Corrole isomers: Intrinsic gas-phase shapes via traveling wave ion mobility mass spectrometry and dissociation chemistries via tandem mass spectrometry

Maíra Fasciotti, Alexandre F. Gomes, Fabio C. Gozzo, Bernardo A. Iglesias, Gilberto F. De Sá, Romeu J. Daroda, Motoki Toganoh, Hiroyuki Furuta, Koiti Araki, Marcos N. Eberlin

Research output: Contribution to journalArticle

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Abstract

Corrole and four of its isomers with subtle structural changes promoted by exchange of nitrogen and carbon atoms in the corrole ring have been studied by traveling wave ion mobility mass spectrometry and collision induced dissociation experiments. Significant differences in shapes and charge distributions for their protonated molecules were found to lead to contrasting gas phase mobilities, most particularly for corrorin, the most "confused" isomer. Accordingly, corrorin was predicted by B3LYP/6-31g(d,p) and collisional cross section calculations to display the most compact tri-dimensional structure, whereas NCC4 and corrole were found to be the most planar isomers. Better resolution between the corrole isomers was achieved using the more polarizable and massive CO 2 as the drift gas. Sequential losses of HF molecules were found to dominate the dissociation chemistry of the protonated molecules of these corrole isomers, but their unique structures caused contrasting labilities towards CID, whereas NCC4 showed a peculiar and structurally diagnostic loss of NH 3, allowing its prompt differentiation from the other isomers.

Original languageEnglish
Pages (from-to)8396-8402
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number42
DOIs
Publication statusPublished - Nov 14 2012

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Tandem Mass Spectrometry
traveling waves
Isomers
Mass spectrometry
Mass Spectrometry
mass spectroscopy
isomers
Gases
dissociation
Ions
chemistry
vapor phases
ions
Molecules
charge injection devices
molecules
Carbon Monoxide
Charge distribution
Nitrogen
Carbon

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Corrole isomers : Intrinsic gas-phase shapes via traveling wave ion mobility mass spectrometry and dissociation chemistries via tandem mass spectrometry. / Fasciotti, Maíra; Gomes, Alexandre F.; Gozzo, Fabio C.; Iglesias, Bernardo A.; De Sá, Gilberto F.; Daroda, Romeu J.; Toganoh, Motoki; Furuta, Hiroyuki; Araki, Koiti; Eberlin, Marcos N.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 42, 14.11.2012, p. 8396-8402.

Research output: Contribution to journalArticle

Fasciotti, Maíra ; Gomes, Alexandre F. ; Gozzo, Fabio C. ; Iglesias, Bernardo A. ; De Sá, Gilberto F. ; Daroda, Romeu J. ; Toganoh, Motoki ; Furuta, Hiroyuki ; Araki, Koiti ; Eberlin, Marcos N. / Corrole isomers : Intrinsic gas-phase shapes via traveling wave ion mobility mass spectrometry and dissociation chemistries via tandem mass spectrometry. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10, No. 42. pp. 8396-8402.
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