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Issue 14, 2009
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The conformational landscape of 5-methoxytryptamine studied by rotationally resolved fluorescence spectroscopy and resonant ionization spectroscopy

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Abstract

Rotationally resolved electronic spectra of three different conformers of 5-methoxytryptamine were recorded in a molecular beam. 5-Methoxy substitution reduces the number of observed conformers to three compared to seven that have been reported for tryptamine. Quantum chemical calculations indicate that anti-rotamers of the methoxy-group are more stable relative to the syn-forms. Two gauche structures (Gpy(in) and Gph(in)) of the ethylamino group with respect to the indole chromophore were found to be less stable than the other seven. The lowest electronically excited state has been identified as the 1Lb one for all observed conformers which was confirmed by quantum-chemical calculations. Based on the comparison of rotational constants obtained from fits using evolutionary algorithms with those from calculations, the three observed conformers were determined to be the Gpy(up), Gph(up), Gpy(out) ethylamino side-chain conformations.

Graphical abstract: The conformational landscape of 5-methoxytryptamine studied by rotationally resolved fluorescence spectroscopy and resonant ionization spectroscopy

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Publication details

The article was received on 04 Nov 2008, accepted on 26 Jan 2009 and first published on 16 Feb 2009


Article type: Paper
DOI: 10.1039/B819469F
Citation: Phys. Chem. Chem. Phys., 2009,11, 2433-2440
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    The conformational landscape of 5-methoxytryptamine studied by rotationally resolved fluorescence spectroscopy and resonant ionization spectroscopy

    T. B. C. Vu, I. Kalkman, W. L. Meerts, C. Brand, Y. N. Svartsov, S. Wiedemann, R. Weinkauf and M. Schmitt, Phys. Chem. Chem. Phys., 2009, 11, 2433
    DOI: 10.1039/B819469F

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