Hydrogen-bonded porous solid derived from trimesic amide

Palmans, Anja R. A.; Vekemans, Jef A. J. M.; Kooijman, Huub; Spek, A. L.; Meijer, E. W.

doi:10.1039/a705339h

Cited by 77 publications

(67 citation statements)

References 15 publications

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“…This generates an ideal self-complementary building block to be held by N-H-O and N-H-N hydrogen bonds. This supramolecular structure differs from that of Lightfoot et al [10] and of Palmans et al [12] The unit cell contains two amide and four methanol solvent molecules. Pairs of amide molecules related by an inversion centre are connected into dimers via two N-H/O carbonyl and two N-H/N pyridyl intermolecular hydrogen bonds.…”

Section: Resultscontrasting

confidence: 44%

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An alternating chain of spider-like tris(peptides) stabilized by stacking and by N–H⋯N and N–H⋯OC hydrogen bonding

Kannappan

Tooke

Spek

et al. 2005

Journal of Molecular Structure

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The X-ray crystal structure of the novel spider-like trispeptide N,N 0 ,N 00 -tris(2-aminopyridine)benzene-1,3,5-tricarboxamide shows the unexpected formation of a new extended polymeric architecture. The structure is characterized by cooperative hydrogen bonding generating neighbouring pairs by self-assembly, and stacking between rings. Pairs of amide groups related by an inversion centre are connected into dimers via two N-H/O carbonyl and two N-H/N pyridyl intermolecular hydrogen bonds. The offset-stacked layers are tightly inter-linked (spacing of 3.477 Å ) by hydrogen bonding and aromatic p-p stacking interactions. These dimers are further linked into polymeric chains by hydrogen bonding through bridging methanol solvent molecules. The central aromatic rings of molecules in adjacent dimers are once again related by inversion symmetry, with a perpendicular separation of 3.619 Å .

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Section: Resultscontrasting

confidence: 44%

“…Only three reports of structures are known in which an aromatic ring has been used as the scaffold for three peptide strands [10][11][12]. In these and other related structures the aromatic rings typically adopt one of several known conformations, of which the most common are edge-face, offset stacked and face-face stacked [13,14].…”

Section: Introductionmentioning

confidence: 99%

An alternating chain of spider-like tris(peptides) stabilized by stacking and by N–H⋯N and N–H⋯OC hydrogen bonding

Kannappan

Tooke

Spek

et al. 2005

Journal of Molecular Structure

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“…During the past decade, the design and construction of coordination polymers have attracted much attention because of their intriguing structural topologies and various potential applications, including catalysis, nonlinear optics, sensors, magnetism and molecular recognition [1][2][3][4][5][6][7]. It is well known that organic ligands play crucial roles in the design and construction of desirable frameworks.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of monoaqua(5-bromoisophthalato)(2,2'-bipyridine)- cobalt(II) semihydrate, Co(H₂O)(C₈H₃BrO₄)(C₁₀H₈N₂) · 0.5H₂O

Li¹

2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialAm ixture of 5-bromoisophthalate (Br-ip, 0.1 mmol), 2,2-bipyridine (bipy, 0.1 mmol), Co(OAc)2 · 4H2O(0.1 mmol), KOH (0.10 mmol) and H 2O(15 mL) was placed in aTeflon-lined stainless steel vessel, heated to 160°Cfor 3days, and then cooled to room temperature over 24 h. Red block-shaped crystals were obtained. Elemental analysis -found: C, 44.51 %; H, 2.86 %; N, 5.70 %; calculated for C 18H14CoN2O5.5:C ,44.56 %; H, 2.91 %; N, 5.77 %. Experimental detailsThe Hatoms of the water molecule were not localized. DiscussionDuring the past decade, the design and construction of coordination polymers have attracted much attention because of their intriguing structural topologies and various potential applications, including catalysis, nonlinear optics, sensors, magnetism and molecular recognition [1][2][3][4][5][6][7]. It is well known that organic ligands play crucial roles in the design and construction of desirable frameworks. In this context, benzenedicarboxylic acid and their derivatives (such as 1,3-benzenedicarboxylic acid, 1,4-benzenedicarboxylic acid,5 -hydroxyisophthalic acid and so on) are widely used as building blocks to link metalions and produce interesting metal-organic framework structures. Aseries of metalorganic frameworks with bridging carboxylate ligands and phenanthroline-like terminal chelating ligands have been described recently.The symmetry independent unit of the title structure consists of one cobalt(II) cation, one bridged Br-ip, one bipy, one coordinating water molecule and half free lattice water molecule. The coordination environment around the Co(II) ion can be described as a slightly distorted octahedral. Each Co(II) ion is six-coordinated by two Natoms from one bipy, two chelated carboxylate Oatoms of one Br-ip and one carboxylate Oatom from another Br-ip anion as well as one coordinated water molecule. The Co-Obond lengths are in the range of 2.030(2) -2.398(2) Å and the Co-N bond distances are 2.109(2) and 2.111(2) Å,respectively. In addition, two carboxylate groups of the Br-ip anion exhibit two kinds of coordination modes: one uses the bridging mode connecting two cobalt centers while the other exhibits chelating mode to one cobalt center. The cobalt atoms are bridged by the Br-ip anions along [100] to generate a1Dchains. Bipy molecules are decorating in the chain.

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“…On the other hand, the main strategies used in the field of crystal engineering are basically on the use of either conventional coordinative bonds or weak interactions. Among the non-covalent interactions, hydrogen bonding interactions play important role in designing superstructures and have attracted much interest due to their relative strength and directionality [11][12]. 3-(Sulfonyl-glycine)benzoic acid can act not only as hydrogen bond acceptors but also as hydrogen bond donors, which make it a wonderful candidate for the construction of supramolecular networks.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of triaqua-cis-bis((2-carboxybenzene)sulfonylglycinato) zinc(II), Zn(H2O)3(C9H8NO6S)2

Ma¹,

Wu²,

Lu³

2007

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe mixture of ZnCl2 · 2H2O (1 mmol) and 3-(sulfonyl-glycine)-benzoic acid (2 mmol) was stirred into 15 mL aqueous solution at room temperature. Then the pH was adjusted to approximately 7 with 1 M KOH solution. And then 5 mL ethanol solution of 4,4¢-bipyridine (1 mmol) was added. The reaction mixture was then heated on a water bath for 6 h at 70°C, and then filtered. Colorless crystal were obtained from the mother liquor by slow evaporation at room temperature after 6 weeks. Experimental detailsAll hydrogen atoms were first found in the difference electron density maps, and then placed in the calculated positions. The hydrogen atoms of carboxylate group and water molecules were found from Fourier difference maps and refined freely. The remaining H atoms were refined by riding model with Ueq(H) = 1.2Ueq(C). DiscussionCrystal engineering of metal-organic frameworks (MOFs) is realizable by the choice of metals and the numerous choice and design of ligands, which bears the weight of prospective applications in new chemical separation, ion exchange, and gas adsorption [1][2][3][4][5][6]. In particular, carboxylate ligands have been frequently employed in the construction of microporous inorganic/organic hybrid materials for gas storage purposes. In this context, benzenedicarboxylic acid and their derivatives (such as 1,3-benzenedicarboxylic acid, 1,4-benzenedicarboxylic acid or 5-hydroxyisophtalic acid) are widely used as building blocks to link metal ions to produce interesting metal-organic framework structures and properties [7][8][9][10]. However, much fewer studies on coordination chemistry of flexible carboxylate-containing ligands have been carried out. On the other hand, the main strategies used in the field of crystal engineering are basically on the use of either conventional coordinative bonds or weak interactions. Among the non-covalent interactions, hydrogen bonding interactions play important role in designing superstructures and have attracted much interest due to their relative strength and directionality [11][12]. 3-(Sulfonyl-glycine)benzoic acid can act not only as hydrogen bond acceptors but also as hydrogen bond donors, which make it a wonderful candidate for the construction of supramolecular networks. The crystal structure consists of the mononuclear molecules. The coordinating 3-(sulfonyl-glycine)benzoic acid exists as a monoanion acting as a monodentate ligand. In the complex, zinc atom is five-coordinated in a distorted trigonal-bipyramidal ZnO5 environment, in which the basal coordination sites are occupied by three oxygen atoms (O1, O1A, O7), with the bond lengths of 1.968(1) Å, 1.968(1) Å and 2.071(3) Å, respectively. The axial position is occupied by two oxygen atoms (O8, O8A) from water molecules, with the bond lengths of both 2.076(2) Å. There exist intermolecular hydrogen bonds between carboxylate oxygen atoms from C 6H5COO group (O···O distances of 2.635 Å), forming 1D hydrogen bonded chains in which six-membered-ring and mononuclear units are alternately arranged a...

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Hydrogen-bonded porous solid derived from trimesic amide

Cited by 77 publications

References 15 publications

An alternating chain of spider-like tris(peptides) stabilized by stacking and by N–H⋯N and N–H⋯OC hydrogen bonding

An alternating chain of spider-like tris(peptides) stabilized by stacking and by N–H⋯N and N–H⋯OC hydrogen bonding

Crystal structure of monoaqua(5-bromoisophthalato)(2,2'-bipyridine)- cobalt(II) semihydrate, Co(H₂O)(C₈H₃BrO₄)(C₁₀H₈N₂) · 0.5H₂O

Crystal structure of triaqua-cis-bis((2-carboxybenzene)sulfonylglycinato) zinc(II), Zn(H2O)3(C9H8NO6S)2

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Hydrogen-bonded porous solid derived from trimesic amide

Cited by 77 publications

References 15 publications

An alternating chain of spider-like tris(peptides) stabilized by stacking and by N–H⋯N and N–H⋯OC hydrogen bonding

An alternating chain of spider-like tris(peptides) stabilized by stacking and by N–H⋯N and N–H⋯OC hydrogen bonding

Crystal structure of monoaqua(5-bromoisophthalato)(2,2'-bipyridine)- cobalt(II) semihydrate, Co(H2O)(C8H3BrO4)(C10H8N2) · 0.5H2O

Crystal structure of triaqua-cis-bis((2-carboxybenzene)sulfonylglycinato) zinc(II), Zn(H2O)3(C9H8NO6S)2

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Crystal structure of monoaqua(5-bromoisophthalato)(2,2'-bipyridine)- cobalt(II) semihydrate, Co(H₂O)(C₈H₃BrO₄)(C₁₀H₈N₂) · 0.5H₂O