Phosphonoacetic acid as a building block in supramolecular chemistry: salts with organic polyamines

2003 ◽  
Vol 59 (1) ◽  
pp. 87-99 ◽  
Author(s):  
Katharine F. Bowes ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Choudhury M. Zakaria ◽  
Christopher Glidewell
Keyword(s):  
Supramolecular Chemistry ◽  
Building Block ◽  
Three Dimensional ◽  
Neutral Molecule ◽  
Two Dimensional ◽  
Phosphonoacetic Acid ◽  
Acid Component ◽  
A Chain

Phosphonoacetic acid, (HO)2P(O)CH2COOH, forms adducts with a range of amines. The acid component in these adducts may be the neutral molecule C2H5O5P, the mono-anion (C2H4O5P)− or the di-anion (C2H3O5P)2−. The substructure formed by the acid component takes the form of simple chains in compounds (1)–(3), which are the 1:1 adducts formed with 1,4-diazabicyclo[2.2.2]octane, 4,4′-bipyridyl and 1,3-trimethylenedipiperidine, respectively. These adducts contain C2H5O5P, (C2H4O5P)− and (C2H3O5P)2−, respectively, although (3) is solvated by a mixture of methanol and water. The (C2H4O5P)− anion substructure in (4), which is the adduct formed with meso-5,5,7,12,12,14-hexa-C-methyl-1,4,8,11-tetraazacyclotetradecane, is a chain of spiro-fused rings, while the substructure in (5), which is the adduct formed with 2,2′-dipyridylamine, is a chain of edge-fused rings. In (6), the adduct formed with 1,2-bis(4′-pyridyl)ethane, the anion substructure is two-dimensional. The chain substructures are linked by the amine units into two-dimensional structures in (1) and (4) and into three-dimensional frameworks in (2), (3) and (5), while the anion sheets in (6) are likewise linked by the amine units into a three-dimensional framework.

(1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines

2003 ◽  
Vol 59 (1) ◽  
pp. 118-131 ◽  
Author(s):  
Choudhury M. Zakaria ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Dicarboxylic Acid ◽  
Supramolecular Chemistry ◽  
Building Block ◽  
Three Dimensional ◽  
Neutral Molecule ◽  
Acid Component ◽  
Camphoric Acid

(1R,3S)-Camphoric acid [(1R,3S)-1,2,2,-trimethylcyclopentane-1,3-dicarboxylic acid, C10H16O4] forms adducts with a range of amines in which the acid component may be the neutral molecule, the mono-anion (C10H15O4)− or the di-anion (C10H14O4)2−. The structures generated by the hard hydrogen bonds take the form of chains in the 1:1 adducts (II) and (III) formed with 4,4′-bipyridyl and 1,2-bis(4-pyridyl)ethane. There are single sheets in the hydrated 1:1 adduct (IV) formed with 1,4-diazabicyclo[2.2.2]octane, and pairwise-interwoven sheets in the 2:1 adduct (V) formed with hexamethylenetetramine. Three-dimensional frameworks are present in the salt-like 1:1 adduct (VI) formed with piperazine and in the hydrated 3:1 adduct (VII) formed with N,N′-dimethylpiperazine. This latter adduct contains both neutral C10H16O4 and anionic (C10H15O4)− units. In (II), (III) and (IV), the chain and sheet substructures are linked by C—H...O hydrogen bonds to form three-dimensional frameworks. The monoclinic polymorph of camphoric acid itself (I) has been reinvestigated.

Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines

2003 ◽  
Vol 59 (2) ◽  
pp. 248-262 ◽  
Author(s):  
Katharine F. Bowes ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Water Molecules ◽  
Two Dimensional ◽  
Phosphonoacetic Acid ◽  
Space Group ◽  
Hydrated Salt ◽  
Hydrogen Bonded

The structures of seven salts formed by phosphonopropionic acid with organic diamines are reported; in these salts, the hydrogen-bonded substructures formed by the anions can be zero-, one- or two-dimensional, while the overall hydrogen-bonded supramolecular structures are three-dimensional. The 1:1 adduct, compound (1), formed between 1,2-bis(4′-pyridyl)ethene and phosphonopropionic acid is a salt, [{(C12H10N2)H2}2+]·[(C12H10N2)]·[(C3H6O5P)−]2, in which both diamine components lie across centres of inversion in space group P21/c. The anions form hydrogen-bonded head-to-head dimers, and these are linked by the two diamine units into sheets, which are themselves linked by C—H...O hydrogen bonds. With 2,2′-dipyridylamine the acid forms the hydrated salt [{(C10H9N3)H}+]·[(C3H6O5P)−]·H2O (2), in which all components are disordered with occupancy 0.5 in space group Fmm2. The anions form head-to-tail dimers, which are linked into sheets by the cations, and the sheets are linked into a three-dimensional framework by the water molecules. The piperazine salt [{(C4H10N2)H2}2+]·[(C3H5O5P)2−] (3) contains simple anion chains linked into a three-dimensional framework by the two independent cations, both of which are centrosymmetric. In the hydrated salt formed by N,N′-dimethylpiperazine, [{(MeNC4H8NMe)H2}2+]·[(C3H6O5P)−]2·(H2O)2 (4), head-to-tail anion chains combine with the water molecules to form a three-dimensional framework, which encloses voids that contain the cations. In the 4,4′-bipyridyl adduct [{(C10H8N2)H0.72}0.72+]·[{(H0.5O)3PCH2CH2COOH0.78}0.72−] (5), there is extensive disorder of the H atoms that are bonded to N and O atoms, and the anion chains are linked by the cations into sheets, which are themselves linked by C—H...O hydrogen bonds. In the 1:2 adduct formed with 1,2-bis(4′-pyridyl)ethane, [{(C12H12N2)H2}2+]·[(C3H6O5P)−]2 (6), where the cation lies across an inversion centre, the anions form molecular ladders. These ladders are linked into sheets by the cations, which are themselves linked by C—H...O hydrogen bonds. In the methanol-solvated salt formed with 2,6-dimethylpiperazine, [{(C6H14N2)H2}2+]·[(C3H6O5P)−]2· (CH4O)0.34 (7), the anions form sheets that are linked into a three-dimensional framework by the cations. The supramolecular structures are compared with those of analogous salts formed by phosphonoacetic acid.

Supramolecular chemistry of amine–phenol adducts; novel three-dimensional framework structures in adducts of bis(2-aminoethyl)amine with 4,4′-sulfonyldiphenol, 1,1,1-tris(4-hydroxyphenyl)ethane and 3,5-dihydroxybenzoic acid, and in the methanol-solvated adduct of tris(2-aminoethyl)amine with 4,4′-biphenol

2000 ◽  
Vol 56 (1) ◽  
pp. 68-84 ◽  
Author(s):  
Christopher Glidewell ◽  
George Ferguson ◽  
Richard M. Gregson ◽  
Charles F. Campana
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Three Dimensional ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Dihydroxybenzoic Acid ◽  
Nearest Neighbours ◽  
Molecular Components

Bis(2-aminoethyl)amine–4,4′-sulfonyldiphenol (1/3) (1) (orthorhombic Pccn with Z′ = 0.5) is a salt, [HN(CH2CH2NH3)2]2+.[O2S(C6H4O)2]2−.[O2S(C6H4OH)2]2, containing both dianionic and neutral bis-phenol units. The neutral and anionic bis-phenol units are linked by strong O—H...O− hydrogen bonds to form ladders built from R{_4}{^4}(48) rings: each ladder is interwoven with its two nearest neighbours to form a continuous two-dimensional sheet. The amine cations play two roles: they link each ladder to its two next-nearest neighbours by means of N—H...O hydrogen bonds and they also link each sheet to the two neighbouring sheets, again via N—H...O hydrogen bonds, thus generating a three-dimensional framework. Bis(2-aminoethyl)amine–1,1,1-tris(4-hydroxyphenyl)ethane–methanol (1/4/1) (2) (triclinic P1¯ with Z′ = 0.5) consists entirely of neutral fragments. The tris-phenol units are linked by O—H...O hydrogen bonds into molecular ladders built from R{_4}{^4}(48) rings: these ladders are linked by the amine units, firstly into sheets and thence into a three-dimensional framework. Bis(2-aminoethyl)amine–3,5-dihydroxybenzoic acid (1/2) (3) (monoclinic P21/c with Z′ = 1) is a salt [HN(CH2CH2NH3)2]2+.[{(HO)2C6H3COO}−]2. The 3,5-dihydroxybenzoate anions are linked by O—H...O hydrogen bonds into interwoven and cross-connected (001) sheets linked by further O—H...O hydrogen bonds into a three-dimensional framework. The (001) sheets are further linked by ladders formed from both cations and anions. Tris(2-aminoethyl)amine–4,4′-biphenol–methanol (1/3/1), (4) (monoclinic P21), is a salt [{(H2NCH2CH2)2N(CH2CH2NH3)}+]2.[OC6H4C6H4O]2−.[HOC6H4C6H4OH]5.[MeOH]2, with Z′ = 1. The asymmetric unit, containing ten independent molecular components, can be regarded as a supermolecule held together by a total of 13 independent hydrogen bonds, of O—H...O, O—H...N and N—H...O types. The supermolecules are linked by O—H...O and N—H...O hydrogen bonds into two-dimensional sheets, generated by translation; further N—H...O hydrogen bonds around the 21 screw axes link neighbouring sheets together into a three-dimensional framework.

Oligosiloxanediols as building blocks for supramolecular chemistry: hydrogen-bonded adducts with amines form supramolecular structures in zero, one and two dimensions

2000 ◽  
Vol 56 (2) ◽  
pp. 273-286 ◽  
Author(s):  
Brian O'Leary ◽  
Trevor R. Spalding ◽  
George Ferguson ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Building Blocks ◽  
Two Dimensions ◽  
Supramolecular Structures ◽  
Structural Motif ◽  
Two Dimensional ◽  
The Third ◽  
A Chain ◽  
Hydrogen Bonded

The structure of 1,1,3,3,5,5-hexaphenyltrisiloxane-1,5-diol–pyrazine (4/1), (C36H32O4Si3)4·C4H4N2 (1), contains finite centrosymmetric aggregates; the diol units form dimers, by means of O—H...O hydrogen bonds, and pairs of such dimers are linked to the pyrazine by means of O—H...N hydrogen bonds. In 1,1,3,3,5,5-hexaphenyltrisiloxane-1,5-diol–pyridine (2/3), (C36H32O4Si3)2·(C5H5N)3 (2), the diol units are linked into centrosymmetric pairs by means of disordered O—H...O hydrogen bonds: two of the three pyridine molecules are linked to the diol dimer by means of ordered O—H...N hydrogen bonds, while the third pyridine unit, which is disordered across a centre of inversion, links the diol dimers into a C 3 3(9) chain by means of O—H...N and C—H...O hydrogen bonds. In 1,1,3,3-tetraphenyldisiloxane-1,3-diol–hexamethylenetetramine (1/1), (C24H22O3Si2)·C6H12N4 (3), the diol acts as a double donor and the hexamethylenetetramine acts as a double acceptor in ordered O—H...N hydrogen bonds and the structure consists of C 2 2(10) chains of alternating diol and amine units. In 1,1,3,3-tetraphenyldisiloxane-1,3-diol–2,2′-bipyridyl (1/1), C24H22O3Si2·C10H8N2 (4), there are two independent diol molecules, both lying across centres of inversion and therefore both containing linear Si—O—Si groups: each diol acts as a double donor of hydrogen bonds and the unique 2,2′-bipyridyl molecule acts as a double acceptor, thus forming C 2 2(11) chains of alternating diol and amine units. The structural motif in 1,1,3,3-tetraphenyldisiloxane-1,3-diol–pyrazine (2/1), (C24H22O3Si2)2·C4H4N2 (5), is a chain-of-rings: pairs of diol molecules are linked by O—H...O hydrogen bonds into centrosymmetric R 2 2(12) dimers and these dimers are linked into C 2 2(13) chains by means of O—H...N hydrogen bonds to the pyrazine units. 1,1,3,3-Tetraphenyldisiloxane-1,3-diol–pyridine (1/1), C24H22O3Si2·C5H5N (6), and 1,1,3,3-tetraphenyldisiloxane-1,3-diol–pyrimidine (1/1), C24H22O3Si2·C4H4N2 (7), are isomorphous: in each compound the amine unit is disordered across a centre of inversion. The diol molecules form C(6) chains, by means of disordered O—H...O hydrogen bonds, and these chains are linked into two-dimensional nets built from R 6 6(26) rings, by a combination of O—H...N and C—H...O hydrogen bonds.

scholarly journals Poly[(μ3-5-hydroxyisophthalato)[μ2-1,1′-(1,4-phenylene)bis(1H-imidazole)]copper]

IUCrData ◽  
2016 ◽  
Vol 1 (11) ◽  
Author(s):  
Hong-Hong Tao ◽  
Yu-Han Chen ◽  
Ya-Sai Liu ◽  
Zhuo-Ga Deji
Keyword(s):  
Three Dimensional ◽  
Dimensional Structure ◽  
Supramolecular Network ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Bridging Ligands ◽  
Trigonal Bipyramidal ◽  
A Chain ◽  
Organic Linker ◽  
Distorted Trigonal Bipyramidal

The title compound, [Cu(C8H4O5)(C12H10N4)]n, was obtained by the reaction of copper(II) nitrate hydrate, with the OH-BDC organic linker and bib molecules [OH-BDC = 5-hydroxyisophthalic acid and bib = 1,4-bis(imidazol-1-yl)benzene]. The asymmetric unit comprises one CuIIcation, one OH-BDC−2dianion and a bib ligand. The CuIIion is coordinated by three carboxylate O atoms and two bib-N atoms, all from bridging ligands, to form a slightly distorted trigonal–bipyramidal geometry. The CuIIions are bridged by OH-BDC−2ligands, forming a chain along the [100] direction; the chains are connected by bib molecules to form a two-dimensional net. In topological terms, considering the CuIIatoms as nodes and the OH-BDC−2ligands as linkers, the two-dimensional structure can be simplified as a typical 2-nodal 3,5 L2 plane network. The crystal structure features O—H...O hydrogen bonds between OH-BDC−2anions, resulting in a three-dimensional supramolecular network.

[1-(Pyrazin-2-yl)ethylidene]hydrazine: a new multitopic ligand for the design of hybrid molecular frameworks

2018 ◽  
Vol 74 (4) ◽  
pp. 424-427
Author(s):  
Muhammad Arif Kassim ◽  
Ubaidullah H. M. Yassin ◽  
Ai Ling Tan ◽  
Anwar Usman ◽  
Malai Haniti S. A. Hamid
Keyword(s):  
Double Bond ◽  
Solid State ◽  
Supramolecular Chemistry ◽  
Title Compound ◽  
Antimicrobial Agents ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Two Dimensional ◽  
Compound C ◽  
Dimensional Network

Hydrazones and their derivatives are closely related to imine compounds and are potential antimicrobial agents. They have also found application in supramolecular chemistry as multitopic ligands to link multiple metal centres for the design of hybrid molecular frameworks. The molecule of the title compound, C6H8N4, consists of an imine linkage with an N—N bond length of 1.3540 (14) Å. This asymmetric compound is nearly planar and adopts an E configuration about the azomethine C=N double bond. In the solid state, there are two intermolecular N—H...N interactions that interconnect the molecules into a two-dimensional network. The three-dimensional arrangement of the crystal packing is further stabilized by intermolecular π–π interactions interconnecting the centroids of the heterocyclic rings.

scholarly journals Supramolecular tessellations by the exo-wall interactions of pagoda[4]arene

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xiao-Ni Han ◽  
Ying Han ◽  
Chuan-Feng Chen
Keyword(s):  
Charge Transfer ◽  
Supramolecular Chemistry ◽  
Building Block ◽  
Two Dimensional ◽  
Potential Applications ◽  
New Perspective ◽  
Rhombic Tiling ◽  
Tiling Patterns ◽  
Wall Charge ◽  
Wall Interactions

AbstractSupramolecular tessellation has gained increasing interest in supramolecular chemistry for its structural aesthetics and potential applications in optics, magnetics and catalysis. In this work, a new kind of supramolecular tessellations (STs) have been fabricated by the exo-wall interactions of pagoda[4]arene (P4). ST with rhombic tiling pattern was first constructed by P4 itself through favorable π···π interactions between anthracene units of adjacent P4. Notably, various highly ordered STs with different tiling patterns have been fabricated based on exo-wall charge transfer interactions between electron-rich P4 and electron-deficient guests including 1,4-dinitrobenzene, terephthalonitrile and tetrafluoroterephthalonitrile. Interestingly, solvent modulation and guest selection played a crucial role in controlling the molecular arrangements in the co-crystal superstructures. This work not only proves that P4 is an excellent macrocyclic building block for the fabrication of various STs, but also provides a new perspective and opportunity for the design and construction of supramolecular two-dimensional organic materials.

scholarly journals One-, Two-, and Three-Dimensional Supramolecular Assemblies Based on Tubular and Regular Polygonal Structures of Pillar[n]arenes

CCS Chemistry ◽  
2019 ◽  
pp. 50-63 ◽  
Author(s):  
Shixin Fa ◽  
Takahiro Kakuta ◽  
Tada-aki Yamagishi ◽  
Tomoki Ogoshi
Keyword(s):  
Surface Modification ◽  
Supramolecular Chemistry ◽  
Three Dimensional ◽  
Supramolecular Assemblies ◽  
Two Dimensional ◽  
Macrocyclic Compounds ◽  
Tubular Structures ◽  
One Dimensional ◽  
Symmetrical Shape

Pillar[ n]arenes, which were first reported by our group in 2008, are promising macrocyclic compounds in supramolecular chemistry. The simple, tubular, and highly symmetrical shape of pillar[ n]arenes has allowed various supramolecular assemblies with well-defined structures to be constructed. The pillar-shaped structures of pillar[ n]arenes are suitable for surface modification and formation of one-dimensional (1D) channels. The regular polygonal prism shape of organized pillar[ n]arenes contributes to the construction of highly assembled structures such as two-dimensional (2D) sheets and three-dimensional (3D) spheres. In this minireview, we describe supramolecular assemblies with various dimensions. First, we discuss 1D supramolecular assemblies based on tubular structures of pillar[ n]arenes. Second, 2D supramolecular sheet formation based on regular polygonal structures is described. Finally, 3D supramolecular assemblies such as vesicles and 3D frameworks constructed from pillar[ n]arenes are discussed.

3,6,9,16,19,22-Hexaazatricyclo[22.2.2.211,14]triconta-1(26),11(29),12,14(30),24,27-hexaene, C24H38N6, as a building block in supramolecular chemistry: structures in two and three dimensions

2000 ◽  
Vol 56 (2) ◽  
pp. 287-298 ◽  
Author(s):  
Christopher Glidewell ◽  
George Ferguson ◽  
Richard M. Gregson ◽  
Alan J. Lough
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Building Block ◽  
Three Dimensional ◽  
Three Dimensions ◽  
Single Type ◽  
Water Molecules ◽  
Minor Components ◽  
Cation Site ◽  
Cation Sites

The adduct (1) formed between the hexaaza macrocycle 3,6,9,16,19,22-hexaazatricyclo[22.2.2.211,14]triconta-1(26),11(29),12,14(30),24,27-hexaene, C24H38N6, and 4,4′-sulfonyldiphenol, O2S(C6H4OH)2, is a salt [(C24H40N6)2+]·2[(HOC6H4SO2C6H4O)−], and the adduct (2) formed by the same macrocyclic amine with 4,4′-biphenol is an aquated salt which also contains neutral biphenol molecules, [(C24H40N6)2+]·2[(HOC6H4C6H4O)−]·(HOC6H4C6H4OH).2H2O. In both compounds the cations lie across centres of inversion: there are two crystallographically distinct cation sites in (1) and the conformations of the cations occupying them are quite different. In (2) the single type of cation site is occupied by a conformationally disordered cation: the major and minor components represent two further distinct conformers. In (1) the anions are linked by O—H...O hydrogen bonds into chains, and each cation is linked by a total of six N—H...O hydrogen bonds to anions in four different chains, so linking the chains into continuous sheets. In (2) the anions and the water molecules are linked into sheets, which are further linked into a continuous three-dimensional framework by both the cations and the neutral biphenol units.

Preliminary estimates of the amount of continuous horizontal shortening across an Archean greenstone belt

1985 ◽  
Vol 22 (4) ◽  
pp. 506-513 ◽  
Author(s):  
W. M. Schwerdtner
Keyword(s):  
Greenstone Belt ◽  
Longitudinal Strain ◽  
Three Dimensional ◽  
Two Dimensional ◽  
Strain Measurements ◽  
Northwestern Ontario ◽  
Apparent Variation ◽  
Archean Greenstone Belt ◽  
A Chain ◽  
Line Elements

Simple two-dimensional techniques are used to make an estimate of the total shortening across a narrow greenstone belt in northwestern Ontario. The techniques are based on the basic principle of restoring the predeformational geometry of a horizontal traverse across the belt. Depending on the technique used this traverse is a string of line elements or a chain of finite elements. The strain ratios available for the restoration are minimal values and need to be increased significantly to obtain realistic results. Depending on the strain values selected for the restoration, amounts of horizontal shortening range from 17 to 49%. The actual amount remains unknown, but is thought to be < 50%.In view of the apparent variation in longitudinal strain along the greenstone belt, a three-dimensional treatment seems to be necessary. This would require that strain measurements be taken systematically throughout, rather than along a single traverse across, a greenstone belt segment.

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