Abstract
Molecular structure of dipivaloylmethane was investigated by X-ray electron diffraction at 24°C. The C2v and Cs geometrical models involving an intramolecular hydrogen bond are considered. The C2v model with enol hydrogen lying symmetrically relative to the oxygen atoms has several advantages over the classical model of the enol tautomer.
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References
J. Emsley, J. Chem. Soc. Rev., 9, 91–124 (1980).
R. S. Haddon, J Am. Chem. Soc, 102, No. 6, 1807–1811 (1980).
S. F. Tayyari, Th. Zeegers-Huyskens, and J. L. Wood, Spedmchim. Ada, 35A, 1265–1275 (1979).
G. Gilli, F. Bellucci, V. Ferretti, and V. Bertolasi, J. Am. Chem. Soc, 111, 1023–1028 (1989).
S. L. Baugcum, R. W. Duerst, W. F. Rowe, et al., ibid., 103, 6296–6303 (1981).
A. H. Lowrey, C. George, P. D'Antonio, and J. Karle, ibid., 93, 6399–6403 (1971).
A. L. Andreassen and S. H. Bauer, J. Mol. Struct., 12, 381–403 (1972).
K. Iijima, A. Ohnogi, and S. Shibata, ibid., 156, 111–118 (1987).
A. L. Andreassen, D. Zebelman, and S. H. Bauer, J. Am. Chem. Soc, 93, 1148–1152 (1971).
E. Funke and R. Mecke, in: Hydrogen Bonding, D. Hadzi (ed.), Pergamon, London (1959), p. 433.
S. A. Shlykov and G. V. Girichev, Prib. Tekhn. Éksp., No. 2, 141-142 (1988).
V. I. Sokolov, N. I. Giricheva, and G. V. Girichev, Abstracts of Papers from the 9th International Young Researchers and Students' Conference on Chemistry and Chemical Engineering, Russian Chemical Engineering University, Moscow (1995), p. 70.
The Aldrich Library of Ft-IR Spectra, 2,2,6,6-Tetrumethyl-3,5-heptanedione, 1575-6.513A.
P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc, 116, 909–915 (1994).
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Translated from Zhumal Struktumoi Khimii, Vol. 41, No. 1, pp. 58-66, January–February, 2000
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Giricheva, N.I., Girichev, G.V., Lapshina, S.B. et al. Molecular structure of dipivaloylmethane and the intramolecular hydrogen bond problem. J Struct Chem 41, 48–54 (2000). https://doi.org/10.1007/BF02684727
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DOI: https://doi.org/10.1007/BF02684727