Electron Transfer Induced Decomposition in Potassium–Nitroimidazoles Collisions: An Experimental and Theoretical Work
Abstract
:1. Introduction
2. Results and Discussion
2.1. Nitroimidazoles and Methylated Compounds
2.1.1. Parent Anion Formation
2.1.2. Formation of NO2−, Loss of Neutral NO2, and Related Multiple Dehydrogenation (HNO2−, H2NO2−, and H3NO2−)
2.1.3. (M–NO)‒ and (M–OH)‒ Formation
2.1.4. CN− Formation
2.2. Imidazole Molecule
2.2.1. (IMI−H)− Formation
2.2.2. C2H2N−, CH− and CN− Formation
3. Experimental Methods
4. Theoretical Method
5. Conclusions
Supplementary Materials
Supplementary File 1Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
DEA | dissociative electron attachment |
SMC | Schwinger multichannel |
IMI | imidazole |
4(5)NI | 4(5)-nitroimidazole |
2NI | 2-nitroimidazole |
Me4NI | 1-methyl-4-nitroimidazole |
Me5NI | 1-methyl-5-nitroimidazole |
VAE | vertical attachment energy |
TOF | time-of-flight |
BR | branching ratio |
TNI | temporary negative ion |
MO | molecular orbital |
DBS | dipole bound state |
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m/z | 4(5)NI | 2NI | Me4NI | Me5NI | IMI |
---|---|---|---|---|---|
1 | H− | H− | H− | H− | H− |
12 | C− | ||||
13 | CH− | CH− | |||
14 | CH2− | ||||
15 | CH3−/NH− | CH3−/NH− | |||
16 | O−/NH2− | O−/NH2− | O−/NH2− | O−/NH2− | O−/NH2− |
17 | OH− | OH− | OH− | OH− | |
24 | C2− | C2− | C2− | ||
25 | C2H− | C2H− | C2H− | C2H− | |
26 | CN− | CN− | CN− | CN− | CN− |
39 | C2HN−/C3H3− | C2HN−/C3H3− | C2HN−/C3H3− | C2HN−/C3H3− | |
40 | C2H2N− | C2H2N− | C2H2N− | C2H2N− | C2H2N− |
41 | C2H3N−/CHN− | ||||
42 | CNO−/CH2N− | CNO−/CH2N− | CNO−/CH2N− | CNO−/CH2N− | |
46 | NO2− | NO2− | NO2− | NO2− | |
50 | C3N− | ||||
64 | (4(5)NI–H3NO2)− | ||||
65 | (4(5)NI–H2NO2)− | ||||
66 | (4(5)NI–HNO2)− | (2NI–HNO2)− | (Me4NI–CH3NO2)− | (Me5NI–CH3NO2)− | |
67 | (4(5)NI–NO2)− | (2NI–NO2)− | (IMI–H)− | ||
68 | (IMI–H)− * | ||||
81 | (Me4NI–NO2)− | (Me5NI–NO2)− | |||
82 | (4(5)NI–HNO)− | (Me4NI–CH3NO)− | (Me5NI–CH3NO)− | ||
83 | (4(5)NI–NO)− | (2NI–NO)− | |||
96 | (4(5)NI–OH)− | (2NI–OH)− | (Me4NI–HNO)− | (Me5NI–HNO)− | |
112 | (4(5)NI–H)− | (2NI–H)− | (Me4NI–CH3)− | (Me5NI–CH3)− | |
113 | 4(5)NI− | 2NI− | |||
114 | 4(5)NI− * | ||||
127 | Me4NI− | Me5NI− | |||
128 | Me4NI− * | Me5NI− * |
IMI | 2NI | 4NI | Me4NI | Me5NI |
---|---|---|---|---|
HOMO πC=C −9.3 eV | HOMO πC=C −10.4 eV | HOMO πC=N −11.8 eV | HOMO πC=N −11.4 eV | HOMO πC=N/C=C −11.4 eV |
LUMO π*ring 5.2 eV | LUMO π*ring 4.9 eV | LUMO σ*C=C 6.5 eV | LUMO σ*C=C 7.3 eV | LUMO σ*C=C 8.9 eV |
π*C=C 7.2 eV | π*C=C 6.1 eV | π*C=C 10.9 eV | π*C=C 11.3 eV | π*C=C 11.7 eV |
π*CH 8.3 eV | π*CH 7.4 eV | π*C=C 13.2 eV | π*C=C 14.9 eV | π*C=C 15.4 eV |
σ*CH 10.1 eV | σ*CH 9.0 eV |
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Mendes, M.; García, G.; Bacchus-Montabonel, M.-C.; Limão-Vieira, P. Electron Transfer Induced Decomposition in Potassium–Nitroimidazoles Collisions: An Experimental and Theoretical Work. Int. J. Mol. Sci. 2019, 20, 6170. https://doi.org/10.3390/ijms20246170
Mendes M, García G, Bacchus-Montabonel M-C, Limão-Vieira P. Electron Transfer Induced Decomposition in Potassium–Nitroimidazoles Collisions: An Experimental and Theoretical Work. International Journal of Molecular Sciences. 2019; 20(24):6170. https://doi.org/10.3390/ijms20246170
Chicago/Turabian StyleMendes, Mónica, Gustavo García, Marie-Christine Bacchus-Montabonel, and Paulo Limão-Vieira. 2019. "Electron Transfer Induced Decomposition in Potassium–Nitroimidazoles Collisions: An Experimental and Theoretical Work" International Journal of Molecular Sciences 20, no. 24: 6170. https://doi.org/10.3390/ijms20246170