamine A. In the complex, the water molecule acts as proton
donor with respect to the amino group. An additional interaction with one of the aromatic C−H bonds
selectively stabilizes the observed conformer more than all other conformers. Ab initio calculations confirm
much larger energy differences between the conformers of the water complex than between those of the
monomers.
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Schmitt, Michael; Böhm, Marcel; Ratzer, Christian; Vu, Chau; Kalkman, Ivo; Meerts, W. Leo (2016). Structural Selection by Microsolvation: Conformational
Locking of Tryptamine. ACS Publications. Collection. https://doi.org/10.1021/ja0522377
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AUTHORS (6)
MS
Michael Schmitt
MB
Marcel Böhm
CR
Christian Ratzer
CV
Chau Vu
IK
Ivo Kalkman
WM
W. Leo Meerts