Mass Spectra of New Heterocycles: XXI. Study of Alkyl [(5-Amino-1H-pyrrol-2-yl)sulfanyl]acetates by Electron and Chemical Ionization Mass Spectrometry

Abstract

The fragmentation of previously inaccessible alkyl [(5-amino-1H-pyrrol-2-yl)sulfanyl]acetates under electron (70 eV) and chemical (reactant gas methane) ionization conditions was studied for the first time. Under electron ionization, all the studied compounds form a molecular ion (Irel 7–100%), the main primary fragmentation pathway of which is associated with the C–S bond cleavage in the sulfanyl group and elimination of the ester fragment (R4OCOCH2) in the form of a radical. The chemical ionization of alkyl [(5-amino-1H-pyrrol-2-yl)sulfanyl]acetates is characterized by protonation, recharging, and electrophilic addition. The base peak belongs to an [M + H]+ ion. Chemical ionization is accompanied by the elimination of an R4OCOCH2 radical from the M+• and [M + Et]+ ions and an R4OCOCHS molecule from the M+• and [M + H]+ ions.

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Notes

  1. 1.

    For m/z 184 (20): total intensity (Irel ion + Irel13C ion A) is given.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences.

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Correspondence to L. V. Klyba.

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For communication XX, see [1].

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Klyba, L.V., Nedolya, N.A., Sanzheeva, E.R. et al. Mass Spectra of New Heterocycles: XXI. Study of Alkyl [(5-Amino-1H-pyrrol-2-yl)sulfanyl]acetates by Electron and Chemical Ionization Mass Spectrometry. Russ J Org Chem 56, 768–774 (2020). https://doi.org/10.1134/S1070428020050073

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Keywords:

  • alkyl [(5-amino-1H-pyrrol-2-yl)sulfanyl]acetates
  • electron and chemical ionization
  • mass spectra
  • molecular ion
  • fragmentation