Hypervalent and binuclear silicon and germanium derivatives from bis-(3,5-di-tert-butyl-2-phenol)-oxamide |
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Authors: | Víctor M Jiménez-Pérez Ángel Ramos-Organillo Adrián Peña-Hueso Angelina Flores-Parra |
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Institution: | a Departamento de Química, Cinvestav, A.P. 14-740, C.P. 07000, México, D.F., Mexico b Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana, Xochimilco, Calzada del Hueso 1100, Colonia Villa Quietud, C.P. 04960 México, D.F., Mexico c Facultad de Ciencias Químicas, Universidad de Colima, A.P. 28400, Coquimatlán, Colima, Mexico |
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Abstract: | The reactions of bis-(3,5-di-tert-butyl-2-phenol)oxamide (1) with Cl2SiR2 (Me or Ph) or Cl2GeR2 (Me, nBu or Ph) in THF provided binuclear pentacoordinated silicon and germanium compounds: bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-dimethylsilane (2), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-diphenylsilane (3), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-dimethylgermane (4), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-di-n-butylgermane (5) and bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-diphenylgermane (6). The mono-nuclear tetracoordinated silicon compounds N-acetyl-bis-(3,5-di-tert-butyl-2-oxo-phenyl)-amide-bis-(dimethylsilane) (8) and N-acetyl-bis-(3,5-di-tert-butyl-2-oxo-phenyl)-amide-bis-(diphenylsilane) (9) were synthesized from N-(3,5-di-tert-butyl-2-phenol)acetamide (7) and Cl2SiR2 (R = Me and Ph). Comparison of the 29Si NMR chemical shifts of the penta- (2 and 3) and tetracoordinated (8 and 9) silicon compounds provided information about the intramolecular coordination of the carbonyl group to the silicon atom. Compounds 3 and 6 were characterized by single-crystal X-ray analyses. They have planar hexacyclic structures where the central atoms present distorted tbp geometries with one nitrogen and two carbon atoms in equatorial positions and two oxygen atoms in apical positions. |
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Keywords: | Organosilane Organogermane X-ray structures 29Si NMR Aromatic hexacycles |
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