Rotational Spectrum and Conformational Analysis of N-Methyl-2-Aminoethanol: Insights into the Shape of Adrenergic Neurotransmitters

Calabrese, Camilla ; Maris, Assimo ; Evangelisti, Luca ; Piras, Anna ; Parravicini, Valentina ; Melandri, Sonia (2018) Rotational Spectrum and Conformational Analysis of N-Methyl-2-Aminoethanol: Insights into the Shape of Adrenergic Neurotransmitters. Frontiers in Chemistry, 6 .
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We describe an experimental and quantum chemical study for the accurate determination of the conformational space of small molecular systems governed by intramolecular non-covalent interactions. The model systems investigated belong to the biological relevant aminoalcohol’s family, and include 2-amino-1-phenylethanol, 2-methylamino-1-phenylethanol, noradrenaline, adrenaline 2-aminoethanol, and N-methyl-2-aminoethanol. For the latter molecule, the rotational spectrum in the 6–18 and 59.6–74.4 GHz ranges was recorded in the isolated conditions of a free jet expansion. Based on the analysis of the rotational spectra, two different conformational species and 11 isotopologues were observed and their spectroscopic constants, including 14N-nuclear hyperfine coupling constants and methyl internal rotation barriers, were determined. From the experimental data a structural determination was performed, which was also used to benchmark accurate quantum chemical calculations on the whole conformational space. Atom in molecules and non-covalent interactions theories allowed the characterization of the position of the intramolecular non-covalent interactions and the energies involved, highlighting the subtle balance responsible of the stabilization of all the molecular systems.

Document type
Calabrese, CamillaUniversity of Bologna
Maris, AssimoUniversity of Bologna0000-0003-2644-0023
Evangelisti, LucaUniversity of Bologna0000-0001-9119-1057
Piras, AnnaUniversity of Bologna
Parravicini, ValentinaUniversity of Bologna
Melandri, SoniaUniversity of Bologna0000-0002-0410-5833
rotational spectroscopy, quantum chemical calculations, atom in molecules theory, molecular structure, hydrogen bond, N-methyl-2-aminoethanol, 1,2-aminoalcohols, adrenergic neurotransmitters
Deposit date
22 Feb 2018 11:12
Last modified
23 May 2019 08:33
Project name
MWSPEC - New trends in microwave spectroscopy
Funding program
EC - FP7

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