Academic Journal
A combined experimental and theoretical study of the supramolecular self-assembly of the natural benzopyran 2,2-dimethyl-3-hydroxy-6-acetyl-chromane and its isomeric benzofuran 10,11-dihydro-10-hydroxytremetone
| العنوان: | A combined experimental and theoretical study of the supramolecular self-assembly of the natural benzopyran 2,2-dimethyl-3-hydroxy-6-acetyl-chromane and its isomeric benzofuran 10,11-dihydro-10-hydroxytremetone |
|---|---|
| المؤلفون: | Gil, Diego Mauricio, Lizarraga, Emilio Fernando, Echeverría, Gustavo Alberto, Piro, Oscar Enrique, Catalan, Cesar Atilio Nazareno, Ben Altabef, Aída |
| بيانات النشر: | Elsevier Science |
| المجموعة: | CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
| مصطلحات موضوعية: | BENZOFURAN DERIVATIVE, CHROMANE DERIVATIVE, CRYSTAL STRUCTURE, HYDROGEN BONDS, IR AND RAMAN SPECTROSCOPY, QUANTUM CHEMICAL CALCULATIONS, https://purl.org/becyt/ford/1.4, https://purl.org/becyt/ford/1 |
| الوصف: | Epoxidation of 4HMBA, the main metabolite of the medicinal plant Sencecionutans, produces an unstable epoxide eventually giving rise to a mixture of four derivatives, three of them previously reported as natural products. The epoxide product easily undergoes an intra-molecular attack of the phenolic hydroxyl against the epoxide group carbons to produce either a benzofuran or a chromane derivative. When dissolved in methanol-water mixture at room temperature the epoxide is completely solvolyzed to give the corresponding diol (hydrolysis) or vicinal hydroxyl-methoxy (methanolysis) derivative. All the compounds involved in the above reactions were characterized by IR, Raman, H NMR and UV–vis spectroscopies, and by mass spectrometry. Density functional theory (DFT) computations were used to optimize the structure conformations. The optimized structures were further subjected to a Natural Bond Orbital (NBO) and electrostatic potentials analysis. The crystal structures of the title compounds (for short, 3 and 4 respectively) were determined by X-ray diffraction methods. Compound 3 crystallizes in the triclinic P-1 space group with a = 6.4289 (6) Å, b = 8.7120 (6) Å, c = 10.952 (1) Å, α = 92.280 (7)°, β = 95.738 (7)°, γ = 103.973 (7)°, and Z = 2 molecules per unit cell and 4 in the monoclinic P21/c space group with a = 11.2891 (6) Å, b = 9.1902 (4) Å, c = 12.4272 (7) Å. Β = 113.689 (7)°, and Z = 4. In 3 neighboring molecules are linked to each other by OH⋯O (keto) bonds giving rise to a polymeric structure. In 4 the OH group is a bifurcate H-bond donor. It forms a weak intra-molecular OH⋯O (furan) bond and also a much stronger inter-molecular O[sbnd]H⋯O (keto) bond giving rise to a zig-zag polymeric structure. A detailed analysis of the solid state molecular interactions of compounds 3 and 4 has been performed using Hirshfeld surface analysis and their associated 2D fingerprint plots. ; Fil: Gil, Diego Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. ... |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | English |
| تدمد: | 0022-2860 |
| Relation: | info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286017307573; http://hdl.handle.net/11336/50179; Gil, Diego Mauricio; Lizarraga, Emilio Fernando; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Catalan, Cesar Atilio Nazareno; et al.; A combined experimental and theoretical study of the supramolecular self-assembly of the natural benzopyran 2,2-dimethyl-3-hydroxy-6-acetyl-chromane and its isomeric benzofuran 10,11-dihydro-10-hydroxytremetone; Elsevier Science; Journal of Molecular Structure; 1146; 10-2017; 164-178; CONICET Digital; CONICET |
| الاتاحة: | http://hdl.handle.net/11336/50179 |
| Rights: | info:eu-repo/semantics/restrictedAccess ; https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
| رقم الانضمام: | edsbas.34533908 |
| قاعدة البيانات: | BASE |
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