Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy

Jona Merx; Kas Houthuijs; Hidde Elferink; Eva Witlox; Jasmin Mecinović; Jos Oomens; Jonathan Martens; Thomas Boltje; Floris P J T Rutjes

doi:10.1002/chem.202104078

Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy

Jona Merx, Kas Houthuijs, Hidde Elferink, Eva Witlox, Jasmin Mecinović, Jos Oomens, Jonathan Martens, Thomas Boltje^*, Floris P J T Rutjes^*

^*Corresponding author for this work

Department of Physics, Chemistry and Pharmacy

Radboud University Nijmegen

Research output: Contribution to journal › Journal article › Research › peer-review

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Abstract

N- Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N -acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of the DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N -acyliminium ions.

Original language	English
Article number	e202104078
Journal	Chemistry - A European Journal
Volume	28
Issue number	9
ISSN	1521-3765
DOIs	https://doi.org/10.1002/chem.202104078
Publication status	Published - 16. Feb 2022

Keywords

DFT calculations
N-acyliminium ion
heterocycles
ion spectroscopy
stereoselectivity
Tandem Mass Spectrometry
Molecular Conformation
Spectrophotometry, Infrared/methods
Nitrogen
Ions/chemistry

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10.1002/chem.202104078Licence: CC BY

Open access versionFinal published version, 3.98 MBLicence: CC BY

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title = "Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy",

abstract = "N- Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N -acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of the DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N -acyliminium ions.",

keywords = "DFT calculations, N-acyliminium ion, heterocycles, ion spectroscopy, stereoselectivity, Tandem Mass Spectrometry, Molecular Conformation, Spectrophotometry, Infrared/methods, Nitrogen, Ions/chemistry",

author = "Jona Merx and Kas Houthuijs and Hidde Elferink and Eva Witlox and Jasmin Mecinovi{\'c} and Jos Oomens and Jonathan Martens and Thomas Boltje and Rutjes, {Floris P J T}",

note = "{\textcopyright} 2021 Wiley-VCH GmbH.",

year = "2022",

month = feb,

day = "16",

doi = "10.1002/chem.202104078",

language = "English",

volume = "28",

journal = "Chemistry - A European Journal",

issn = "1521-3765",

publisher = "Wiley",

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TY - JOUR

T1 - Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy

AU - Merx, Jona

AU - Houthuijs, Kas

AU - Elferink, Hidde

AU - Witlox, Eva

AU - Mecinović, Jasmin

AU - Oomens, Jos

AU - Martens, Jonathan

AU - Boltje, Thomas

AU - Rutjes, Floris P J T

PY - 2022/2/16

Y1 - 2022/2/16

N2 - N- Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N -acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of the DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N -acyliminium ions.

AB - N- Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N -acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of the DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N -acyliminium ions.

KW - DFT calculations

KW - N-acyliminium ion

KW - heterocycles

KW - ion spectroscopy

KW - stereoselectivity

KW - Tandem Mass Spectrometry

KW - Molecular Conformation

KW - Spectrophotometry, Infrared/methods

KW - Nitrogen

KW - Ions/chemistry

U2 - 10.1002/chem.202104078

DO - 10.1002/chem.202104078

M3 - Journal article

C2 - 34911145

SN - 1521-3765

VL - 28

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 9

M1 - e202104078

ER -

Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy

Abstract

Keywords

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