Mass spectrometrical and quantum-chemical study of pentafluorophenylhydrazones.

defluorination heterocyclic hydrazone disruption hydrazones pentafluorophenyhydrazones quantum calculations

Journal

Journal of mass spectrometry : JMS
ISSN: 1096-9888
Titre abrégé: J Mass Spectrom
Pays: England
ID NLM: 9504818

Informations de publication

Date de publication:
Oct 2020
Historique:
received: 09 03 2020
revised: 02 04 2020
accepted: 30 04 2020
entrez: 28 11 2020
pubmed: 29 11 2020
medline: 29 11 2020
Statut: ppublish

Résumé

Twenty-one pentafluorphenylhydrazones have been analyzed by means of tandem mass spectrometry (ESI MS/MS) conditions to compare their fragmentations with those ones obtained from quantum-chemical calculations of the hydrazone moiety depending on the substitution from the aldehyde site. The hydrazone N-N bond is disrupted under such conditions, and these results are in accordance with the facts that an electron-rich particle, such as an anion and or radical in a solution, can cause this disruption and simultaneous defluorination in para-position of the hydrazone part of the molecule.

Identifiants

pubmed: 33247509
doi: 10.1002/jms.4540
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e4540

Subventions

Organisme : Research and Development Agency
ID : APVV-17-0513
Organisme : Research and Development Agency
ID : APVV-17-0513
Organisme : Ministry of Education, Science, Research and Sport of the Slovak Republic
Organisme : European Region Development Funds
ID : ITMS 26230120002
Organisme : Research & Development Operational Program
ID : ITMS 26240220061

Informations de copyright

© 2020 John Wiley & Sons, Ltd.

Références

Wegner HA. Molecular switches. Second edition. Edited by Ben L. Feringa and Wesley R. Browne. Angew Chemie Int Ed. Mar. 2012;51(10):2281-2281. https://doi.org/10.1002/anie.201108931
Su X, Aprahamian I. Hydrazone-based switches, metallo-assemblies and sensors. Chemical Society Reviews. 21-Mar-2014;43(6):1963-1981. https://doi.org/10.1039/c3cs60385g
Černuchová P, Vo-Thanh G, Milata V, Loupy A, Jantová S, Theiszová M. Utilization of 2-ethoxymethylene-3-oxobutanenitrile in the synthesis of heterocycles possessing biological activity. Tetrahedron. May 2005;61(22):5379-5387. https://doi.org/10.1016/j.tet.2005.03.066
Bortňák D, Šoral M, Breza M, Vlčková S, Végh D, Milata V. Study of reactions of pentafluorophenylhydrazine with activated enol ethers. Synthesis of N-pentafluorophenylpyrazoles. Arkivoc. 2017;ii: 446-456. https://doi.org/10.24820/ark.5550190.p009.659
Bortňák D, Milata V, Šofranko J, et al. On the formation of uncommon pyrazoloazepines from 5-aminopyrazoles as by-products in the Clauson-Kaas reaction. J Mol Struct. 2018;1166:243-251. https://doi.org/10.1016/j.molstruc.2018.04.034
Brahmachari G, Karmakar I. sp2-C-H Acetoxylation of diversely substituted (E)-1-(Arylmethylene)-2-phenylhydrazines using PhI (OAc)2 as Acetoxy source at ambient conditions. European J Org Chem. 2019;2019(34):5925-5933. https://doi.org/10.1002/ejoc.201900994
Eloh K, Demurtas M, Deplano A, et al. In vitro nematicidal activity of aryl Hydrazones and comparative GC-MS metabolomics analysis. J Agric Food Chem. 2015;63(45):9970-9976. https://doi.org/10.1021/acs.jafc.5b04815
Khan M, Ahad G, Manaf A, et al. Synthesis, in vitro urease inhibitory activity, and molecular docking studies of (perfluorophenyl)hydrazone derivatives. Med Chem Res. 2019;28(6):873-883. https://doi.org/10.1007/s00044-019-02341-5
Bortňák D, Milata V, Šofranko J, et al. Unexpected cleavage of N-N bonds of pentafluorophenylhydrazones-formation of nitriles by a novel fragmentation reaction. ChemistrySelect. 2020;5(13):3929-3933. In press.
Beverina L, Drees M, Facchetti A, Salamone M, Ruffo R, Pagani GA. Bulk heterojunction solar cells-tuning of the HOMO and LUMO energy levels of pyrrolic squaraine dyes. European J Org Chem. Oct. 2011;2011(28):5555-5563. https://doi.org/10.1002/ejoc.201100940
Lukeš V, Michalík M, Poliak P, D. Cagardová “Theoretical and experimental study of model oligothiophenes containing 1-methylene-2-(perfluorophenyl)hydrazine terminal unit,” Synth Met, vol. 219, pp. 83-92, 2016. https://doi.org/10.1016/j.synthmet.2016.05.010
Chan W, Chen B, Wang L, Taghizadeh K, Demott MS, Dedon PC. Quantification of the 2-deoxyribonolactone and nucleoside 5′-aldehyde products of 2-deoxyribose oxidation in DNA and cells by isotope-dilution gas chromatography mass spectrometry: differential effects of γ-radiation and Fe2+−EDTA. J am Chem Soc. 2010;132(17):6145-6153. https://doi.org/10.1021/ja910928n
Keana JFW, Cai SX. New reagents for photoaffinity labeling: synthesis and photolysis of functionalized perfluorophenyl azides. J Org Chem. 1990;55(11):3640-3647. https://doi.org/10.1021/jo00298a048
Weaver J, Senaweera S. C-F activation and functionalization of perfluoro- and polyfluoroarenes. Tetrahedron. 2014;70(41):7413-7428. https://doi.org/10.1016/j.tet.2014.06.004
Pažitný A, Solčán T, Végh D. Pentafluorobenzaldehyde and its utilizing in organic synthesis. Journal of Fluorine Chemistry. Mar-2009;130(3):267-294. https://doi.org/10.1016/j.jfluchem.2008.12.013
Perašínová L, Svoboda I, Végh D, Solčan T, Kožíšek J. 1,2,4,5-Tetrafluoro-3,6-bis (nitromethyl)benzene. Acta Crystallogr Sect E Struct Reports Online. May 2006;62(5):o1689-o1690. https://doi.org/10.1107/S1600536806011561
Zhang Z, Zhou W. Arylation of nitromethane: masked nucleophilic formylation of fluoroquinolones. Tetrahedron Lett. May 2005;46(22):3855-3858. https://doi.org/10.1016/j.tetlet.2005.03.181
Day JI, Weaver JD. Selective and scalable perfluoroarylation of nitroalkanes. J Org Chem. Jul. 2017;82(13):6801-6810. https://doi.org/10.1021/acs.joc.7b00962
Timperley CM, Banks RE, Young IM, Haszeldine RN. Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning. J Fluor Chem. Aug. 2011;132(8):541-547. https://doi.org/10.1016/j.jfluchem.2011.05.028
Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Weinheim: Wiley; 2004.
Becke D. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. Apr. 1993;98(7):5648-5652. https://doi.org/10.1063/1.464913
Dunning TH. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen. J Chem Phys. Jan. 1989;90(2):1007-1023. https://doi.org/10.1063/1.456153
Frisch JMJ, Trucks GW, Schlegel HB, et al. Gaussian 16, Revision B.01. Wallingford CT: Gaussian, Inc.; 2016.
Ugliengo P. "MOLDRAW: a Program to Display and Manipulate Molecular and Crystal Structures", University Torino, Torino 2006. Available from: http://www.moldraw.unito.it
Wright P, Alex A, Pullen F. Predicting collision-induced dissociation spectra: semi-empirical calculations as a rapid and effective tool in software-aided mass spectral interpretation. Rapid Commun Mass Spectrom. 2014;28:1127-1143. https://doi.org/10.1002/rcm.6870
Wright P, Alex A, Pullen F. Predicting collision-induced dissociation mass spectra: understanding the role of the mobile proton in small molecule fragmentation. Rapid Commun Mass Spectrom. 2016;30(9):1163-1175. https://doi.org/10.1002/rcm.7521
Tureček F. The basics of gas-phase ion chemistry. Chem Listy. 2020;114(2):89-95.

Auteurs

Dušan Bortňák (D)

Department of Organic Chemistry, Slovak Technical University, Radlinského 9, Bratislava, SK-812 37, Slovakia.

Daniel Pecher (D)

Toxicological and Antidoping Center, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, Bratislava, SK-832 32, Slovakia.

Daniel Végh (D)

Department of Organic Chemistry, Slovak Technical University, Radlinského 9, Bratislava, SK-812 37, Slovakia.

Martin Breza (M)

Department of Physical Chemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, Bratislava, SK-812 37, Slovakia.

Peter Mikuš (P)

Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, Bratislava, SK-832 32, Slovakia.

Viktor Milata (V)

Department of Organic Chemistry, Slovak Technical University, Radlinského 9, Bratislava, SK-812 37, Slovakia.

Classifications MeSH