scholarly journals One-Pot Synthesis, X-ray Single Crystal and Molecular Insight of Enaminone-Based β-Morpholino-/N-Methylpiperazinyl-/Pyrrolidinylpropiophenone

Crystals ◽  
2020 ◽  
Vol 10 (4) ◽  
pp. 282
Author(s):  
Assem Barakat ◽  
Saied M. Soliman ◽  
Matti Haukka ◽  
Abdullah Mohammed Al-Majid ◽  
Mohammad Shahidul Islam ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Single Crystal ◽  
Spectroscopic Properties ◽  
Secondary Amines ◽  
Dft Studies ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
One Pot Synthesis ◽  
Hirshfeld Analysis

One-pot synthesis of three enaminones, (E)-1-(4-chlorophenyl)-3-morpholinoprop-2-en-1-one 1, (E)-1-(4-chlorophenyl)-3-(4-methylpiperazin-1-yl)prop-2-en-1-one 2, and (E)-1-(4-chlorophenyl)-3-(pyrrolidin-1-yl)prop-2-en-1-one 3 were achieved. The synthetic protocol via three components reaction of p-chloroacetophenone with DMFDMA (N,N-dimethylformamid-dimethylacetal) and the corresponding secondary amines (morpholine/N-methylpiperazine/pyrrolidine) in dioxane under heating for 2.5–4 h at 102 °C yielded the requisite enaminones. This protocol has the advantage of no separation of intermediate, no need for column purification with quantitative yield for the target compounds. The chemical features of the β-enaminones 1–3 were assigned by NMR. β-Enaminones 1, and 2 were assigned by single crystal X-ray diffraction technique. The intermolecular interactions in the crystal structures were analyzed quantitatively using Hirshfeld analysis. The Cl…H and O…H hydrogen bonds are common in both compounds while the C-H…π and N…H contacts are more significant in 2 than 1. DFT studies were investigated to show the electronic and spectroscopic properties (NMR and UV-Vis) of the studied systems.

scholarly journals A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

2015 ◽  
Vol 11 ◽  
pp. 2125-2131 ◽  
Author(s):  
Mingxing Liu ◽  
Jiarong Li ◽  
Hongxin Chai ◽  
Kai Zhang ◽  
Deli Yang ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Ir Spectroscopy ◽  
Single Crystal ◽  
Reaction Pathways ◽  
X Ray Diffraction ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
X Ray ◽  
One Pot Synthesis

An efficient one-pot synthesis of pyrazolo[3,4-d]pyrimidine derivatives by the four-component condensation of hydrazines, methylenemalononitriles, aldehydes and alcohols has been developed via two different reaction pathways. The structures of target products were characterized by IR spectroscopy, NMR (1H and 13C) spectroscopy and HRMS (ESI) spectrometry. The crystal structure of 4-ethoxy-6-(2-nitrophenyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine was determined by single crystal X-ray diffraction.

scholarly journals One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

2020 ◽  
Vol 16 ◽  
pp. 1447-1455 ◽  
Author(s):  
Gui-Feng Kang ◽  
Gang Zhang
Keyword(s):  
Single Crystal ◽  
Dual Role ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
One Pot ◽  
Diverse Range ◽  
X Ray ◽  
One Pot Synthesis ◽  
Synthetic Strategy

A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction.

One-pot Synthesis of 3-Aryl-substituted 1-Hydroxy-2-acylindolizines

2012 ◽  
Vol 67 (11) ◽  
pp. 1151-1158 ◽  
Author(s):  
Tobias Kloubert ◽  
Robert Kretschmer ◽  
Helmar Görls ◽  
Sven Krieck ◽  
Matthias Westerhausen
Keyword(s):  
Hydrogen Bonds ◽  
Crystalline State ◽  
Ph Value ◽  
Structural Information ◽  
X Ray Diffraction ◽  
Intermolecular Hydrogen Bonds ◽  
One Pot ◽  
X Ray ◽  
One Pot Synthesis ◽  
Substituted 1

A new method for the formation of C-C bonds in a one-pot synthesis of 1-hydroxy-2-acyl-3- arylindolizines (acyl: 2-pyridylformyl, thienylformyl; aryl: phenyl, pyridyl, thienyl) from the reaction of 1,3-diketones with aldehydes has been evaluated. X-Ray diffraction studies of single crystals have provided structural information about the so-formed indolizines. In the crystalline state, the hydroxyl units form intra- or intermolecular hydrogen bonds to the acyl functionalities. The color of these indolizines depends on the pH value of the solvent.

One-pot concomitant preparation of two copper(II) coordination polymers with different configurations of bridging bithiophene ligands

2020 ◽  
Vol 76 (1) ◽  
pp. 37-43
Author(s):  
Zhi-Qiang Shi ◽  
Ning-Ning Ji ◽  
Hai-Liang Hu
Keyword(s):  
Hydrogen Bonds ◽  
Single Crystal ◽  
Coordination Polymers ◽  
Three Dimensional ◽  
Chain Structure ◽  
X Ray Diffraction ◽  
Compound I ◽  
One Pot ◽  
X Ray ◽  
Vis Spectroscopy

By employing the conjugated bithiophene ligand 5,5′-bis(1H-imidazol-1-yl)-2,2′-bithiophene (bibp), which can exhibit trans and cis conformations, two different CuII coordination polymers, namely, poly[[μ-5,5′-bis(1H-imidazol-1-yl)-2,2′-bithiophene-κ2 N:N′](μ2-4,4′-oxydibenzoato-κ2 O:O′)copper(II)], [Cu(C14H8O5)(C14H10N4S2)] n or [Cu(bibp)(oba)] n , (I), and catena-poly[μ-aqua-bis[μ-5,5′-bis(1H-imidazol-1-yl)-2,2′-bithiophene-κ2 N:N′]bis(μ3-4,4′-oxydibenzoato)-κ3 O:O′:O′′;κ4 O:O′,O′′:O′-dicopper(II)], [Cu2(C14H8O5)2(C14H10N4S2)(H2O)] n or [Cu2(bibp)(oba)2(H2O)] n , (II), have been prepared through one-pot concomitant crystallization and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis, powder X-ray diffraction (PXRD) and thermogravimetric (TG) analysis. Single-crystal X-ray diffraction indicates that the most interesting aspect of the structure is the existence of sole trans and cis conformations of the bibp ligand in a single net of (I) and (II), respectively. Compound (I) displays a threefold interpenetrating three-dimensional framework with a 4-connected {65.8} cds topology, whereas (II) features a one-dimensional chain structure. In the crystal of (II), the polymeric chains are further extended through C—H...O hydrogen bonds and C—H...π interactions into a three-dimensional supramolecular architecture. In addition, strong intramolecular O—H...O hydrogen bonds formed between the bridging water molecules and the carboxylate O atoms improve the stability of the framework of (II). Furthermore, solid-state UV–Vis spectroscopy experiments show that compounds (I) and (II) exhibit optical band gaps which are characteristic for optical semiconductors, with values of 2.70 and 2.26 eV, respectively.

scholarly journals Synthesis and crystallographic characterization of N-allyl-N-benzyl-4-methylbenzenesulfonamide

2020 ◽  
Vol 11 (3) ◽  
pp. 245-249
Author(s):  
Brock Anton Stenfors ◽  
Felix Nyuangem Ngassa
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Primary Amine ◽  
X Ray Diffraction ◽  
One Pot ◽  
Synthetic Process ◽  
X Ray ◽  
Cell Parameters

N-Benzyl-4-methylbenzenesulfonamides were prepared via a two-step synthetic process involving the treatment of 4-methylbenzenesulfonyl chloride with a primary amine to give the corresponding 4-methylbenzenesulfonamide. Benzylation of the sulfonamide affords the substituted N-benzyl-4-methylbenzenesulfonamides. The similarities between the two steps of synthesis lend credence to the development of a one-pot synthesis of substituted N-benzyl-4-methylbenzenesulfonamides from 4-methylbenzenesulfonyl chloride. This method was applied to the synthesis of N-allyl-N-benzyl-4-methylbenzenesulfonamide and characterized through spectroscopic and crystallographic means. The crystal structure of N-allyl-N-benzyl-4-methylbenzenesulfonamide was obtained by single-crystal X-ray diffraction. The crystal structure reveals an orthorhombic Pna21 space group with cell parameters a = 18.6919 (18) Å, b = 10.5612 (10) Å, c = 8.1065 (8) Å, V = 1600.3 (3) Å3 and Z = 4, T = 173.15 K, μ(MoKα) = 0.206 mm-1, Dcalc = 1.251 g/cm3, 14455 reflections measured (4.36° ≤ 2Θ ≤ 54.96°), 3619 unique (Rint = 0.0439, Rsigma = 0.0429) which were used in all calculations. The final R1 was 0.0428 (I > 2σ(I)) and wR2 was 0.1079 (all data). Molecules are linked through C-H···N hydrogen bonds and C-H···π interactions.

One-Pot Synthesis of a Cyclic Pyrene Octamer from Two Bifunctionalized Pyrene Monomers

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 344-347
Author(s):  
Hiroko Yamada ◽  
Naoki Aratani ◽  
Peifeng Mei ◽  
Ryo Kurosaki ◽  
Akinobu Matsumoto
Keyword(s):  
Molecular Structure ◽  
Single Crystal ◽  
Diffraction Analysis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
One Pot Synthesis ◽  
Cross Coupling Reaction

AbstractA 2,2′-tert-butyl-5,9-6′,8′-cyclooctameric pyrenylene ([8]CP) was synthesized by a one-pot Suzuki–Miyaura cross-coupling reaction from two kinds of bifunctionalized monomers, as a rare example of a cyclic octamer. The octameric molecular structure of [8]CP was revealed by single-crystal X-ray diffraction analysis.

Thermal-induced transformation of glutamic acid to pyroglutamic acid and self-cocrystallization: a charge–density analysis

2022 ◽  
Vol 78 (2) ◽  
Author(s):  
Sehrish Akram ◽  
Arshad Mehmood ◽  
Sajida Noureen ◽  
Maqsood Ahmed
Keyword(s):  
Hydrogen Bonds ◽  
Glutamic Acid ◽  
Single Crystal ◽  
Diffraction Data ◽  
Density Functional ◽  
Quantitative Estimation ◽  
Topological Analysis ◽  
Pyroglutamic Acid ◽  
X Ray Diffraction ◽  
X Ray

Thermal-induced transformation of glutamic acid to pyroglutamic acid is well known. However, confusion remains over the exact temperature at which this happens. Moreover, no diffraction data are available to support the transition. In this article, we make a systematic investigation involving thermal analysis, hot-stage microscopy and single-crystal X-ray diffraction to study a one-pot thermal transition of glutamic acid to pyroglutamic acid and subsequent self-cocrystallization between the product (hydrated pyroglutamic acid) and the unreacted precursor (glutamic acid). The melt upon cooling gave a robust cocrystal, namely, glutamic acid–pyroglutamic acid–water (1/1/1), C5H7NO3·C5H9NO4·H2O, whose structure has been elucidated from single-crystal X-ray diffraction data collected at room temperature. A three-dimensional network of strong hydrogen bonds has been found. A Hirshfeld surface analysis was carried out to make a quantitative estimation of the intermolecular interactions. In order to gain insight into the strength and stability of the cocrystal, the transferability principle was utilized to make a topological analysis and to study the electron-density-derived properties. The transferred model has been found to be superior to the classical independent atom model (IAM). The experimental results have been compared with results from a multipolar refinement carried out using theoretical structure factors generated from density functional theory (DFT) calculations. Very strong classical hydrogen bonds drive the cocrystallization and lend stability to the resulting cocrystal. Important conclusions have been drawn about this transition.

On the Reaction of ortho-Diphenoquinone Valence Isomers with Primary and Secondary Amines. X-Ray Structure Analysis of a 2,3-Dihydro-1H-azepinone and its Photochemical and Oxidative Conversion Products

1979 ◽  
Vol 32 (9) ◽  
pp. 1931 ◽  
Author(s):  
H Becker ◽  
K Gustafsson ◽  
CL Raston ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Secondary Amines ◽  
Reaction Products ◽  
Oxidative Conversion ◽  
X Ray Diffraction ◽  
X Ray ◽  
Primary And Secondary Amines ◽  
Diffraction Structure ◽  
Structure Determinations ◽  
Photochemical Isomerization

Single-crystal X-ray diffraction structure determinations are reported for three reaction products and photoisomers formed from reactions between an o-diphenoquinone valence isomer and primary and secondary amines, namely: 3,5-di-t-butyl-7-(3,5-di-t-butyl-2-hydroxyphenyl)-1-methyl-2,3-dihydro-1H-azepin-2-one (8; R1 = R2 = But, R3 = Me), its photochemical isomerization product 4,6-di-t-butyl-1-(3,5-di-t-butyl-2-hydroxyphenyl)-2-methyl-2-azabicyclo[3,2,0]hept-6-en-3-one (9; R1 = R2 = But, R3 = Me) and 4',5,7-tri-t-butyl-3'-(2,2-dimethylpropionyl)-1'-methylspiro[benzofuran-3(2H)-2'- pyrrolidinel-2,5'-dione (12; R1 = R2 = But, R3 = Me).

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.

scholarly journals High pressure studies of L-Serine-L-Ascorbic acid co-crystal

2014 ◽  
Vol 70 (a1) ◽  
pp. C988-C988
Author(s):  
Sergey Arkhipov ◽  
Boris Zakharov ◽  
Elena Boldyreva
Keyword(s):  
High Pressure ◽  
Ascorbic Acid ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Crystal Engineering ◽  
Mixed Crystals ◽  
Study Phase ◽  
X Ray Diffraction ◽  
X Ray ◽  
Wide Range

"Experiments for studying crystalline materials under extreme conditions are a powerful tool for investigating ""structure-property"" relationships. They also give information on the behavior of hydrogen bonds and are important both for materials science and crystal engineering. In addition, many processes in the living organisms are also related to mechanical stress. One of the most interesting tasks is to identify factors which influence the stability of a structure, or a part of the structure, at high pressure. Experiments on the systematic study of compounds in a wide range of pressures allow us to accumulate data that can be used to solve this problem. For a more complete picture, the mixed crystals of the selected compound are studied. Investigation of mixed crystals and cocrystals of interest can be compared with the crystals of individual compounds. We have chosen the structure of L-serine - L-ascorbic acid to be compared with those of L-serine and L-ascorbic acids for such a study. Phase transitions were previously reported to be induced by increasing pressure in both L-serine [1] and L-ascorbic acid [2]; moreover, the structure of L-serine was followed at multiple pressures by single-crystal and powder X-ray diffraction[3]. L-serine – L-ascorbic acid co-crystal was studied in the pressure range 0-5.4 GPa (at multiple points at every 0.5-0.7 GPa) by single-crystal X-ray diffraction and Raman spectroscopy. A phase transition has been detected and some rearrangement in the network of hydrogen bonds was observed. The high pressure data were compared with those for the individual structures of the L-serine and L-ascorbic acid. This work was supported by RFBR (grants 12–03-31541, 14-03-31866, 13-03-92704, 14-03-00902 ), Ministry of Science and Education of Russia and Russian Academy of Sciences."

Sign in / Sign up

Export Citation Format

Share Document