scholarly journals Supramolecular Architecture of Chloranilate Salts with Organic Cations

2019 ◽  
Vol 92 (2) ◽  
pp. 297-305
Author(s):  
Krešimir Molčanov ◽  
Marijana Jurić ◽  
Lidija Androš Dubraja
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Organic Cations ◽  
Supramolecular Architecture ◽  
Aromatic Rings ◽  
Chloranilic Acid ◽  
Π Stacking ◽  
Different Types ◽  
1D Chains ◽  
Hydrogen Bonded

Four novel salts of chloranilic acid (H2CA; 3,6-dichloro-2,5-dihydroxy-1,4-quinone) with organic cations pyridinium (Hpy+), piperazinediium (H2ppz2+), 4,4'-bipyridinediium (H2bpy2+) and 1,10-phenanthrolinium (Hphen+) were prepared and structurally characterised: (Hpy)2CA (1), (H2ppz)CA (2), (H2bpy)CA·4H2O (3) and (Hphen)HCA·MeOH (4). Supramolecular architecture is based on extensive hydrogen bonding and π-stacking. The central motive is chloranilate dianion which acts as an acceptor of two bifurcated hydrogen bonds. Topology and dimensionality of hydrogen bonded networks can be tuned by use of different cations: thus discrete motives, 1D chains and 2D layers were observed. Three different types of π-stacks are present: aromatic stacks, quinoid stacks and stacks of alternating quinoid and aromatic rings.

Polymorphs of phenazine hexacyanoferrate(II) hydrate: supramolecular isomerism in a 2D hydrogen-bonded network

2021 ◽  
Vol 77 (2) ◽  
pp. 211-218
Author(s):  
Ivica Cvrtila ◽  
Vladimir Stilinović
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
The Other ◽  
Two Dimensional ◽  
Structural Motifs ◽  
Supramolecular Isomerism ◽  
Other Hand ◽  
Π Stacking ◽  
Hydrogen Bonded

The crystal structures of two polymorphs of a phenazine hexacyanoferrate(II) salt/cocrystal, with the formula (Hphen)3[H2Fe(CN)6][H3Fe(CN)6]·2(phen)·2H2O, are reported. The polymorphs are comprised of (Hphen)2[H2Fe(CN)6] trimers and (Hphen)[(phen)2(H2O)2][H3Fe(CN)6] hexamers connected into two-dimensional (2D) hydrogen-bonded networks through strong hydrogen bonds between the [H2Fe(CN)6]2− and [H3Fe(CN)6]− anions. The layers are further connected by hydrogen bonds, as well as through π–π stacking of phenazine moieties. Aside from the identical 2D hydrogen-bonded networks, the two polymorphs share phenazine stacks comprising both protonated and neutral phenazine molecules. On the other hand, the polymorphs differ in the conformation, placement and orientation of the hydrogen-bonded trimers and hexamers within the hydrogen-bonded networks, which leads to different packing of the hydrogen-bonded layers, as well as to different hydrogen bonding between the layers. Thus, aside from an exceptional number of symmetry-independent units (nine in total), these two polymorphs show how robust structural motifs, such as charge-assisted hydrogen bonding or π-stacking, allow for different arrangements of the supramolecular units, resulting in polymorphism.

scholarly journals N-Methyl-N-nitroso-p-toluenesulfonamide

2014 ◽  
Vol 70 (7) ◽  
pp. o782-o782
Author(s):  
Kartik Rai ◽  
Vincent Wu ◽  
Priya Gupta ◽  
David A. Laviska ◽  
Benny C. Chan
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Methyl Groups ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Compound C ◽  
Π Stacking ◽  
Centroid Distance

The crystal structure of the title compound, C8H10N2O3S, displays predominant C—H...O hydrogen-bonding and π–π stacking interactions. The hydrogen bonds are between the O atoms of the sulfonyl group and H atoms on methyl groups. The π–π stacking interactions occur between adjacent aromatic rings, with a centroid–centroid distance of 3.868 (11) Å. These interactions lead to the formation of chains parallel to (101).

scholarly journals Hydrogen Bonded Charge Transfer Complex of Chloranilic Acid With Benzimidazole

2014 ◽  
Vol 70 (a1) ◽  
pp. C1826-C1826
Author(s):  
Prof. Emmanuel Marfo-Owusu ◽  
Dr. Amber Thompson
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Charge Transfer ◽  
Hydrogen Bonds ◽  
Charge Transfer Complex ◽  
Intramolecular Hydrogen Bonding ◽  
Monoclinic Space Group ◽  
Chloranilic Acid ◽  
Hydrogen Bonding Network ◽  
Hydrogen Bonded

The crystal structure of 1:1:1 complex of chloranilic acid with benzimidazole and water determined by X-ray diffraction methods is reported. It crystallizes in the monoclinic (space group, P21/c) crystal system. Both chloranilic acid and benzimidazole molecules adopt a face-to-face stacking arrangement along the b-axis. An interaction beween adjacent layers is a π...π stacking interactions between chloranilic acid molecules. The dihedral angle between the interacting chloranilic acid ring planes is only 1.22 (7)0with an interplanar spacing between C10...C12 (3.383 (16) Å) and C13...C15 (3.351 (14) Å ). Water influences proton transfer in the hydrogen bonded charge transfer complex, and contributes to generating increased number of hydrogen bonds utilized in the stabilzaation of the crystal structure of the complex. Water serves as an efficient bridge between the chloranilic acid molecules through O-H...O intermolecular hydrogen bonds to form a zigzag channel, as well as directly linking chloranilic acid molecules with benzimidazole molecules which are strongly entrapped within the zigzag channel by intermolecular hydrogen bonding network involving the N-H...O, C-H...O, and C-H...Cl interactions. In the chloranilate anion structure, an intramolecular hydrogen bonding involving O2-H7 and O1 (dO2... O1 and dH7... O1 = 2.670 (12) and 2.25 Å) occurs. The supramolecular architecture of the hydrogen bonded charge complex exhibits a three-dimensional hydrogen bonding network

scholarly journals (E)-2-[2-(3-Nitrophenyl)ethenyl]quinolin-8-ol

2013 ◽  
Vol 69 (11) ◽  
pp. o1651-o1652
Author(s):  
Mathias Schulze ◽  
Wilhelm Seichter ◽  
Edwin Weber
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Title Compound ◽  
Stacking Interactions ◽  
Supramolecular Architecture ◽  
Compound C ◽  
Π Stacking ◽  
The Mean ◽  
Quinoline Moiety

In the title compound, C17H12N2O3, the mean planes of the benzene ring and the quinoline moiety are inclined to one another by 11.0 (1)°. The nitro substituent is twisted at an angle of 7.9 (2)° with respect to the attached benzene ring. Intramolecular O—H...N and C—H...N hydrogen bonds occur. The crystal is constructed of molecular stacks without involvement of π-stacking interactions, but showing interstack associationviaO—H...O and C—H...O hydrogen bonding. Thus, the supramolecular architecture of the crystal results from stacked molecules stabilized by hydrogen bonding between the stacks.

scholarly journals Bis(thiocyanato-κN)[tris(pyridin-2-ylmethyl)amine-κ4N]iron(II)

2014 ◽  
Vol 70 (2) ◽  
pp. m35-m35
Author(s):  
Jing-Wei Dai ◽  
Zhao-Yang Li ◽  
Osamu Sato
Keyword(s):  
Hydrogen Bonds ◽  
Octahedral Geometry ◽  
Title Complex ◽  
Stacking Interactions ◽  
Supramolecular Architecture ◽  
Two Dimensional ◽  
Π Stacking ◽  
Centroid Distance ◽  
Solvent Molecules ◽  
Amine Ligand

In the title complex, [Fe(NCS)2(C18H18N4)], the FeIIcation is chelated by a tris(2-pyridylmethyl)amine ligand and coordinated by two thiocyanate anions in a distorted N6octahedral geometry. In the crystal, weak C—H...S hydrogen bonds and π–π stacking interactions between parallel pyridine rings of adjacent molecules [centroid–centroid distance = 3.653 (3) Å] link the molecules into a two-dimensional supramolecular architecture. The structure contains voids of 124 (9) Å3, which are free of solvent molecules.

5-Nitrosalicylaldehyde (2-hydroxybenzoyl)hydrazone

2006 ◽  
Vol 62 (7) ◽  
pp. o3026-o3027 ◽  
Author(s):  
Hong-Mei Xu ◽  
Shi-Xiong Liu
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Crystal Packing ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Compound C ◽  
Π Stacking

The molecule of the title compound, C14H11N3O5, is approximately planar, the dihedral angles between the two aromatic rings being 4.63 (7)°. O—H...N, N—H...O and O—H...O hydrogen bonds and π–π stacking interactions help to consolidate the crystal packing.

scholarly journals Synthesis, Structural Characterization and Ligand-Enhanced Photo-Induced Color-Changing Behavior of Two Hydrogen-Bonded Ho(III)-Squarate Supramolecular Compounds

Polymers ◽  
2019 ◽  
Vol 11 (8) ◽  
pp. 1369 ◽  
Author(s):  
Wang ◽  
Ke ◽  
Feng ◽  
Ho ◽  
Chang ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Uv Light ◽  
Squaric Acid ◽  
Water Molecules ◽  
Light Illumination ◽  
Supramolecular Architecture ◽  
Bridging Ligands ◽  
Coordination Modes ◽  
Oxygen Atoms ◽  
Hydrogen Bonded

Two coordination polymers (CPs) with chemical formulas, [Ho2(C4O4)2(C2O4)(H2O)8]·4H2O (1) and [Ho(C4O4)1.5(H2O)3] (2), (C4O42− = dianion of squaric acid, C2O42− = oxalate), have been synthesized and their structures were determined by single-crystal X-ray diffractometer (XRD). In compound 1, the coordination environment of Ho(III) ion is eight-coordinate bonded to eight oxygen atoms from two squarate, one oxalate ligands and four water molecules. The squarates and oxalates both act as bridging ligands with 1,2-bis-monodentate and bis-chelating coordination modes, respectively, connecting the Ho(III) ions to form a one-dimensional (1D) ladder-like framework. Adjacent ladders are interlinked via O–HO hydrogen bonding interaction to form a hydrogen-bonded two-dimensional (2D) layered framework and then arranged orderly in an AAA manner to construct its three-dimensional (3D) supramolecular architecture. In compound 2, the coordination geometry of Ho(III) is square-antiprismatic eight coordinate bonded to eight oxygen atoms from five squarate ligands and three water molecules. The squarates act as bridging ligands with two coordination modes, 1,2,3-trismonodentate and 1,2-bis-monodentate, connecting the Ho(III) ions to form a 2D bi-layered framework. Adjacent 2D frameworks are then parallel stacked in an AAA manner to construct its 3D supramolecular architecture. Hydrogen bonding interactions between the squarate ligands and coordinated water molecules in 1 and 2 both play important roles on the construction of their 3D supramolecular assembly. Compounds 1 and 2 both show remarkable ligand-enhanced photo-induced color-changing behavior, with their pink crystals immediately turning to yellow crystals under UV light illumination.

Supramolecular structures of N 4-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines

2003 ◽  
Vol 59 (2) ◽  
pp. 263-276 ◽  
Author(s):  
Manuel Melguizo ◽  
Antonio Quesada ◽  
John N. Low ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Electronic Structures ◽  
Supramolecular Structure ◽  
Supramolecular Structures ◽  
Stacking Interactions ◽  
Molecular Electronic ◽  
Π Stacking

The molecular and supramolecular structures of eight N 4-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines are discussed, along with one analogue containing no nitroso substituent. The nitroso derivatives all exhibit polarized molecular-electronic structures leading to extensive charge-assisted hydrogen bonding between the molecules. The intermolecular interactions include hard hydrogen bonds of N—H...O and N—H...N types, together with O—H...O and O—H...N types in the monohydrate of 2-amino-6-benzyloxy-4-piperidino-5-nitrosopyrimidine, soft hydrogen bonds of C—H...O, C—H...π(arene) and N—H...π(arene) types and aromatic π...π stacking interactions. The predominant supramolecular structure types take the form of chains and sheets, but no two of the structures determined here exhibit the same combination of hydrogen-bond types.

Cinnamic acid hydrogen bonds to isoniazid andN′-(propan-2-ylidene)isonicotinohydrazide, anin situreaction product of isoniazid and acetone

2014 ◽  
Vol 70 (4) ◽  
pp. 392-395 ◽  
Author(s):  
Inese Sarcevica ◽  
Liana Orola ◽  
Mikelis V. Veidis ◽  
Sergey Belyakov
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Cinnamic Acid ◽  
Slow Evaporation ◽  
Hydrogen Bonded

A new polymorph of the cinnamic acid–isoniazid cocrystal has been prepared by slow evaporation, namely cinnamic acid–pyridine-4-carbohydrazide (1/1), C9H8O2·C6H7N3O. The crystal structure is characterized by a hydrogen-bonded tetrameric arrangement of two molecules of isoniazid and two of cinnamic acid. Possible modification of the hydrogen bonding was investigated by changing the hydrazide group of isoniazidviaanin situreaction with acetone and cocrystallization with cinnamic acid. In the structure of cinnamic acid–N′-(propan-2-ylidene)isonicotinohydrazide (1/1), C9H8O2·C9H11N3O, carboxylic acid–pyridine O—H...N and hydrazide–hydrazide N—H...O hydrogen bonds are formed.

scholarly journals Hydrogen-bonding patterns in 2-amino-4,6-dimethoxypyrimidine–4-aminobenzoic acid (1/1)

2006 ◽  
Vol 62 (7) ◽  
pp. o2976-o2978 ◽  
Author(s):  
Kaliyaperumal Thanigaimani ◽  
Packianathan Thomas Muthiah ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Carboxyl Group ◽  
Acid Molecule ◽  
Aminobenzoic Acid ◽  
Graph Set ◽  
Supramolecular Chain ◽  
Bonding Patterns ◽  
Hydrogen Bonded

In the title cocrystal, C6H9N3O2·C7H7NO2, the 2-amino-4,6-dimethoxypyrimidine molecule interacts with the carboxyl group of the 4-aminobenzoic acid molecule through N—H...O and O—H...N hydrogen bonds, forming a cyclic hydrogen-bonded motif [R 2 2(8)]. This motif further self-organizes through N—H...O hydrogen bonds to generate an array of six hydrogen bonds with the rings having the graph-set notation R 2 3(6), R 2 2(8), R 4 2(8), R 2 2(8) and R 2 3(6). The 4-aminobenzoic acid molecules self-assemble via N—H...O hydrogen bonds to form a supramolecular chain along the c axis.

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