m-Terphenyl-3,3″-dioxo-derived oxacalixaromatics: synthesis, structure, and solvent encapsulation in the solid state

Hu, Wenjing; Liu, Long-Qing; Ma, Mingliang; Zhao, Xiao‐Li; Liu, Yahu A.; Mi, Xianqiang; Jiang, Biao; Wen, Ke

doi:10.1016/j.tet.2013.03.035

Cited by 9 publications

(4 citation statements)

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“…Oxacalixarenes remain a heavily investigated and compelling platform for the design of molecular receptors . Since early publications on their synthesis via nucleophilic aromatic substitution (S N Ar) methods, , researchers continue to diversify the accessible oxacalixarene architectures through modification of the nucleophilic and electrophilic aromatic starting materials. , The nucleophilic coupling partner, typically a resorcinol, is the most extensively varied reactant; oxacalixarenes have been constructed using dihydroxy-benzenes, naphthalenes, tryptycenes, and biphenylenes, terphenylenes, and related extended aromatic systems. , …”

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confidence: 99%

“…Alterations of the electrophilic component in S N Ar-based oxacalixarene formation have so far proven more limited in scope. Most commonly constructed using 2,4,6-trichloro-1,3,5-triazine or 1,5-difluoro-2,4-dinitrobenzene, successful macrocyclizations have also been reported using alternative nitrogen heterocycles including pyridines, pyrazines, pyrimidines, quinazolines, quinoxalines, and naphthyridines. , Frameworks composed of all-carbon arenes, however, continue to depend on 1,5-difluoro-2,4-dinitrobenzene as the electrophile, and this restricts the accessible functional group profiles of oxacalixarenes bearing all-carbon aromatic rings.…”

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confidence: 99%

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Single Step Synthesis of Acetylene-Substituted Oxacalix[4]arenes

et al. 2014

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Oxacalixarenes bearing acetylene groups are synthesized in a single step by nucleophilic aromatic substitution reactions of orcinol with various 1,5-diethynyl-2,4-difluorobenzenes. Thermodynamic equilibration of the cyclooligomer mixtures was accomplished for arylethynyl activating groups, leading to increased yields of the corresponding oxacalix[4]arenes. A 1,3-alternate macrocycle conformation is observed in the solid state, presenting a large V-shaped π-surface.

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confidence: 99%

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Single Step Synthesis of Acetylene-Substituted Oxacalix[4]arenes

et al. 2014

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“…1,5-Difluoro-2,4-dinitrobenzene (1) can also be used to enable the chromatographic resolution of chiral secondary alcohols [12]. More recently, difluorodinitrobenzene 1 has been extensively used as a monomer unit to prepare unusual azamacrocycles via cyclooligomerisation chemistry [13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

N1-(5-Fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine

Zissimou

Koutentis

2017

Molbank

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Treating 1,5-difluoro-2,4-dinitrobenzene (1) with N 1 -phenyl-5-(trifluoromethyl)benzene-1,2diamine (4) and N,N-diisopropylethylamine in EtOH at ca. 0 • C for 4 h affords a mixture of N 1 -(5-ethoxy-2,4-dinitrophenyl)-N 2 -phenyl-4-(trifluoromethyl)benzene-1,2-diamine (5) (38%) and N 1 -(5-fluoro-2,4-dinitrophenyl)-N 2 -phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) (51%) that can be separated by chromatography. Repeating the reaction in dichloromethane led to the sole formation of N 1 -(5-fluoro-2,4-dinitrophenyl)-N 2 -phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) in 96% yield.Abstract: Treating 1,5-difluoro-2,4-dinitrobenzene (1) with N 1 -phenyl-5-(trifluoromethyl)benzene-1,2-diamine (4) and N,N-diisopropylethylamine in EtOH at ca. 0 °C for 4 h affords a mixture of N 1 -(5-ethoxy-2,4-dinitrophenyl)-N 2 -phenyl-4-(trifluoromethyl)benzene-1,2-diamine (5) (38%) and N 1 -(5-fluoro-2,4-dinitrophenyl)-N 2 -phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) (51%) that can be separated by chromatography. Repeating the reaction in dichloromethane led to the sole formation of N 1 -(5-fluoro-2,4-dinitrophenyl)-N 2 -phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) in 96% yield.

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“…Recently, Aitipamula synthesized six new sulfamerazine solvates, considering the hydrogen bonded networks mediated by the solvent molecules. Particularly, some studies − have shown that methanol, acetone, benzene, dichloromethane, and toluene are the most frequent guest solvents when only organic structures are analyzed. These molecules are able to form multiple and stable hydrogen bond motifs with the organic solute molecule.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Methanol Molecule on the Stabilization of C₁₈H₁₈O₄ Crystal: Combined Theoretical and Structural Investigation

et al. 2014

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The ability of the chalcone, C18H18O4, to form solvates was theoretically and experimentally investigated. The unit cell with Z' > 1, composed of two independent chalcone molecules (α and β), shows the formation of a stable molecular complex which is related with the presence of methanol in this crystal lattice. Aiming to understand the process of crystal lattice stabilization, a combination of techniques was used, including X-ray diffraction (XRD), computational molecular modeling, and an ab initio molecular dynamic. The results show that α and β molecules are sterically barred from forming a direct hydrogen bond with one other. In addition, the presence of the methanol molecule stabilizes the crystal structure by a bifurcated O-H···O interaction acting as a bridge between them. The theoretical thermodynamic parameter and the rigid potential energy surface scan describe the role of methanol in the energy stabilization of the crystal. The absence of the methanol compound in the asymmetric unit destabilizes the crystalline structure, making the formation process of the asymmetric unit nonspontaneous. The energy difference between α and β molecules is around 0.80 kcal·mol(-1), indicating that both are stable and equally possible in the crystal lattice. The analysis of the energy profile of the C14-O2···H1-O3 and O2-H1···O3-C17 torsion angles in the crystal packing shows that the α and β molecules are confined in the stable potential region, in agreement with the two conformers in the asymmetric unit. The Molecular Electrostatic Potential (MEP) shows that the methanol has no steric effects, which prevents small motion around the torsion angles.

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m-Terphenyl-3,3″-dioxo-derived oxacalixaromatics: synthesis, structure, and solvent encapsulation in the solid state

Cited by 9 publications

References 58 publications

Single Step Synthesis of Acetylene-Substituted Oxacalix[4]arenes

Single Step Synthesis of Acetylene-Substituted Oxacalix[4]arenes

N1-(5-Fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine

Effect of the Methanol Molecule on the Stabilization of C₁₈H₁₈O₄ Crystal: Combined Theoretical and Structural Investigation

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m-Terphenyl-3,3″-dioxo-derived oxacalixaromatics: synthesis, structure, and solvent encapsulation in the solid state

Cited by 9 publications

References 58 publications

Single Step Synthesis of Acetylene-Substituted Oxacalix[4]arenes

Single Step Synthesis of Acetylene-Substituted Oxacalix[4]arenes

N1-(5-Fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine

Effect of the Methanol Molecule on the Stabilization of C18H18O4 Crystal: Combined Theoretical and Structural Investigation

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Effect of the Methanol Molecule on the Stabilization of C₁₈H₁₈O₄ Crystal: Combined Theoretical and Structural Investigation