Hydrogen bond-rigidified planar squaraine dye and its electronic and organic semiconductor properties

2020 ◽  
Vol 56 (68) ◽  
pp. 9890-9893
Author(s):  
Takeshi Maeda ◽  
Andreas Liess ◽  
Astrid Kudzus ◽  
Ana-Maria Krause ◽  
Matthias Stolte ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Organic Semiconductor ◽  
Squaric Acid ◽  
Squaraine Dyes ◽  
Planar Structures ◽  
Squaraine Dye ◽  
One Step ◽  
The One ◽  
Semiconductor Properties

The one-step reaction of a dicyanovinyl-functionalized squaric acid with Fischer bases afforded C2v symmetric squaraine dyes with rigid planar structures due to intramolecular N–H⋯O hydrogen bonds.

scholarly journals (3Z)-3-[(Z)-2-(2-Oxoindolin-3-ylidene)hydrazin-1-ylidene]indolin-2-one 0.17-hydrate

2014 ◽  
Vol 70 (6) ◽  
pp. o721-o721
Author(s):  
Yong-Hong Liu ◽  
Lei Zhao ◽  
Ming-Xuan Liu ◽  
Hai Lin ◽  
Jing-Jing Li
Keyword(s):  
Hydrogen Bonds ◽  
Microwave Irradiation ◽  
Organic Molecule ◽  
Condensation Reaction ◽  
Three Dimensional ◽  
Water Molecules ◽  
Inversion Symmetry ◽  
Compound C ◽  
One Step ◽  
The One

In the title compound, C16H10N4O2·0.17H2O, prepared by the one-step condensation reaction of isatin with hydrazine hydrate under microwave irradiation, the complete organic molecule is generated by crystallographic inversion symmetry and therefore exists in anS-transconformation. In the crystal, molecules are linked by N—H...O hydrogen bonds, generating a three-dimensional framework with [001] channels, which are occupied by the disordered water molecules.

scholarly journals 1,3-Bis{(E)-[4-(dimethylamino)benzylidene]amino}propan-2-ol: chain structure formation via an O—H...N hydrogen bond

2017 ◽  
Vol 73 (6) ◽  
pp. 813-816
Author(s):  
Augusto Rivera ◽  
Ingrid Miranda-Carvajal ◽  
Jaime Ríos-Motta ◽  
Michael Bolte
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Lone Electron Pair ◽  
Three Dimensional ◽  
Chain Structure ◽  
Compound C ◽  
Dimensional Network ◽  
Benzene Rings ◽  
The One

The asymmetric unit of the title compound, C21H28N4O, consists of two unique molecules linked by an O—H...N hydrogen bond. The conformation of both C=N bonds is E and the azomethine functional groups lie close to the plane of their associated benzene rings in each of the independent molecules. The dihedral angles between the two benzene rings are 83.14 (4) and 75.45 (4)°. The plane of the one of the N(CH3)2 units is twisted away from the benzene ring by 18.8 (2)°, indicating loss of conjugation between the lone electron pair and the benzene ring. In the crystal structure, O—H...N hydrogen bonds together with C—H...O hydrogen bonds link neighbouring supramolecular dimers into a three-dimensional network.

scholarly journals Crystal structure of 2-(azaniumylmethyl)pyridinium bis(hydrogen squarate)

2017 ◽  
Vol 73 (4) ◽  
pp. 586-589
Author(s):  
Nina Salamzadeh ◽  
Zeynep Demircioglu ◽  
Ufuk Korkmaz ◽  
Orhan Büyükgüngör
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Pyridine Ring ◽  
Pyridine Molecule ◽  
Squaric Acid ◽  
Asymmetric Unit ◽  
Pyridinium Cation ◽  
Compound C

The asymmetric unit of the title compound, C6H10N22+·2C4HO4−, comprises two hydrogen squarate (Hsq−; systematic name: 2-hydroxy-3,4-dioxocyclobutanolate) anions and a 2-(azaniumylmethyl)pyridinium dication. The squaric acid molecules each donate an H atom to the N atoms of the pyridine ring and the aminomethyl units of a 2-(aminomethyl)pyridine molecule, forming the 1:2 salt. The Hsq−anions are linked by strong O—H...O hydrogen bonds and an N—H...O hydrogen bond links the 2-(azaniumylmethyl)pyridinium cation to one of the squaric acid anions. The crystal structure features additional N—H...O and O—H...O hydrogen bonds, π–π stacking and unusual weak C—O...π(ring) interactions.

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.

General rules for the packing of hydrogen-bonded crystals as derived from the analysis of squaric acid anions: aminoaromatic nitrogen base co-crystals

2001 ◽  
Vol 57 (4) ◽  
pp. 591-598 ◽  
Author(s):  
Valerio Bertolasi ◽  
Paola Gilli ◽  
Valeria Ferretti ◽  
Gastone Gilli
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Squaric Acid ◽  
Nitrogen Base ◽  
General Application ◽  
General Rules ◽  
Simple Rules ◽  
Crystal Packings ◽  
Hydrogen Bonded

Preparation and single-crystal X-ray structure determination of three co-crystals of hydrogen squarate, HSQ−, with 2-aminopyrimidine, 3-aminopyridine and 4-aminopyridine, and one of squarate, SQ2-, with 8-aminoquinoline are reported. Their crystal packings are analyzed and discussed in terms of the intermolecular O—H...O, N—H...O/N and C—H...O hydrogen bonds formed. Although the fine details of the supramolecular architecture are barely rationalizable, the comparative analysis of the data makes it possible to suggest some simple rules that may be of general application for the packing of hydrogen-bonded crystals, i.e. Rule 1: `All hydrogen-bond acceptors available in a molecule will be engaged in hydrogen bonding as far as there are available donors'; Rule 2: `The hydrogen-bond acceptors will be saturated in order of decreasing strength of the hydrogen bonds formed'.

A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

2020 ◽  
Vol 24 (4) ◽  
pp. 465-471 ◽  
Author(s):  
Zita Rádai ◽  
Réka Szabó ◽  
Áron Szigetvári ◽  
Nóra Zsuzsa Kiss ◽  
Zoltán Mucsi ◽  
...  
Keyword(s):  
Quantum Chemical ◽  
Room Temperature ◽  
Phase Transfer ◽  
One Pot ◽  
Substrate Dependence ◽  
Triethylbenzylammonium Chloride ◽  
One Step ◽  
The Pudovik Reaction ◽  
The One ◽  
Solid Liquid

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.

Hydrogen bonds in N-(3-chloro-2-benzo[b]thienocarbonyl)- and N-(2-benzo[b]thienocarbonyl)-N'-monosubstituted thioureas

1987 ◽  
Vol 52 (11) ◽  
pp. 2673-2679 ◽  
Author(s):  
Oľga Hritzová ◽  
Peter Kutschy ◽  
Ján Imrich ◽  
Thomas Schöffmann
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Strong Hydrogen Bond ◽  
Cyclic Form ◽  
Thiourea Derivatives

N-(3-Chloro-2-benzo[b]thienocarbonyl)-N'-monosubstituted thiourea derivatives undergo photocyclizations with lower yields than those obtained from analogous N',N'-disubstituted derivatives. This decreased reactivity is caused by the existence of a six-membered cyclic form with the very strong hydrogen bond NH···O=C. The possibility of formation of various conformers has been found with N-(2-benzo[b]thienocarbonyl)-N'-monosubstituted thiourea derivatives as a consequence of the rotation around the C(2)-C(O) connecting line.

Crystal structure of tofacitinib dihydrogen citrate (Xeljanz®), (C16H21N6O)(H2C6H5O7)

2021 ◽  
pp. 1-8
Author(s):  
James A. Kaduk ◽  
Amy M. Gindhart ◽  
Thomas N. Blanton
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Powder Diffraction ◽  
Density Functional ◽  
Acid Group ◽  
Dimensional Network ◽  
Van Der Waals Contacts ◽  
Citrate Anion

The crystal structure of tofacitinib dihydrogen citrate (tofacitinib citrate) has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Tofacitinib dihydrogen citrate crystallizes in space group P212121 (#19) with a = 5.91113(1), b = 12.93131(3), c = 30.43499(7) Å, V = 2326.411(6) Å3, and Z = 4. The crystal structure consists of corrugated layers perpendicular to the c-axis. Within the layers, cation⋯anion and anion⋯anion hydrogen bonds link the fragments into a two-dimensional network parallel to the ab-plane. Between the layers, there are only van der Waals contacts. A terminal carboxylic acid group in the citrate anion forms a strong charge-assisted hydrogen bond to the ionized central carboxylate group. The other carboxylic acid acts as a donor to the carbonyl group of the cation. The citrate hydroxy group forms an intramolecular charge-assisted hydrogen bond to the ionized central carboxylate. Two protonated nitrogen atoms in the cation act as donors to the ionized central carboxylate of the anion. These hydrogen bonds form a ring with the graph set symbol R2,2(8). The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™ (PDF®).

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