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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. (2016). Stability of odd versus even electron gas-phase (quasi)molecular ions derived from pyridine-substituted N-heterotriangulenes. ChemPlusChem, 204-211. doi:10.1002/cplu.201600416.

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cplu201600416-sup-0001-SupMat.docx (Supplementary material), 511KB
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cplu201600416-sup-0001-SupMat.docx
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 Creators:
Hitzenberger, Jakob Felix1, Author
Dral, Pavlo O.2, Author              
Meinhardt, Ute1, Author
Clark, Timothy1, Author
Thiel, Walter2, Author              
Kivala, Milan1, Author
Drewello, Thomas1, Author
Affiliations:
1Friedrich-Alexander-Universitat Erlangen-Nurnberg, Erlangen, GERMANY, ou_persistent22              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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Free keywords: N-heterotriangulenes odd- versus; even-electron ion electrospray; ionization mass spectrometry; collision-induced dissociation; ab initio and DFT calculations
 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: 2016-09-302016-08-122016-10-112016-10-17
 Publication Status: Published online
 Pages: -
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 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: - Sequence Number: - Start / End Page: 204 - 211 Identifier: ISSN: 2192-6506
CoNE: https://pure.mpg.de/cone/journals/resource/2192-6506