Mewis Ryan E, Hulme Matthew C, Marron Jack, Langley Stuart K, Sutcliffe Oliver B, Benjamin Sophie L
Department of Natural Sciences, Manchester Metropolitan University, John Dalton Building, Chester St., Manchester, M1 5GD, United Kingdom.
School of Science and Technology, Nottingham Trent University, Nottingham NG11, 8NS, United Kingdom.
Acta Crystallogr E Crystallogr Commun. 2025 Feb 14;81(Pt 3):229-234. doi: 10.1107/S2056989025001288. eCollection 2025 Mar 1.
Diphenidine (), a dissociative anaesthetic, was first reported in 2013. Since then, a number of derivatives 2-methoxphenidine () have been produced by clandestine laboratories and sold as . Fluorinated diphenidines, namely, [1-(2,6-di-fluoro-phen-yl)-2-phenyl-eth-yl]di-methyl-aza-nium chloride, CHFN·Cl, (), 1-(2,6-di-fluoro-phen-yl)-2-phenyl-eth-ylaza-nium chloride di-chloro-methane hemisolvate, 2CHFN·2Cl·CHCl, (), -but-yl[1-(2,6-di-fluoro-phen-yl)-2-phenyl-eth-yl]aza-nium chloride, CHFN·Cl, (), 1-[1-(2,6-di-fluoro-phen-yl)-2-phenyl-eth-yl]pyrrolidin-1-ium chloride, CHFN·Cl, (), and 1-[1-(2,3,4,5,6-penta-fluoro-phen-yl)-2-phenyl-eth-yl]piperidin-1-ium chloride, CHFN·Cl, (), were synthesized and structurally characterized by H, C and F 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 () and () range from 2.21 to 2.31 Å, whereas (), () and () exhibit shorter N-H⋯Cl distances (2.07-2.20 Å). Compounds () and () 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 ()-() is characterized by C-H⋯π inter-actions; no π-π inter-actions are observed.
二苯乙胺（），一种分离麻醉剂，于2013年首次被报道。从那时起，一些衍生物2-甲氧基苯乙胺（）已被秘密实验室生产并作为出售。合成了含氟二苯乙胺，即[1-(2,6-二氟苯基)-2-苯基乙基]二甲基氯化铵，CHFN·Cl，（），1-(2,6-二氟苯基)-2-苯基乙基氯化铵二氯甲烷半溶剂化物，2CHFN·2Cl·CHCl，（），-丁基[1-(2,6-二氟苯基)-2-苯基乙基]氯化铵，CHFN·Cl，（），1-[1-(2,6-二氟苯基)-2-苯基乙基]吡咯烷-1-氯化铵，CHFN·Cl，（），以及1-[1-(2,3,4,5,6-五氟苯基)-2-苯基乙基]哌啶-1-氯化铵，CHFN·Cl，（），并通过氢、碳和氟核磁共振光谱以及单晶X射线衍射对其结构进行了表征。所有五种结构在季铵氢原子和氯之间都表现出氢键作用。（）和（）的N-H⋯Cl距离范围为2.21至2.31 Å，而（）、（）和（）的N-H⋯Cl距离较短（2.07 - 2.20 Å）。化合物（）和（）分别包含吡咯烷环和哌啶环；吡咯烷环呈信封构象，而哌啶环呈椅式构象。化合物（） - （）中的晶体堆积以C-H⋯π相互作用为特征；未观察到π-π相互作用。
