Linear ω-phenylalkylamines of increasing alkyl chain length have been investigated employing synchrotron radiation in the photon energy range from 7 to 15 eV. These molecules have received considerable interest because they bear the skeleton of biologically relevant compounds including neurotransmitters and because of the possible interaction between the amino moiety and the phenyl ring. Recently, the contribution of this interaction has been assayed in both neutral and protonated species, pointing to a role of the polymethylene chain length. In this work, the ionization energy (IE) values of benzylamine (BA), 2-phenylethylamine (2-PEA), 3-phenylpropylamine (3-PPA), and 4-phenylbutylamine (4-PBA) were investigated in order to ascertain the impact of the different alkyl chain lengths and to verify an amino radical cation-π interaction. The IEs obtained experimentally, 8.54, 8.37, 8.29, and 8.31 eV for BA, 2-PEA, 3-PPA and 4-PBA, respectively, show a decreasing trend that is discussed employing calculations at the CBS-QB3 level. Moreover, the appearance energy values for major fragments produced by the photofragmentation process are reported.

Photoionization mass spectrometry of ω-phenylalkylamines: Role of radical cation-π interaction / Corinti, Davide; Catone, Daniele; Turchini, Stefano; Rondino, Flaminia; Crestoni, Maria Elisa; Fornarini, Simonetta. - In: THE JOURNAL OF CHEMICAL PHYSICS. - ISSN 0021-9606. - 148:16(2018), p. 164307. [10.1063/1.5027786]

Photoionization mass spectrometry of ω-phenylalkylamines: Role of radical cation-π interaction

Corinti, Davide;Crestoni, Maria Elisa;Fornarini, Simonetta
2018

Abstract

Linear ω-phenylalkylamines of increasing alkyl chain length have been investigated employing synchrotron radiation in the photon energy range from 7 to 15 eV. These molecules have received considerable interest because they bear the skeleton of biologically relevant compounds including neurotransmitters and because of the possible interaction between the amino moiety and the phenyl ring. Recently, the contribution of this interaction has been assayed in both neutral and protonated species, pointing to a role of the polymethylene chain length. In this work, the ionization energy (IE) values of benzylamine (BA), 2-phenylethylamine (2-PEA), 3-phenylpropylamine (3-PPA), and 4-phenylbutylamine (4-PBA) were investigated in order to ascertain the impact of the different alkyl chain lengths and to verify an amino radical cation-π interaction. The IEs obtained experimentally, 8.54, 8.37, 8.29, and 8.31 eV for BA, 2-PEA, 3-PPA and 4-PBA, respectively, show a decreasing trend that is discussed employing calculations at the CBS-QB3 level. Moreover, the appearance energy values for major fragments produced by the photofragmentation process are reported.
2018
photoionization; mass spectrometry; phenylalkylamines; non-covalent interactions; ionization energy
01 Pubblicazione su rivista::01a Articolo in rivista
Photoionization mass spectrometry of ω-phenylalkylamines: Role of radical cation-π interaction / Corinti, Davide; Catone, Daniele; Turchini, Stefano; Rondino, Flaminia; Crestoni, Maria Elisa; Fornarini, Simonetta. - In: THE JOURNAL OF CHEMICAL PHYSICS. - ISSN 0021-9606. - 148:16(2018), p. 164307. [10.1063/1.5027786]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1117856
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