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Low-energy electron-induced dissociation in gas-phase nicotine, pyridine, and methyl-pyrrolidine

Journal Article · · Journal of Chemical Physics
DOI:https://doi.org/10.1063/1.4994679· OSTI ID:1474073
 [1];  [2];  [3];  [3]
  1. Univ. of Notre Dame, IN (United States). Radiation Lab.; Radiation Laboratory, University of Notre Dame, Notre Dame, Indiana 46556
  2. Univ. of Saskatchewan, Saskatoon, SK (Canada). Dept. of Medical Imaging, College of Medicine
  3. Univ. of Notre Dame, IN (United States). Radiation Lab., and Dept. of Physics
+ Show Author Affiliations

Dissociative electron attachment to nicotine, pyridine, and N-methyl-pyrrolidine was studied in the gas phase in order to assess their stability with respect to low-energy electron interactions. Anion yield curves for different products at electron energies ranging from zero to 15 eV were measured, and the molecular fragmentation pathways were proposed. Nicotine does not form a stable parent anion or a dehydrogenated anion, contrary to other biological systems. However, we have observed complex dissociation pathways involving fragmentation at the pyrrolidine side accompanied by isomerization mechanisms. Combining structure optimization and enthalpy calculations, performed with the Gaussian09 package, with the comparison with a deuterium-labeled N-methyl-d3-pyrrolidine allowed for the determination of the fragmentation pathways. In contrast to nicotine and N-methylpyrrolidine, the dominant pathway in dissociative electron attachment to pyridine is the loss of hydrogen, leading to the formation of an [M-H]- anion. The presented results provide important new information about the stability of nicotine and its constituent parts and contribute to a better understanding of the fragmentation mechanisms and their effects on the biological environment.

Research Organization:
Univ. of Notre Dame, IN (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Grant/Contract Number:
FC02-04ER15533
OSTI ID:
1474073
Alternate ID(s):
OSTI ID: 1378423
Journal Information:
Journal of Chemical Physics, Journal Name: Journal of Chemical Physics Journal Issue: 9 Vol. 147; ISSN 0021-9606
Publisher:
American Institute of Physics (AIP)Copyright Statement
Country of Publication:
United States
Language:
English

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Cited By (4)

Selecting and identifying gas-phase protonation isomers of nicotineH + using combined laser, ion mobility and mass spectrometry techniques journal January 2019
Low-energy electron collisions with proline and pyrrolidine: A comparative study journal February 2018
Cross sections for electron collision with pyridine [C 5 H 5 N] molecule journal September 2018
Cross sections for electron collision with pyridine [C$_{5}$H$_{5}$N] molecule text January 2018

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