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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Abstract

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.

Abstract
Document type
Article
Creators
CreatorsAffiliationORCID
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
Keywords
rotational spectroscopy, quantum chemical calculations, atom in molecules theory, molecular structure, hydrogen bond, N-methyl-2-aminoethanol, 1,2-aminoalcohols, adrenergic neurotransmitters
Subjects
DOI
https://doi.org/10.3389/fchem.2018.00025
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
URI

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