Hydrogen bond-directed cocrystallization and molecular recognition properties of diarylureas

Margaret C. Etter, Zofia Urbanczyk-Lipkowska, Mohammad Zia-Ebrahimi, Thomas W. Panunto

J. Am. Chem. Soc., 1990, 112 (23), pp 8415–8426

DOI: 10.1021/ja00179a028

Publication Date: November 1990

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Controlling Molecular Crystal Polymorphism with Self-Assembled Monolayer Templates
Rupa Hiremath, Joseph A. Basile, Stephen W. Varney, and Jennifer A. Swift
Journal of the American Chemical Society 2005 127 (51), 18321-18327
Abstract | Full Text HTML | PDF | PDF w/ Links
Groth's Original Concomitant Polymorphs Revisited
Michal Rafilovich, Joel Bernstein, Robin K. Harris, David C. Apperley, Panagiotis G. Karamertzanis, and Sarah L. Price
Crystal Growth & Design 2005 5 (6), 2197-2209
Abstract | Full Text HTML | PDF | PDF w/ Links
Crystal Engineering with Bis(thiourea) Derivatives
Gary L. Succaw, Timothy J. R. Weakley, Fusan Han, and Kenneth M. Doxsee
Crystal Growth & Design 2005 5 (6), 2288-2298
Abstract | Full Text HTML | PDF | PDF w/ Links
Chiral Binaphthyl-Derived Amine-Thiourea Organocatalyst-Promoted Asymmetric Morita−Baylis−Hillman Reaction
Jian Wang, Hao Li, Xinhong Yu, Liansuo Zu, and Wei Wang
Organic Letters 2005 7 (19), 4293-4296
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Synthesis and Characterization of Segmented Copoly(ether urea)s with Uniform Hard Segments
Ron M. Versteegen, Rint P. Sijbesma, and E. W. Meijer
Macromolecules 2005 38 (8), 3176-3184
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Molecular Recognition in a Thermoplastic Elastomer
Rolf A. Koevoets, Ron M. Versteegen, Huub Kooijman, Anthony L. Spek, Rint P. Sijbesma, and E. W. Meijer
Journal of the American Chemical Society 2005 127 (9), 2999-3003
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Hydrogen Bonded Dimers of Triurea Derivatives of Triphenylmethanes
Yuliya Rudzevich, Valentyn Rudzevich, Dieter Schollmeyer, Iris Thondorf, and Volker Böhmer
Organic Letters 2005 7 (4), 613-616
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Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea
Tomotaka Okino, Yasutaka Hoashi, Tomihiro Furukawa, Xuenong Xu, and Yoshiji Takemoto
Journal of the American Chemical Society 2005 127 (1), 119-125
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Nature of Urea−Fluoride Interaction: Incipient and Definitive Proton Transfer
Massimo Boiocchi, Laura Del Boca, David Esteban Gómez, Luigi Fabbrizzi, Maurizio Licchelli, and Enrico Monzani
Journal of the American Chemical Society 2004 126 (50), 16507-16514
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Polymorphism in Piroxicam
Agam R. Sheth, Simon Bates, Francis X. Muller, and David J. W. Grant
Crystal Growth & Design 2004 4 (6), 1091-1098
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Enantioselective Aza-Henry Reaction Catalyzed by a Bifunctional Organocatalyst
Tomotaka Okino, Satoru Nakamura, Tomihiro Furukawa, and Yoshiji Takemoto
Organic Letters 2004 6 (4), 625-627
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Efficient Synthesis of Polysubstituted Acylguanidines and Guanylureas
Alan R. Katritzky, Boris V. Rogovoy, Xiaohong Cai, Nataliya Kirichenko, and Katherine V. Kovalenko
The Journal of Organic Chemistry 2004 69 (2), 309-313
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Self-Assembled Nanotubes that Reversibly Bind Acetic Acid Guests
Linda S. Shimizu, Andrew D. Hughes, Mark D. Smith, Matthew J. Davis, B. Paul Zhang, Hans-Conrad zur Loye, and Ken D. Shimizu
Journal of the American Chemical Society 2003 125 (49), 14972-14973
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Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts
Tomotaka Okino, Yasutaka Hoashi, and Yoshiji Takemoto
Journal of the American Chemical Society 2003 125 (42), 12672-12673
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Self-Assembly of Dipeptidyl Ureas: A New Class of Hydrogen-Bonded Molecular Duplexes
Toshiyuki Moriuchi, Takashi Tamura, and Toshikazu Hirao
Journal of the American Chemical Society 2002 124 (32), 9356-9357
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Effect of Solvation on Induce-Fit Molecular Recognition in Supercritical Fluid to Organic Crystals Immobilized on a Quartz Crystal Microbalance
Masanobu Naito, Yusuke Sasaki, Takehisa Dewa, Yasuhiro Aoyama, and Yoshio Okahata
Journal of the American Chemical Society 2001 123 (44), 11037-11041
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Complexation-Induced Unfolding of Heterocyclic Ureas. Simple Foldamers Equilibrate with Multiply Hydrogen-Bonded Sheetlike Structures¹
Perry S. Corbin, Steven C. Zimmerman, Paul A. Thiessen, Natalie A. Hawryluk, and Thomas J. Murray
Journal of the American Chemical Society 2001 123 (43), 10475-10488
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Crystal Engineering Using Anilic Acids and Dipyridyl Compounds through a New Supramolecular Synthon
Md. Badruz Zaman, Masaaki Tomura, and Yoshiro Yamashita
The Journal of Organic Chemistry 2001 66 (18), 5987-5995
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Polysaccharide−Polynucleotide Complexes. 2. Complementary Polynucleotide Mimic Behavior of the Natural Polysaccharide Schizophyllan in the Macromolecular Complex with Single-Stranded RNA and DNA
Kazuo Sakurai, Masami Mizu, and Seiji Shinkai
Biomacromolecules 2001 2 (3), 641-650
Abstract | Full Text HTML | PDF | PDF w/ Links
Polymorphs of a 1:1 Cocrystal with Tunnel and Layer Structures: p,p‘-Biphenol/Dimethyl Sulfoxide
Shinbyoung Ahn, Benson M. Kariuki, and Kenneth D. M. Harris
Crystal Growth & Design 2001 1 (2), 107-111
Abstract | Full Text HTML | PDF | PDF w/ Links
Theoretical Study of Microscopic Molecular Structure of Helicenebisquinone Aggregates
Hyuk Soon Choi and Kwang S. Kim
The Journal of Physical Chemistry B 2000 104 (47), 11006-11009
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Dissolution Inhibitory Effect of a Urea Additive on a Carboxyl Polymer through a Supramolecular Structure
Yasunari Maekawa, Takao Miwa, Yoshiaki Okabe, Géraldine Rames-Langlade, and Takumi Ueno
Macromolecules 2000 33 (18), 6794-6799
Abstract | Full Text HTML | PDF | PDF w/ Links
Preferential Cocrystallization among Distyrylbenzene Derivatives
Glenn P. Bartholomew, Xianhui Bu, and Guillermo C. Bazan
Chemistry of Materials 2000 12 (8), 2311-2318
Abstract | Full Text HTML | PDF | PDF w/ Links
Applying Polymer Chemistry to Interfaces: Layer-by-Layer and Spontaneous Growth of Covalently Bound Multilayers
P. Kohli and G. J. Blanchard
Langmuir 2000 16 (10), 4655-4661
Abstract | Full Text HTML | PDF | PDF w/ Links
New Hydrogen-Bonded Donor−Acceptor Pairs between Dipyridylacetylenes and 2,5-Dichloro-3,6-dihydroxy-1,4-benzoquinone
Md. Badruz Zaman, Masaaki Tomura, and Yoshiro Yamashita
Organic Letters 2000 2 (3), 273-275
Abstract | Full Text HTML | PDF | PDF w/ Links
Polar Assembly of N,N‘-Bis(4-substituted benzyl)sulfamides
Bing Gong, Chong Zheng, Huaqiang Zeng, and Jin Zhu
Journal of the American Chemical Society 1999 121 (41), 9766-9767
Abstract | Full Text HTML | PDF | PDF w/ Links
Hydrogen-Bonded Self-Assembled Peptide Nanotubes from Cystine-Based Macrocyclic Bisureas
Darshan Ranganathan, C. Lakshmi, and Isabella L. Karle
Journal of the American Chemical Society 1999 121 (26), 6103-6107
Abstract | Full Text HTML | PDF | PDF w/ Links
Predicting Crystalline Packing Arrangements of Molecules That Form Hydrogen-Bonded Tapes
Donovan N. Chin, G. Tayhas R. Palmore, and George M. Whitesides
Journal of the American Chemical Society 1999 121 (10), 2115-2122
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Theoretical Study of Strong Hydrogen Bonds between Neutral Molecules: The Case of Amine Oxides and Phosphine Oxides as Hydrogen Bond Acceptors
Ibon Alkorta and Jose Elguero
The Journal of Physical Chemistry A 1999 103 (2), 272-279
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A Robust Two-Dimensional Hydrogen-Bonded Network: The Sulfamide Moiety as a New Building Block for the Design of Molecular Solids
Bing Gong, Chong Zheng, Ewa Skrzypczak-Jankun, Yinfa Yan, and Jianhua Zhang
Journal of the American Chemical Society 1998 120 (43), 11194-11195
Abstract | Full Text HTML | PDF | PDF w/ Links
Novel Self-Assembly of m-Xylylene Type Dithioureas by Head-to-Tail Hydrogen Bonding
Yoshito Tobe, Shin-ichi Sasaki, Masaaki Mizuno, Keiji Hirose, and Koichiro Naemura
The Journal of Organic Chemistry 1998 63 (21), 7481-7489
Abstract | Full Text HTML | PDF | PDF w/ Links
Self-Assembling Capsules
M. Morgan Conn and Julius Rebek, Jr.
Chemical Reviews 1997 97 (5), 1647-1668
Abstract | Full Text HTML | PDF | PDF w/ Links
Enhanced Carboxylate Binding Using Urea and Amide-Based Receptors with Internal Lewis Acid Coordination: A Cooperative Polarization Effect
Martin Patrick Hughes and Bradley D. Smith
The Journal of Organic Chemistry 1997 62 (13), 4492-4499
Abstract | Full Text HTML | PDF | PDF w/ Links
NMR Studies of the Reversible Dimerization and Guest Exchange Processes of Tetra Urea Calix[4]arenes Using a Derivative with Lower Symmetry
Oliver Mogck, Miquel Pons, Volker Böhmer, and Walter Vogt
Journal of the American Chemical Society 1997 119 (24), 5706-5712
Abstract | Full Text HTML | PDF | PDF w/ Links
Molecular Recognition: The Demonstration of 1,3-Bis[(pyrid-2-ylamino)carbonyl]adamantane as an Exceptionally Versatile Assembler of One-Dimensional Motifs
Isabella L. Karle, Darshan Ranganathan, and V. Haridas
Journal of the American Chemical Society 1997 119 (12), 2777-2783
Abstract | Full Text HTML | PDF | PDF w/ Links
The Indol-2-ylglyoxylamide Moiety: A New Building Block for the Design and Self-Assembly of Hydrogen Bond Networks
David St. C. Black, Donald C. Craig, and Darryl B. McConnell
Journal of the American Chemical Society 1996 118 (34), 8148-8149
Abstract | Full Text HTML | PDF | PDF w/ Links
The Pinched Cone Conformation of Calix[4]arenes: Noncovalent Rigidification of the Calix[4]arene Skeleton
Jurgen Scheerder, Remko H. Vreekamp, Johan F. J. Engbersen, Willem Verboom, John P. M. van Duynhoven, and David N. Reinhoudt
The Journal of Organic Chemistry 1996 61 (10), 3476-3481
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Systematic Crystallographic Investigation of Hydrogen-Bonded Networks Involving Monohydrogen Tartrate−Amine Complexes: Potential Materials for Nonlinear Optics
Renuka Kadirvelraj, Arun M. Umarji, Ward T. Robinson, Santanu Bhattacharya, and Tayur N. Guru Row
Chemistry of Materials 1996 8 (9), 2313-2323
Abstract | Full Text HTML | PDF | PDF w/ Links
Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: increasing enantioselectivity by catalyst dilution
Ho Sik Rho, Sang Ho Oh, Ji Woong Lee, Jin Yong Lee, Jik Chin, Choong Eui Song
Chemical Communications 2008 (10), 1208
Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts
Stephen J. Connon
Chemical Communications 2008 (22), 2499
Amide-water hydrogen-bond motifs in alkali-metal/crown ether complexes of carbamoyldicyanomethanide, C(CONH2)(CN)2−
David R. Turner, Sze Nee Pek, Stuart R. Batten
New Journal of Chemistry 2008 32 (4), 719
Crystal engineering with urea and thiourea hydrogen-bonding groups
Radu Custelcean
Chemical Communications 2008 (3), 295
Homomeric and heteromeric self-assembly of hybrid ureido–imidazole compounds
Yves-Marie Legrand, Mathieu Michau, Arie van der Lee, Mihail Barboiu
CrystEngComm 2008 10 (5), 490
Reinforced Self-Assembly of Hexa-peri-hexabenzocoronenes by Hydrogen Bonds: From Microscopic Aggregates to Macroscopic Fluorescent Organogels
Xi Dou, Wojciech Pisula, Jishan Wu, Graham J. Bodwell, Klaus Müllen
Chemistry - A European Journal 2008 14 (1), 240-249
Edge‐to‐Face CH/π Aromatic Interaction and Molecular Self‐Recognition in <i>epi</i>‐Cinchona‐Based Bifunctional Thiourea Organocatalysis
Gábor Tárkányi, Péter Király, Szilárd Varga, Benedek Vakulya, Tibor Soós
Chemistry - A European Journal 2008, 6078
Heterotapes: A Persistent, Dual-Synthon Hydrogen-Bonding Motif
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Chemistry – An Asian Journal 2007 2 (12), 1534-1539
Succinimidyl Carbamate Derivatives fromN-Protected α-Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids
Lucile Fischer, Vincent Semetey, Jose-Manuel Lozano, Arnaud-Pierre Schaffner, Jean-Paul Briand, Claude Didierjean, Gilles Guichard
European Journal of Organic Chemistry 2007 2007 (15), 2511-2525
Anion Separation with Metal–Organic Frameworks
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European Journal of Inorganic Chemistry 2007 2007 (10), 1321-1340
Designing a Cocrystal of γ-Amino Butyric Acid
Mazal Wenger, Joel Bernstein
Angewandte Chemie International Edition 2006 45 (47), 7966-7969
Designing a Cocrystal of γ-Amino Butyric Acid
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Angewandte Chemie 2006 118 (47), 8134-8137
Cocrystal Formation during Cogrinding and Storage is Mediated by Amorphous Phase
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Pharmaceutical Research 2006 23 (10), 2381-2392
Dual roles of alkyl alcohols as syndiotactic-specificity inducers and accelerators in the radical polymerization ofN-isopropylacrylamide and some properties of syndiotactic poly(N-isopropylacrylamide)
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Journal of Polymer Science Part A: Polymer Chemistry 2006 44 (15), 4450-4460
Organocatalysis Mediated by (Thio)urea Derivatives
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Chemistry - A European Journal 2006 12 (21), 5418-5427
Asymmetrische Katalyse durch chirale Wasserstoffbrückendonoren
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Angewandte Chemie 2006 118 (10), 1550-1573
Asymmetric Catalysis by Chiral Hydrogen-Bond Donors
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Angewandte Chemie International Edition 2006 45 (10), 1520-1543
Pulsed Gradient Spin Echo (PGSE) Diffusion Measurements as a Tool for the Elucidation of a New Type of Hydrogen-Bonded Bicapsular Aggregate
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Chemistry - A European Journal 2006 12 (3), 877-886
Exploring conformationally flexible hydrogen-bond-functionalized ligand and counter anions in metal?organic frameworks of Cu(ii)
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New Journal of Chemistry 2006 30 (9), 1267
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Chirality 2006 18 (9), 762-771
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New Journal of Chemistry 2006 30 (1), 65
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Multicomponent Organic Alloys Based on Organic Layered Crystals
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Enantioselective Thiourea-Catalyzed Acyl-Mannich Reactions of Isoquinolines
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Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes by Using a Simple Thiourea Organocatalyst
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Russian Journal of General Chemistry 2005 75 (10), 1610-1617
1H,13C and19F NMR spectroscopy of polyfluorinated ureas. Correlations involving NMR chemical shifts and electronic substituent effects
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Magnetic Resonance in Chemistry 2005 43 (5), 389-397
Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors
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Organic & Biomolecular Chemistry 2005, 4299
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Chemistry - A European Journal 2005 11 (10), 3097-3104
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Chemical Communications 2005 (37), 4696
Noncovalent Synthesis Using Hydrogen Bonding
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Angewandte Chemie International Edition 2001 40 (13), 2382-2426
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Angewandte Chemie 2001 113 (13), 2446-2492
Gleichzeitig auftretende polymorphe Modifikationen
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Angewandte Chemie 1999 111 (23), 3646-3669
Effizienter intermolekularer Ladungstransport in selbstorganisierten Fasern aus Mono- und Bithiophenen mit zwei Harnstoffeinheiten
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Angewandte Chemie 1999 111 (10), 1486-1490
π-π INTERACTIONS IN SELF-ASSEMBLY
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Journal of Physical Organic Chemistry 1997, 254
Cyclobis(Paraquat-4,4′-Biphenylene)–an Organic Molecular Square
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Angewandte Chemie 1996 108 (12), 1425-1427
Selbstorganisation in natürlichen und in nichtnatürlichen Systemen
Douglas Philp, J. Fraser Stoddart
Angewandte Chemie 1996 108 (11), 1242-1286
Network hydrogen bonding in two new cocrystals sustained by 731-1731-1731-1, a tetrahedral hydrogen bond donor
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Muster aus H-Brücken: ihre Funktionalität und ihre graphentheoretische Analyse in Kristallen
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Angewandte Chemie 1995 107 (15), 1689-1708
X-ray structure of 1,3-adamantane dicarbonamide
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Journal of Chemical Crystallography 1995 25 (1), 11-14
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Rosa M. Claramunt, Julio Dotor, Dionisia Sanz, Concepci�n Foces-Foces, Antonio L. Llamas-Saniz, Jos� Elguero, Robert Flammang, Jean Pierre Morizur, Erik Chapon, Jeanine Tortajada
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Steven J. Geib, Cristina Vicent, Erkang Fan, Andrew D. Hamilton
Angewandte Chemie 1993 105 (1), 83-85
A Self-Assembling, Hydrogen-Bonded Helix
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Angewandte Chemie International Edition in English 1993 32 (1), 119-121
Crystal and molecular structure of two isomeric N-methyl iodides of thiobinupharidine:trans,trans-N,N′-dmethyl-thiobinupharidine diiodide dihydrate acetone solvate andcis,trans-N,N′-dimethylthiobinupharidine diiodide dihydrate methanol solvate
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ChemInform 1991 22 (6), 43-43

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Hydrogen bond-directed cocrystallization and molecular recognition properties of diarylureas

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