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  Stability of Odd- Versus Even-Electron Gas-Phase (Quasi)Molecular Ions Derived from Pyridine-Substituted N-Heterotriangulenes

Hitzenberger, J. F., Dral, P. O., Meinhardt, U., Clark, T., Thiel, W., Kivala, M., et al. (2017). Stability of Odd- Versus Even-Electron Gas-Phase (Quasi)Molecular Ions Derived from Pyridine-Substituted N-Heterotriangulenes. ChemPlusChem, 82(2), 204-211. doi:10.1002/cplu.201600416.

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 Creators:
Hitzenberger, Jakob F.1, Author
Dral, Pavlo O.2, Author              
Meinhardt, Ute3, Author
Clark, Timothy4, Author
Thiel, Walter2, Author              
Kivala, Milan3, Author
Drewello, Thomas1, Author
Affiliations:
1Physical Chemistry I, Department of Chemistry and Pharmacy Friedrich-Alexander University Erlangen-Nürnberg (FAU), Egerlandstrasse 3, 91058 Erlangen (Germany), ou_persistent22              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
3Organic Chemistry I, Department of Chemistry and Pharmacy Friedrich-Alexander University Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen (Germany), ou_persistent22              
4Computer-Chemie-Centrum, Department of Chemistry and Pharmacy Friedrich-Alexander University Erlangen-Nürnberg (FAU), Nägelbachstrasse 25, 91052 Erlangen (Germany), ou_persistent22              

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Free keywords: ab initio calculations; collision-induced dissociation; density functional calculations; electrospray ionisation; mass spectrometry; N-heterotriangulenes
 Abstract: Electrospray ionisation of N-heterotriangulenes (i.e., dimethylmethylene-bridged triphenylamines) with up to three pyridyl groups at their periphery, produces the true radical cation ([M]+•) and the protonated molecule ([M+H]+) simultaneously. These ions are studied as model systems to illustrate the stability alternation of odd- versus even-electron ions in energy-dependent collision-induced dissociation (CID) experiments. All ions show the same fragmentation pattern, the consecutive loss of three methyl radicals (•CH3) from the dimethylmethylene bridges of the central triangulene core. [M]+• ions dissociate at much lower collision energies than their [M+H]+ counterparts. The radical cation forms a singlet fragment with an extended aromatic system that is energetically favoured. Ab initio and density functional theory calculations support this interpretation and allow the assignment of the electronic structure of the fragment ions. Consecutive collision-induced dissociations provide a better match with theory when studied with an ion trap, rather than a linear quadrupole. This is attributed to the resonant nature of the excitation of intermediate ions.

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Language(s): eng - English
 Dates: 2016-10-112016-08-162016-10-172016-11-222017-02
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/cplu.201600416
 Degree: -

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Title: ChemPlusChem
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 82 (2) Sequence Number: - Start / End Page: 204 - 211 Identifier: ISSN: 2192-6506
CoNE: https://pure.mpg.de/cone/journals/resource/2192-6506