Synthesis and crystal structures of five fluorinated diphenidine derivatives

Mewis, RE, Hulme, MC, Marron, J, Langley, SK, Sutcliffe, OB and Benjamin, SL ORCID: https://orcid.org/0000-0002-5038-1599, 2025. Synthesis and crystal structures of five fluorinated diphenidine derivatives. Acta Crystallographica Section E: Crystallographic Communications, 81 (3): E81. ISSN 2056-9890

Preview

Text 2386432_Benjamin.pdf - Published version Download (3MB) | Preview

Abstract

Diphenidine (1a), a dissociative anaesthetic, was first reported in 2013. Since then, a number of derivatives e.g. 2-methoxphenidine (1b) have been produced by clandestine laboratories and sold as research chemicals. Fluorinated diphenidines, namely, [1-(2,6-difluorophenyl)-2-phenylethyl]dimethylazanium chloride, C16H18F2N+·Cl−, (I), [1-(2,6-difluorophenyl)-2-phenylethyl](ethyl)azanium chloride dichloromethane hemisolvate, 2C16H18F2N+·2Cl−·CH2Cl2, (II), tert-butyl[1-(2,6-difluorophenyl)-2-phenylethyl]azanium chloride, C18H22F2N+·Cl−, (III), 1-[1-(2,6-difluorophenyl)-2-phenylethyl]pyrrolidin-1-ium chloride, C18H20F2N+·Cl−, (IV), and 1-[1-(2,3,4,5,6-pentafluorophenyl)-2-phenylethyl]piperidin-1-ium chloride, C19H19F5N+·Cl−, (V), were synthesized and structurally characterized by 1H, 13C and 19F NMR spectroscopy, and single-crystal X-ray diffraction. All five structures exhibit hydrogen bonding between the quaternary amine hydrogen atoms and the chlorine. The N—H⋯Cl distances for (II) and (III) range from 2.21 to 2.31 Å, whereas (I), (IV) and (V) exhibit shorter N—H⋯Cl distances (2.07–2.20 Å). Compounds (IV) and (V) include pyrrolidine and piperidine rings, respectively; the pyrrolidine ring adopts an envelope conformation whereas the piperidine ring adopts a chair conformation. The crystal packing in compounds (I)–(V) is characterized by C—H⋯π interactions; no π–π interactions are observed.

Item Type:	Journal article
Publication Title:	Acta Crystallographica Section E: Crystallographic Communications
Creators:	Mewis, R.E., Hulme, M.C., Marron, J., Langley, S.K., Sutcliffe, O.B. and Benjamin, S.L.
Publisher:	International Union of Crystallography (IUCr)
Date:	March 2025
Volume:	81
Number:	3
ISSN:	2056-9890
Identifiers:	Number Type 10.1107/S2056989025001288 DOI 2386432 Other
Rights:	© 2025 Mewis et al. This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Divisions:	Schools > School of Science and Technology
Record created by:	Melissa Cornwell
Date Added:	26 Feb 2025 10:11
Last Modified:	26 Feb 2025 10:11
URI:	https://irep.ntu.ac.uk/id/eprint/53137

Actions (login required)

Edit View

Statistics

Views

Downloads