Molecules to supermolecules and self assembly : a study of some cocrystals of cyanuric acid

Abstract The preparation and structure elucidation of cocrystals 1a , 1b , 2a – 4a , formed from cyanuric acid ( CA ) and the aza-donor compounds 4,7-phenanthroline, 1,7-phenanthroline, phenazine and 1,3-bis(4-pyridyl)propane, respectively, have been reported. While CA forms different types of self-assembling modes—monomers ( 1a ), dimers ( 1b and 4a ) and infinite tapes ( 2a and 3a )—the recognition of the constituents, however, is through a triple hydrogen-bonding pattern, consisting of an N–H⋯N and two C–H⋯O hydrogen bonds, except in 4a .

[1]  G. Whitesides,et al.  Molecular self-assembly through hydrogen bonding : supramolecular aggregates based on the cyanuric acid.melamine lattice , 1993 .

[2]  J. Atwood,et al.  Structural classification and general principles for the design of spherical molecular hosts. , 1999, Angewandte Chemie.

[3]  J. Neudörfl,et al.  Comparative supramolecular chemistry of coronene, hexahelicene, and [18]crown-6: hydrated and solvated molecular complexes of [18]crown-6 with 5-hydroxyisophthalic acid and related di- and tricarboxylic acids. , 2001, Chemistry.

[4]  L. MacGillivray,et al.  An inverted metal-organic framework with compartmentalized cavities constructed by using an organic bridging unit derived from the solid state. , 2002, Angewandte Chemie.

[5]  Giannis S. Papaefstathiou and,et al.  An Inverted Metal-Organic Framework with Compartmentalized Cavities Constructed by Using an Organic Bridging Unit Derived from the Solid State , 2002 .

[6]  A. Gavezzotti,et al.  Molecular recognition in organic crystals: directed intermolecular bonds or nonlocalized bonding? , 2005, Angewandte Chemie.

[7]  V. Pedireddi,et al.  Replacing the hydrogen in the intermolecular hydrogen bond of the cyanuric acid-bipyridyl adduct by Ag(I) , 2000 .

[8]  G. Whitesides,et al.  Synthesis and Evaluation of Thioether-Based Tris-Melamines as Components of Self-Assembled Aggregates Based on the CA.M Lattice. , 1996, The Journal of organic chemistry.

[9]  Susumu Kitagawa,et al.  Functional porous coordination polymers. , 2004, Angewandte Chemie.

[10]  G. Desiraju,et al.  Engineering of an octupolar non-linear optical crystal: tribenzyl isocyanurate , 1997 .

[11]  G. Whitesides,et al.  Solid-State Structures of Hydrogen-Bonded Tapes Based on Cyclic Secondary Diamides , 1994 .

[12]  M. Filigenzi,et al.  Assessment of Melamine and Cyanuric Acid Toxicity in Cats , 2007, Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc.

[13]  T. Row,et al.  Three-dimensional supramolecular H-bonding network in the compounds containing hexamethylenetetramine and aquated Ni(II) or Cd(II) salts , 2007 .

[14]  V. Pedireddi,et al.  Investigation of some layered structures of cyanuric acid , 2002 .

[15]  Benjamin M. Scott,et al.  Balancing supramolecular reagents for reliable formation of co-crystals. , 2006, Chemical communications.

[16]  B. Sarma,et al.  Tetrakis(4-sulfophenyl)methane dodecahydrate. Reversible and selective water inclusion and release in an organic host , 2007 .

[17]  O. Fabelo,et al.  Hydrogen Bond-Directed Frameworks Based on 1,2,4,5-Benzene-Tetracarboxylate , 2005 .

[18]  H Li,et al.  Modular chemistry: secondary building units as a basis for the design of highly porous and robust metal-organic carboxylate frameworks. , 2001, Accounts of chemical research.

[19]  C. Aakeröy,et al.  Supramolecular reagents: versatile tools for non-covalent synthesis. , 2005, Chemical communications.

[20]  C. Rao,et al.  Sensitive dependence of the hydrogen-bonded assemblies in cyanuric acid–4,4′-bipyridyl adducts on the solvent and the structure of the parent acid , 2000 .

[21]  G. Desiraju,et al.  Packing modes in some mono- and disubstituted phenylpropiolic acids: repeated occurrence of the rare syn,anti catemer. , 2006, Chemistry, an Asian journal.

[22]  V. Pedireddi,et al.  Novel Supramolecular Assemblies of Coordination Polymers of Zn(II) and Bis(4-nitrophenyl)phosphoric Acid with Some Aza-Donor Compounds , 2007 .

[23]  J. Wuest,et al.  Engineering hydrogen-bonded molecular crystals built from derivatives of hexaphenylbenzene and related compounds. , 2007, Journal of the American Chemical Society.

[24]  George M. Whitesides,et al.  Design and synthesis of hydrogen-bonded aggregates. Theory and computation applied to three systems based on the cyanuric acid-melamine lattice , 1995 .

[25]  G. Whitesides,et al.  Self-assembly based on the cyanuric acid-melamine lattice , 1990 .

[26]  K. Harris Fundamental and Applied Aspects of Urea and Thiourea Inclusion Compounds , 2007 .

[27]  A. J. Blake,et al.  Polymorphism in hydrogen bonded frameworks; cyanuric acid–bis(4-pyridyl)ethene adducts , 2003 .

[28]  K. Arora,et al.  A rational study of crystal engineering of supramolecular assemblies of 1,2,4,5-benzenetetracarboxylic acid. , 2003, The Journal of organic chemistry.

[29]  L. Falvello,et al.  CHARACTERIZATION OF THE ISOCYANURATE COMPLEXES M(CYAN-N)-(H2O)5(CYAN-N).2H2O (M=NI, CO, MN) COMPOUNDS THAT FORM MOLECULAR RIBBONS IN THE SOLID STATE , 1995 .

[30]  C. Rao,et al.  An organic channel structure formed by the supramolecular assembly of trithiocyanuric acid and 4,4′-bipyridyl , 1999 .

[31]  G. Whitesides,et al.  Design of Organic Structures in the Solid State: Molecular Tapes Based on the Network of Hydrogen Bonds Present in the Cyanuric Acid.cntdot.Melamine Complex , 1994 .

[32]  E. Suresh,et al.  Nucleobases in molecular recognition: molecular adducts of adenine and cytosine with COOH functional groups. , 2005, Angewandte Chemie.

[33]  Jean-Marie Lehn,et al.  Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices (Nobel Lecture) , 1988 .

[34]  G. Desiraju,et al.  Crystal structure prediction of aminols: advantages of a supramolecular synthon approach with experimental structures. , 2005, Journal of the American Chemical Society.

[35]  Scott R. Wilson,et al.  Self-Assembly of 1,3,5-Benzenetricarboxylic Acids (Trimesic Acids) and Several Analogues in the Solid State† , 1996 .

[36]  L. Falvello,et al.  The Cyanurate Ribbon in Structural Coordination Chemistry: An Aggregate Structure That Persists across Different Coordination Environments and Structural Types , 1997 .

[37]  M. Zaworotko,et al.  Exciplex fluorescence as a diagnostic probe of structure in coordination polymers of Zn2+ and 4,4'-bipyridine containing intercalated pyrene and enclathrated aromatic solvent guests. , 2007, Journal of the American Chemical Society.

[38]  Gautam R. Desiraju,et al.  The Weak Hydrogen Bond: In Structural Chemistry and Biology , 1999 .

[39]  S. Varughese,et al.  A competitive molecular recognition study: syntheses and analysis of supramolecular assemblies of 3,5-dihydroxybenzoic acid and its bromo derivative with some N-donor compounds. , 2006, Chemistry.

[40]  K. Biradha,et al.  Multicomponent assembly of a pyrazine-pillared coordination cage that selectively binds planar guests by intercalation. , 2003, Angewandte Chemie.

[41]  C. Rao,et al.  Hydrothermal synthesis of organic channel structures: 1:1 hydrogen-bonded adducts of melamine with cyanuric and trithiocyanuric acids , 1999 .

[42]  M. Zaworotko,et al.  18-Fold Interpenetration and Concomitant Polymorphism in the 2:3 Co-Crystal of Trimesic Acid and 1,2-Bis(4-pyridyl)ethane† , 2005 .

[43]  Scott R. Wilson,et al.  SELF-ASSEMBLY OF 1,3,5-BENZENETRICARBOXYLIC (TRIMESIC) ACID AND ITS ANALOGUES , 1999 .

[44]  W. Jones,et al.  Co-crystal structures of 4,7-phenanthroline and carboxylic acids: synthon competition and prediction , 2002 .

[45]  Jerry March,et al.  Advanced Organic Chemistry: Reactions, Mechanisms, and Structure , 1977 .

[46]  K. Harris,et al.  Structural rationalisation of co-crystals formed between trithiocyanuric acid and molecules containing hydrogen bonding functionality. , 2005, Chemistry.

[47]  G. Whitesides,et al.  Solid-state structures of rosette and crinkled tape motifs derived from the cyanuric acid melamine lattice , 1992 .

[48]  M. Du,et al.  Cocrystallization of Trimesic Acid and Pyromellitic Acid with Bent Dipyridines , 2005 .

[49]  W. Jones,et al.  Identification of supramolecular templates: design of solid-state photoreactivity using structural similarity , 2003 .

[50]  R. E. Marsh,et al.  The crystal structure of trimesic acid (benzene-1,3,5-tricarboxylic acid) , 1969 .

[51]  M. Jennings,et al.  Crystal packing in tetraphenylphosphonium salts of trithiocyanuric acid and its methanol solvate , 2004 .