- Crystal Engineering of N,N′-Diphenylurea Compounds Featuring Phenyl-Perfluorophenyl Interaction
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Here, aiming to adopt the phenyl-perfluorophenyl interaction to regulate molecular alignment and arrangement for crystal engineering, we examined and compared in detail the crystal structures of N,N′-diphenylurea compounds 1-6. We found that phenyl-perfluorophenyl interaction greatly influenced the intermolecular arrangement in the crystal, and we were able to prepare a cocrystal of 1 and 2, in which the molecules were alternately arranged under the control of the phenyl-perfluorophenyl interaction. This arrangement was driven by the asymmetric geometry of the hydrogen bonds in the cocrystal (1·2), in which 2, bearing two perfluorophenyl groups, worked as a better hydrogen bond donor. In contrast, NH connected to the phenyl group in 3 proved to be a better hydrogen bond donor due to the intramolecular resonance effect. N,N′-Dimethylated derivatives, 4-6, existed in cis-cis form in the crystal. Antiparallel carbonyl-carbonyl arrangements were observed in 4 and 6, while an unexpected carbonyl-perfluorophenyl interaction was observed in the crystal of 5. These findings will be helpful in the design of diphenylurea-based functional molecules, especially for solid-state application.
- Yamasaki, Ryu,Iida, Mana,Ito, Ai,Fukuda, Kazuo,Tanatani, Aya,Kagechika, Hiroyuki,Masu, Hyuma,Okamoto, Iwao
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- Reactions of N-(perfluorophenyl)carbonimidoyl dichloride with aromatic acids and their derivatives in the presence of AlCl3. Formation of 2-(perfluorophenyl)isoindoline-1,3-dione and its derivatives
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Reactions of N-(perfluorophenyl)carbonimidoyl dichloride with benzoic acid, benzoyl chloride, ethyl benzoate, and also with phthalic acid, phthaloyl dichloride, and phthalic anhydride in the presence of AlCl3 at 170°C afford2-(perfluorophenyl)isoindoline-1,3-dione. With benzoic acid and benzoyl chloride form also 2-(perfluorophenyl)-3-[(perfluorophenyl)imino] isoindolin-1-one. In reactions with compounds of the benzene series arise also derivatives of arylimidoyl chlorides and amide type compounds containing a CONHC6F5 moiety. 2005 Pleiades Publishing, Inc.
- Petrova,Platonov
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p. 218 - 226
(2007/10/03)
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- Reactions of N-(Pentafluorophenyl)carbonimidoyl dichloride with fluorinated benzenes in the presence of AlCl3
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N-(Pentafluorophenyl)carbonimidoyl dichloride (1) reacts, in the presence of excess AlCl3, with fluorinated benzenes containing 1-5 fluorine atoms in the molecule. With fluoro- and 1,3,5-trifluorobenzene the reaction gives the corresponding imi
- Petrova, Tamara D.,Platonov, Vyacheslav E.,Pokrovskii, Leonid M.,Rybalova, Tatyana V.,Gatilov, Yurii V.
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p. 1449 - 1466
(2007/10/03)
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