Structure of sp-9-hydroxy-9-pivaloylfluorene, product of base-catalyzed autoxidation of ap-9-pivaloylfluorene
| Autor: | J. L. Tunnell, Paul D. Robinson, Cal Y. Meyers, Duy H. Hua, S. Saha |
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| Rok vydání: | 1992 |
| Předmět: |
Fluorenes
Magnetic Resonance Spectroscopy Autoxidation Chemical Phenomena Molecular Structure Hydrogen bond Stereochemistry Chemistry Physical Molecular Conformation Hydrogen Bonding General Medicine Crystal structure Dihedral angle General Biochemistry Genetics and Molecular Biology Hydroxylation chemistry.chemical_compound Crystallography chemistry X-Ray Diffraction Intramolecular force X-ray crystallography Orthorhombic crystal system Crystallization Oxidation-Reduction |
| Zdroj: | Acta crystallographica. Section C, Crystal structure communications. 48 |
| ISSN: | 0108-2701 |
| Popis: | 1-(9-Hydroxyfluoren-9-yl)-2,2-dimethyl-1-propanone, C18H18O2, M(r) = 266.34, orthorhombic, Pbcn, a = 18.917 (10), b = 11.843 (8), c = 13.177 (7) A, V = 2952 (5) A3, Z = 8, Dx = 1.198 g cm-3, lambda(Mo K alpha) = 0.71069 A, mu = 0.72 cm-1, F(000) = 1136, T = 296 K, R = 0.044 for 1042 unique observed reflections. Conversion of ap-9-pivaloylfluorene, ap-(I), into lithiated (I)-9-anion followed by the addition of MeOH, then H2O, led to unexpected hydroxylation to provide 20-40% of sp-9-hydroxy-9-pivaloyfluorene, sp-(II), and 60-80% recovery of ap-(I). The singular sp conformation of (II) in solution suggested by NMR was confirmed in the crystalline state by X-ray diffraction which showed the O(1)-C(9)-C(10)-O(2) torsion angle approximately 0 degrees and the C(10) = O(2)...H(9)-O(1) non-bonding distance 1.95 (4) A, suggesting strong intramolecular hydrogen bonding in this conformation. |
| Databáze: | OpenAIRE |
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