scholarly journals Simple Acyclic Molecules Containing a Single Charge-Assisted O–H Group Can Recognize Anions in Acetonitrile:water Mixtures

2021 ◽  
Author(s):  
Rosemary Goodwin ◽  
Mitchell Blyth ◽  
Alfred Fung ◽  
Leesa Smith ◽  
Philip Norcott ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Solvent Mixture ◽  
Association Constants ◽  
Chloride Binding ◽  
Single Charge ◽  
Anion Coordination ◽  
Low Solubility

Hydroxypyridinium and hydroxyquinolinium compounds containing acidic O–H groups attached to a cationic aromatic scaffold were synthesized, i.e. N-methyl-3-hydroxypyridinium (1+) and N-methyl-8-hydroxyquinolinium (2+). These very simple compounds are capable of binding to chloride very strongly in CD3CN and with moderate strength in 9:1 CD3CN:D2O. Comparison with known association constants reveal that 1+ and 2+ bind chloride in CD3CN or CD3CN:D2O with comparable affinities to receptors containing significantly more hydrogen bond donors and/or higher positive charges. Crystal structures of both compounds with coordinating anions were obtained, and feature short O–H∙∙∙anion hydrogen bonds. A receptor containing two hydroxyquinolinium groups was also prepared. While the low solubility of this compound caused difficulties, we were able demonstrate chloride binding in a competitive 1:1 CD3CN:CD3OD solvent mixture. Addition of sulfate to this compound results in the formation of a crystallographically-characterised solid state anion coordination polymer.

scholarly journals Simple Acyclic Molecules Containing a Single Charge-Assisted O–H Group Can Recognize Anions in Acetonitrile:water Mixtures

2021 ◽  
Author(s):  
Rosemary Goodwin ◽  
Mitchell Blyth ◽  
Alfred Fung ◽  
Leesa Smith ◽  
Philip Norcott ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Solvent Mixture ◽  
Association Constants ◽  
Chloride Binding ◽  
Single Charge ◽  
Anion Coordination ◽  
Low Solubility

Hydroxypyridinium and hydroxyquinolinium compounds containing acidic O–H groups attached to a cationic aromatic scaffold were synthesized, i.e. N-methyl-3-hydroxypyridinium (1+) and N-methyl-8-hydroxyquinolinium (2+). These very simple compounds are capable of binding to chloride very strongly in CD3CN and with moderate strength in 9:1 CD3CN:D2O. Comparison with known association constants reveal that 1+ and 2+ bind chloride in CD3CN or CD3CN:D2O with comparable affinities to receptors containing significantly more hydrogen bond donors and/or higher positive charges. Crystal structures of both compounds with coordinating anions were obtained, and feature short O–H∙∙∙anion hydrogen bonds. A receptor containing two hydroxyquinolinium groups was also prepared. While the low solubility of this compound caused difficulties, we were able demonstrate chloride binding in a competitive 1:1 CD3CN:CD3OD solvent mixture. Addition of sulfate to this compound results in the formation of a crystallographically-characterised solid state anion coordination polymer.

scholarly journals 1-[N-Methyl-N-(Phenyl)amino]-3- (4-Methylphenyl)Thiourea

Molbank ◽  
10.3390/m1052 ◽  
2019 ◽  
Vol 2019 (1) ◽  
pp. M1052 ◽  
Author(s):  
Chien Yeo ◽  
Edward Tiekink
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Elemental Analysis ◽  
Title Compound ◽  
Molecular Conformation ◽  
Phenyl Hydrazine ◽  
X Ray ◽  
X Ray Crystallography

The title compound, 1-[N-methyl-N-(phenyl)amino]-3-(4-methylphenyl)thiourea (1), was synthesized by the reaction of 1-methyl-1-phenyl hydrazine and 4-tolyl isothiocyanate, and was characterized by spectroscopy (1H and 13C{1H} NMR, IR, and UV), elemental analysis as well as by single crystal X-ray crystallography. In the solid state, the molecule exists as the thioamide tautomer and features an anti-disposition of the thioamide–N–H atoms; an intramolecular N–H⋯N hydrogen bond is noted. The molecular conformation resembles that of the letter L. In the molecular packing, thioamide-N1–H⋯S1(thione) hydrogen bonds lead to centrosymmetric eight-membered {⋯HNCS}2 synthons. The dimers are assembled into a supramolecular layer in the bc-plane by phenyl- and methyl-C–H⋯π(phenyl) interactions.

Solid-state and Calculated Electronic Structure of 4-Acetylpyrazole

2014 ◽  
Vol 69 (7) ◽  
pp. 839-843 ◽  
Author(s):  
Guido D. Frey ◽  
Wolfgang W. Schoeller ◽  
Eberhardt Herdtweck
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Electronic Structure ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Carbonyl Group ◽  
Monoclinic Space Group ◽  
X Ray ◽  
Ribbon Structure

The crystal structure of 1-(1H-pyrazol-4-yl)ethanone (commonly known as 4-acetylpyrazole; C5H6N2O) was determined from single-crystal X-ray data at 173 K: monoclinic, space group P21/n (no. 14), a = 3.865(1), b = 5.155(1), c = 26.105(8) Å, β = 91.13(1)°, V = 520.0(2) Å3 and Z = 4. The adjacent molecules assemble into a wave-like ribbon structure in the solid state, linked by strong intermolecular N-H...N hydrogen bonds between the pyrazole rings and a weak C-H...O=C hydrogen bond involving the carbonyl group. The ribbons are stacked in the solid state via weak π interactions between the pyrazole rings.

scholarly journals Poly[[chlorido(1,10-phenanthroline-κ2N,N′)copper(II)]-μ3-1,1,3,3-tetracyano-2-ethoxypropenido-κ3N:N′:N′′]: coordination polymer sheets linked into bilayers by hydrogen bonds

2013 ◽  
Vol 70 (1) ◽  
pp. 19-22 ◽  
Author(s):  
Zouaoui Setifi ◽  
Fatima Setifi ◽  
Lahcen El Ammari ◽  
Malika El-Ghozzi ◽  
Jana Sopková-de Oliveira Santos ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Coordination Polyhedron ◽  
Title Compound ◽  
Phen Ligand ◽  
Bond Lengths ◽  
Electronic Delocalization ◽  
Polymer Sheets

In the title compound, [Cu(C9H5N4O)Cl(C12H8N2)]nor [Cu(tcnoet)Cl(phen)]n, where phen is 1,10-phenanthroline and tcnoet is 1,1,3,3-tetracyano-2-ethoxypropenide, the axially elongated (4 + 2) coordination polyhedron around the CuIIcentre contains N atoms from three different tcnoet ligands. The resulting coordination polymer takes the form of sheets which are linked in pairs by a single C—H...N hydrogen bond to form bilayers. The bond lengths provide evidence for significant bond fixation in the phen ligand and extensive electronic delocalization in the tcnoet ligand, where the two –C(CN)2units are rotated, in conrotatory fashion, out of the plane of the central C3O fragment.

scholarly journals On hydrogen bonding in 1,6-anhydro-β-D-glucopyranose (levoglucosan): X-ray and neutron diffraction and DFT study

2006 ◽  
Vol 62 (5) ◽  
pp. 912-918 ◽  
Author(s):  
Ľubomír Smrčok ◽  
Mariana Sládkovičová ◽  
Vratislav Langer ◽  
Chick C. Wilson ◽  
Miroslav Koóš
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Neutron Diffraction ◽  
Dft Calculations ◽  
Diffraction Data ◽  
Neutron Diffraction Study ◽  
Single Crystal Diffraction ◽  
X Ray

The geometry of hydrogen bonds in 1,6-anhydro-β-D-glucopyranose (levoglucosan) is accurately determined by refinement of time-of-flight neutron single-crystal diffraction data. Molecules of levoglucosan are held together by a hydrogen-bond array formed by a combination of strong O—H...O and supporting weaker C—H...O bonds. These are fully and accurately detailed by the neutron diffraction study. The strong hydrogen bonds link molecules in finite chains, with hydroxyl O atoms acting as both donors and acceptors of hydroxyl H atoms. A comparison of molecular and solid-state DFT calculations predicts red shifts of O—H and associated blue shifts of C—H stretching frequencies due to the formation of hydrogen bonds in this system.

A new one-dimensional ZnIIcoordination polymer based on 2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole and benzene-1,2-dicarboxylate

2015 ◽  
Vol 71 (11) ◽  
pp. 1017-1021 ◽  
Author(s):  
Qiu-Ying Huang ◽  
Wei Liu ◽  
Yi Yang ◽  
Xiang-Ru Meng
Keyword(s):  
Solid State ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Layered Structure ◽  
Heterocyclic Compounds ◽  
Room Temperature ◽  
Dimensional Chain ◽  
Two Dimensional ◽  
Hydrothermal Conditions ◽  
One Dimensional

Multidentate N-heterocyclic compounds form a variety of metal complexes with many intriguing structures and interesting properties. The title coordination polymer,catena-poly[zinc(II)-bis{μ-2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole}-κ2N3:N3′;N3′:N3-zinc(II)-bis(μ-benzene-1,2-dicarboxylato)-κ2O1:O2;κ3O1,O1′:O2], [Zn2(C8H4O4)2(C11H10N4)2]n, has been synthesized by the reaction of Zn(NO3)2with 2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole (imb) and benzene-1,2-dicarboxylic acid (H2bdic) under hydrothermal conditions. There are two crystallographically distinct imb ligands [imb(A) and imb(B)] in the structure which adopt very similar coordination geometries. The imb(A) ligand bridges two symmetry-related Zn1 ions, yielding a binuclear [(Zn1)2{imb(A)}2] unit, and the imb(B) ligand bridges two symmetry-related Zn2 ions resulting in a binuclear [(Zn2)2{imb(B)}2] unit. The above-mentioned binuclear units are further connected alternately by pairs of bridging bdic2−ligands, forming an infinite one-dimensional chain. These one-dimensional chains are further connected through N—H...O hydrogen bonds, leading to a two-dimensional layered structure. In addition, the title polymer exhibits good fluorescence properties in the solid state at room temperature.

A new two-dimensional ZnIIcoordination polymer constructed by a multidentate N-heterocyclic ligand and 5-carboxybenzene-1,3-dicarboxylate

2015 ◽  
Vol 71 (8) ◽  
pp. 701-705 ◽  
Author(s):  
Qiu-Ying Huang ◽  
Yi Yang ◽  
Xiang-Ru Meng
Keyword(s):  
Solid State ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Architecture ◽  
Two Dimensional ◽  
Tetrahedral Geometry ◽  
Heterocyclic Ligand ◽  
Distorted Tetrahedral Geometry ◽  
Dimensional Network

In the coordination polymer, poly[[{μ-1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole-κ2N:N′}(μ-5-carboxybenzene-1,3-dicarboxylato-κ2O1:O3)zinc(II)] dimethylformamide monosolvate pentahydrate], {[Zn(C9H4O6)(C11H10N4)]·C3H7NO·5H2O}n, the ZnIIion is coordinated by two N atoms from two symmetry-related 1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole (bmi) ligands and two O atoms from two symmetry-related 5-carboxybenzene-1,3-dicarboxylate (Hbtc2−) ligands in a slightly distorted tetrahedral geometry. The ZnIIions are bridged by Hbtc2−and bmi ligands, leading to a 4-connected two-dimensional network with the topological notation (44.62). Adjacent layers are further connected by 12 kinds of hydrogen bonds and also by π–π interactions, resulting in a three-dimensional supramolecular architecture in the solid state.

scholarly journals Persistent Superprotonic Conductivity in the Order of 10−1 S·cm−1 Achieved Through Thermally Induced Structural Transformation of a Uranyl Coordination Polymer

CCS Chemistry ◽  
2019 ◽  
Vol 1 (2) ◽  
pp. 197-206 ◽  
Author(s):  
Daxiang Gui ◽  
Wanchun Duan ◽  
Jie Shu ◽  
Fuwan Zhai ◽  
Ning Wang ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Coordination Polymer ◽  
High Performance ◽  
Hydrogen Bond Acceptor ◽  
Proton Conducting ◽  
Thermally Induced ◽  
High Proton ◽  
Conducting Materials ◽  
Testing Condition

Despite tremendous efforts having been made in the exploration of new high-performance proton-conducting materials, systems with superprotonic conductivity higher than 10−1 S·cm−1 are scarcely reported. We show here the utilization of bridging uranyl oxo atoms, traditionally termed cation–cation interaction (CCI), as the hydrogen bond acceptor to build a dense and ordered hydrogen bond network, affording a unique uranyl-based proton-conducting coordination polymer (H3O)4UO2(PO4)2 (HUP-1). This compound contains a densely connected hydronium network that is substantially stabilized by uranyl oxo atoms and exhibits high proton conductivities over a wide temperature range. At 98 °C, 98% relative humidity, a superprotonic conductivity of 1.02 × 10−1 S·cm−1 is observed for the system, one of the highest values reported for a solid-state proton-conducting material. This property originates from the thermally induced phase transformation from HUP-1 to another uranyl compound also with a CCI bond, (H3O)UO2PO4·(H2O)3 (HUP-2), accompanied by the partial generation of phosphorus acid that is further trapped in the structure of HUP-2, demonstrated by solid-state NMR analysis. The superprotonic conductivity of H3PO4@HUP-2 is persistent under the testing condition.

Competition between hydrogen bonds and halogen bonds: a structural study

2018 ◽  
Vol 42 (13) ◽  
pp. 10539-10547 ◽  
Author(s):  
Janaka C. Gamekkanda ◽  
Abhijeet S. Sinha ◽  
John Desper ◽  
Marijana Đaković ◽  
Christer B. Aakeröy
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Structural Study ◽  
Halogen Bond ◽  
Halogen Bonds ◽  
Hydrogen Bond Donors

O–H hydrogen-bond donors and R–CC–I halogen-bond donors are close competitors for suitable acceptor sites in solid-state assembly.

Poly[(μ3-benzene-1,4-dicarboxylato)di-μ-chlorido-(triethanolamine)dicadmium(II)]: a cadmium–halide coordination polymer with a hydrogen-bonded three-dimensional framework

2012 ◽  
Vol 68 (4) ◽  
pp. m109-m112 ◽  
Author(s):  
Xiyun He ◽  
Jianyi Lv ◽  
Guohai Xu
Keyword(s):  
Hydrogen Bond ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Hydrogen Bond Donor ◽  
One Dimensional ◽  
The One ◽  
Hydroxy Groups ◽  
Hydrogen Bonded

The structure of the title compound, [Cd2(C8H4O4)Cl2(C6H15NO3)]n, consists of one-dimensional chains in which each centrosymmetric tetranuclear Cd4Cl4O2cluster is terminated by two chelating triethanolamine (teaH3) ligands but linked to two adjacent clusters through four bridging benzene-1,4-dicarboxylate (bdc) ligands. The tetranuclear Cd4Cl4O2clusters are held togetherviabridging Cl and O atoms. Three directional hydrogen bonds from the multi-podal hydroxy groups of the teaH3ligand stabilize and extend the one-dimensional chains into a three-dimensional framework. All three hydroxy groups of the teaH3ligand form hydrogen bonds, illustrating the fact that the teaH3ligand can serve as an excellent hydrogen-bond donor.

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