A molecular roundabout: triple cyclically arranged hydrogen bonds in light of experiment and theory

2018 ◽  
Vol 42 (24) ◽  
pp. 19467-19477 ◽  
Author(s):  
Agnieszka Kwocz ◽  
Jarosław Jan Panek ◽  
Aneta Jezierska ◽  
Łukasz Hetmańczyk ◽  
Andrzej Pawlukojć ◽  
...  
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Schiff Bases ◽  
Dft Studies ◽  
X Ray

This paper dwells on the synthesis and diverse studies of cyclically arranged hydrogen bridges in tris-hydroxy aryl Schiff bases. Experimental (IINS, IR, Raman and X-ray) and theoretical (CPMD, DFTP and DFT) studies of tris-hydroxy aryl Schiff bases have been performed in the solid state.

scholarly journals Tautomerism and Self-Association in the Solution of New Pinene-Bipyridine and Pinene-Phenanthroline Derivatives

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 298
Author(s):  
Atena B. Solea ◽  
Ivan Cornu ◽  
Vera Deneva ◽  
Aurelien Crochet ◽  
Katharina M. Fromm ◽  
...  
Keyword(s):  
Solid State ◽  
Dft Calculations ◽  
Structure Determination ◽  
Tautomeric Equilibrium ◽  
Dft Studies ◽  
X Ray ◽  
Vis Spectroscopy ◽  
Self Association

Two novel pinene-type ligands have been synthesized and their tautomeric and self-associating behavior studied in solution and in the solid state. The first ligand, an acetylated derivative of 5,6-pinene-bipyridine, displays keto-enol tautomerism in solution. This tautomeric equilibrium was studied by NMR and UV-Vis spectroscopy in various solvents, and the results were compared with the ones obtained through DFT calculations. The second ligand was obtained by an unusual oxidation of the phenanthroline unit of a pinene-phenanthroline derivative. This compound exists as a single tautomer in solution and aggregates both in solution (as observed by NMR) and in the solid state through H-bonding as observed by X-ray structure determination and confirmed by DFT studies.

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.

scholarly journals The Importance of CH···X (X = O, π) Interaction of a New Mixed Ligand Cu(II) Coordination Polymer: Structure, Hirshfeld Surface and Theoretical Studies

Crystals ◽  
2018 ◽  
Vol 8 (12) ◽  
pp. 455 ◽  
Author(s):  
Saikat Seth
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Noncovalent Interactions ◽  
Carbonyl Oxygen ◽  
Hirshfeld Surface ◽  
Mixed Ligand ◽  
Binding Energies ◽  
Zigzag Chain ◽  
X Ray ◽  
Π Interactions

In this study, a new equimolar (1:1:1) mixed ligand Cu(II) polymer, [Cu(IDA)(ImP)]n (1) with iminodiacetato (IDA) and imidazo[1,2-a]-pyridine (ImP) was synthesized and characterized by single crystal X-ray diffraction analysis. X-ray crystallography reveals that compound (1) consists of polymeric zigzag chain along [010] the carboxylate carbonyl oxygen atom by two-fold symmetry screw axis. The solid-state structure is stabilized through C–H···O hydrogen bonds and C–H···π interactions that lead the molecules to generate two-dimensional supramolecular assemblies. The intricate combinations of hydrogen bonds and C–H···π interactions are fully described along with computational studies. A thorough analysis of Hirshfeld surface and fingerprint plots elegantly quantify the interactions involved within the structure. The binding energies associated with the noncovalent interactions observed in the crystal structure and the interplay between them were calculated using theoretical DFT calculations. Weak noncovalent interactions were analyzed and characterized using Bader’s theory of ‘‘atoms-in-molecules’’ (AIM). Finally, the solid-state supramolecular assembly was characterized by the “Noncovalent Interaction” (NCI) plot index.

Two new CdII MOFs of 1,4-bis(1H-benzimidazol-1-yl)butane and flexible dicarboxylate ligands: luminescence sensing towards Fe3+

2020 ◽  
Vol 76 (11) ◽  
pp. 1024-1033
Author(s):  
Fang-Hua Zhao ◽  
Shi-Yao Li ◽  
Wen-Yu Guo ◽  
Zi-Hao Zhao ◽  
Xiao-Wen Guo ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Layer Structure ◽  
Three Dimensional ◽  
Supramolecular Network ◽  
Two Dimensional ◽  
X Ray Diffraction ◽  
X Ray ◽  
Vis Spectroscopy

Two new CdII MOFs, namely, two-dimensional (2D) poly[[[μ2-1,4-bis(1H-benzimidazol-1-yl)butane](μ2-heptanedioato)cadmium(II)] tetrahydrate], {[Cd(C7H10O4)(C18H18N4)]·4H2O} n or {[Cd(Pim)(bbimb)]·4H2O} n (1), and 2D poly[diaqua[μ2-1,4-bis(1H-benzimidazol-1-yl)butane](μ4-decanedioato)(μ2-decanedioato)dicadmium(II)], [Cd2(C10H16O4)2(C18H18N4)(H2O)2] n or [Cd(Seb)(bbimb)0.5(H2O)] n (2), have been synthesized hydrothermally based on the 1,4-bis(1H-benzimidazol-1-yl)butane (bbimb) and pimelate (Pim2−, heptanedioate) or sebacate (Seb2−, decanedioate) ligands. Both MOFs were structurally characterized by single-crystal X-ray diffraction. In 1, the CdII centres are connected by bbimb and Pim2− ligands to generate a 2D sql layer structure with an octameric (H2O)8 water cluster. The 2D layers are further connected by O—H...O hydrogen bonds, resulting in a three-dimensional (3D) supramolecular structure. In 2, the CdII centres are coordinated by Seb2− ligands to form binuclear Cd2 units which are linked by bbimb and Seb2− ligands into a 2D hxl layer. The 2D layers are further connected by O—H...O hydrogen bonds, leading to an 8-connected 3D hex supramolecular network. IR and UV–Vis spectroscopy, thermogravimetric analysis and solid-state photoluminescence analysis were carried out on both MOFs. Luminescence sensing experiments reveal that both MOFs have good selective sensing towards Fe3+ in aqueous solution.

Notizen: Solid State Structure of N,N-Dibenzylhydroxylamine

1995 ◽  
Vol 50 (4) ◽  
pp. 699-701 ◽  
Author(s):  
Norbert W. Mitzel ◽  
Jürgen Riede ◽  
Klaus Angermaier ◽  
Hubert Schmidbaur
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Unit Cell ◽  
Monoclinic Space Group ◽  
State Structure ◽  
X Ray Diffraction ◽  
Space Group ◽  
Solid State Structure ◽  
X Ray

The solid-state structure of N,N-dibenzylhydroxylamine (1) has been determined by single crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P 21/n with four formula units in the unit cell. N,N-dibenzylhydroxylamine dimerizes to give N2O2H2 sixmembered rings as a result of the formation of two hydrogen bonds O - H ··· N in the solid state.

Supramolecular architectures in two 1:1 cocrystals of 5-fluorouracil with 5-bromothiophene-2-carboxylic acid and thiophene-2-carboxylic acid

2017 ◽  
Vol 73 (6) ◽  
pp. 481-485 ◽  
Author(s):  
Marimuthu Mohana ◽  
Packianathan Thomas Muthiah ◽  
Colin D. McMillen
Keyword(s):  
Solid State ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
X Ray Diffraction ◽  
Base Pairs ◽  
X Ray ◽  
Supramolecular Architectures ◽  
Acid Acid ◽  
Carboxylic Acid Dimer

In solid-state engineering, cocrystallization is a strategy actively pursued for pharmaceuticals. Two 1:1 cocrystals of 5-fluorouracil (5FU; systematic name: 5-fluoro-1,3-dihydropyrimidine-2,4-dione), namely 5-fluorouracil–5-bromothiophene-2-carboxylic acid (1/1), C5H3BrO2S·C4H3FN2O2, (I), and 5-fluorouracil–thiophene-2-carboxylic acid (1/1), C4H3FN2O2·C5H4O2S, (II), have been synthesized and characterized by single-crystal X-ray diffraction studies. In both cocrystals, carboxylic acid molecules are linked through an acid–acid R 2 2(8) homosynthon (O—H...O) to form a carboxylic acid dimer and 5FU molecules are connected through two types of base pairs [homosynthon, R 2 2(8) motif] via a pair of N—H...O hydrogen bonds. The crystal structures are further stabilized by C—H...O interactions in (II) and C—Br...O interactions in (I). In both crystal structures, π–π stacking and C—F...π interactions are also observed.

Bindung von Metall-Ionen an Dipeptide: Struktur von Thallium(I)-(3-benzyl-6-carboxylatomethyl-2,5-diketopiperazin) / Binding of Metal Ions by Dipeptides: Structure of Thallium(I) 3-Benzyl-6-carboxylatomethyl-2,5-diketopiperazine

1992 ◽  
Vol 47 (7) ◽  
pp. 952-956
Author(s):  
P. Mikulcik ◽  
P. Bissinger ◽  
J. Riede ◽  
H. Schmidbaur
Keyword(s):  
Solid State ◽  
Nitrogen Atom ◽  
Hydrogen Bonds ◽  
Diffraction Analysis ◽  
Carbonyl Oxygen ◽  
State Structure ◽  
X Ray Diffraction ◽  
X Ray ◽  
Crystalline Product ◽  
Oxygen Atoms

Ester cleavage of aspartame (L-α-aspartyl-L-phenylalanine methylester) (1), by equimolar quantities of thallium ethoxide is accompanied by intramolecular cyclisation to give thallium 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine (2). The solid state structure of the crystalline product was determined by single-crystal X-ray diffraction analysis. The cations were found to form four short and four elongated contacts to seven oxygen atoms and one nitrogen atom of a total of six neighbouring 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine anions. There are inter-anionic hydrogen bonds only between the imino groups and the carbonyl oxygen atoms (O3, O4), featuring a pattern similar to that found for cytosine-guanosine contacts in DNA.

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.

Crystal and Molecular Structure of 3-(N-Methoxy-N-methylcarbamoyl)- 2,2,5,5-tetramethyl-1-oxy-pyrroline

2010 ◽  
Vol 65 (4) ◽  
pp. 475-478
Author(s):  
Guido D. Frey ◽  
Eberhardt Herdtweck
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal And Molecular Structure ◽  
Layer Structure ◽  
Nitroxide Radical ◽  
Orthorhombic Space Group ◽  
X Ray ◽  
Stable Nitroxide

The crystal structure of the stable nitroxide radical 3-(N-methoxy-N-methylcarbamoyl)-2,2,5,5- tetramethyl-1-oxy-pyrroline was determined from single-crystal X-ray data: orthorhombic, space group Pbca (no. 61), a = 9.0213(1), b = 12.8625(1), c = 21.2406(2) Å, V = 2464.68(4) Å3 and Z = 8. The adjacent molecules assemble to a supramolecular layer structure in the solid state, linked by two intermolecular C-H...O hydrogen bonds.

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