Ion mobility spectrometry of N-methylimidazole and possibilities of its determination

Objectives. To determine the ion mobility of N-methylimidazole, establish the structure of ions corresponding to characteristic signals, and determine the detection limit of N-methylimidazole on the ion-drift detector Kerber.

Methods. Ion mobility spectrometry was used to study the ionization processes. The enthalpies of the reactions of monomer and dimer ions were calculated in the ORCA 4.1.1 software by the B3LYP density functional method with a set of basic functions 6-31G (d, p).

Results. The drift time and ion mobility values of N-methylimidazole were determined. A method for mathematical processing of spectra and a program for its implementation was developed. The changing peculiarities of the ion mobility spectrum during measurement at a given time were studied. According to the interpretation of the spectrum signals, the structure of the generated ions was proposed, and the enthalpies of ion formation were determined.

Conclusions. The characteristic signal of the N-methylimidazole ion protonated at the nitrogen atom of the pyridine type was revealed. It was found that two signals in the ion mobility spectra of N-methylimidazole correspond to the presence of the monomer and dimer ions. The detection limit of N-methylimidazole on the ion-drift detector Kerber was determined, amounting to 3 pg.

1. Eiceman G.A., Kapras Z., Hill H.H. Ion Mobility Spectrometry: 3rd ed. Boca Raton: CRC; 2013. 444 p. https://doi.org/10.1201/b16109

2. Borsdorf H., Eiceman, G.A. Ion mobility spectrometry: Principles and applications. Appl. Spectrosc. Rev. 2006;41(3):323–375. https://doi.org/10.1080/05704920600663469

3. Marquez-Sillero I., Aguilera-Herrador E., Cardenas S., Valcarcel M. Ion-mobility spectrometry for environmental analysis. TrAC Trends in Analytical Chemistry. 2011;30(5):677–690. https://doi.org/10.1016/j.trac.2010.12.007

4. Han H.Y., Wang H.M., Jiang H.H., Stano M., Sabo M., Matejcik S., Chu Y.N. Corona discharge ion mobility spectrometry of ten alcohols. Chinese J. Chem. Phys. 2009;22(6):605–610. https://doi.org/10.1088/16740068/22/06/605-610

5. Tabrizchi M., ILbeigi V. Detection of explosives by positive corona discharge ion mobility spectrometry. J. Hazard. Mater. 2010;176(1–3):692–696. https://doi.org/10.1016/j.jhazmat.2009.11.087

6. Jafari M.T., Khayamian T. Direct determination of ammoniacal nitrogen in water samples using corona discharge ion mobility spectrometry. Talanta. 2008;76(5):1189–1193. https://doi.org/10.1016/j.jhazmat.2009.11.087

7. Jafari M.T., Khayamian T., Shaer V., Zarei N. Determination of veterinary drug residues in chicken meat using corona discharge ion mobility spectrometry. Anal. Chim. Acta. 2007;581(1):147–153. https://doi.org/10.1016/j.aca.2006.08.005

8. Hashemian Z., Mardihallaj A., Khayamian T. Analysis of biogenic amines using corona discharge ion mobility spectrometry. Talanta. 2010;81(3):1081–1087. https://doi.org/10.1016/j.talanta.2010.02.001

9. Mäkinen M.A., Anttalainen O.A., Sillanpää M.E. Ion mobility spectrometry and its applications in detection of chemical warfare agents. Anal. Chem. 2010;82(23):9594–9600. https://doi.org/10.1021/ac100931n

10. Aleksandrova D.A., Melamed T.B., Baberkina E.P., Kovalenko A.E., Kuznetsov Vl.Vit., Kuznetsov Vit. Vl., Fenin A.A., Shaltaeva Yu.R., Belyakov V.V. Ion Mobility Spectrometry of Imidazole and Possibilities of its Determination. J. Anal. Chem. 2021;76(11):1282–1289. https://doi.org/101134/S106193482111002 [Russian Original Text: Aleksandrova D.A., Melamed T.B., Baberkina E.P., Kovalenko A.E., Kuznetsov Vl.Vit., Kuznetsov Vit. Vl., Fenin A.A., Shaltaeva Yu.R., Belyakov V.V. Ion Mobility Spectrometry of Imidazole and Possibilities of its Determination. Zhurnal Analiticheskoi Khimii. 2021;76(11):989–996 (in Russ.). https://doi.org/10.31857/S0044450221110025]

11. Lutz P. Benzimidazole and its derivatives – from fungicides to designer drugs. A new occupational and environmental hazards. Medycyna Pracy. 2012;63(4):505–513.

12. Schoeder C., Hess C., Madea B., et al. Pharmacological evaluation of new constituents of “Spice”: synthetic cannabinoids based on indole, indazole, benzimidazole and carbazole scaffolds. Forensic Toxicol. 2018;36:385–403. https://doi.org/10.1007/s11419-018-0415-z

13. Grishin S.S., Negru K.I., Baberkina E.P., Kovalenko A.E., Gushchina A.A., Aleksandrova D.A., Shutova Y.E., Zharikov A.P., Dorskaya E.V., Shaltaeva Y.R., Belyakov V.V., Golovin A.V., Gromov E.A., Matusko M.A., Khamraev V.F. The influence of chemical structure of nitrogen-containing heterocyclic compounds on the character of ion mobility spectra. J. Phys.: Conf. Series. 2019;498(1):012036. https://doi.org/10.1088/1757-899X/498/1/012036

14. Aleksandrova D.A., Baberkina E.P., Grishin S.S., Gushchina A.A., Kurbanova D.M., Trefilova V.V., Kovalenko A.E., Shaltaeva Yu.R., Belyakov V.V. Study of the ion mobility spectra of nitrogen-containing heterocycles on the ion-drift detector “Kerber.” In: Tezisy dokladov XXII Vseross. konf. molodykh uchenykh-khimikov) (Abstracts of XXII All-Russian Conf. of Young Chemists), Nizhnii Novgorod; 2019. p. 277 (in Russ.).

15. Aleksandrova D.A., Baberkina E.P., Dubkina E.A., Kovalenko A.E., Shaltaeva Yu.R., Belyakov V.V. Investigation of the spectra of ionic mobility of aromatic nitrogencontaining heterocyclic compounds on the ion-drift detector “Kerber.” In: Aktual’nye aspekty khimicheskoi tekhnologii biologicheski aktivnykh veshchestv: sbornik nauchnykh trudov (Actual Aspects of Chemical Technology of Biologically Active Substances: Collection of Scientific Papers). Moscow; 2020. P. 34 (in Russ.).

16. Schofield K., Grim-mett M.R., Keene B.R.T. Heteroaromatic Nitrogen Compounds: The Azoles. Cambridge: Cambridge University Press; 1976. 437 p. 17. Joule J.A., Mills K. Heterocyclic Chemistry, 4th ed. Oxford, U.K.: Blackwell Science; 2000. 608 p.