Abstract
The strongly temperature-dependent1H-nmr spectrum of prop-1-en-1,2-diol-3-one (triosereductone), C3H4O3, can be explained on the basis of valency tautomerism. Intramolecular hydrogen bonding is responsible for this effect.
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References
Allan, E. A. & Reeves, L. W. (1962)J. Phys. Chem. 66, 613.
Allenstein, E. & Beyl, V. (1967)Chem. Ber. 100, 355.
Corio, P. L., Rutledge, R. L. & Zimmermann, J. R. (1958)J. Amer. Chem. Soc. 80, 3163.
Drinkard, W. C. & Kivelson, D. (1958)Z. Phys. Chem. 62, 1494.
Emsley, J. W., Feeney, J. & Sutcliffe, L. H.High Resolution Nuclear Magnetic Resonance Spectroscopy, (Pergamon, Oxford, 1965) Vol. 1, p. 534.
Euler, H. v. & Eistert, B.Chemie u. Biochemie der Reduktone und Reduktonate (F. Enke Verlag, Stuttgart, 1957, p. 53).
Frimmel, F., & Fritz, H. P. (1970)Z. Naturf. 24b, 57.
Hadzi, D. & Thompson, H. W.Hydrogen Bonding (Pergamon Press, London, 1959).
Jaffé, H. H. (1957)J. Amer. Chem. Soc. 79, 2373.
Lüttke, W. & Mecke, R. (1950)Z. Phys. Chem. 196, 56.
Owen, N. L. & Sheppard, N. (1963)Chem. Soc. (London), p. 264.
Piette, L. H. & Anderson, W. A. (1959)Z. Chem. Phys. 30, 899.
Pimentel, G. C. & McClellan, L. L.The Hydrogen Bond (Freeman, San Francisco, 1960).
Pople, J. A., Schneider, W. G. & Bernstein, H. J.High-Resolution Nuclear Magnetic Resonance (McGraw-Hill, New York, 1959, p. 400).
Rasmussen, G. S., Tunnicliff, D. D. & Brattain, R. R. (1949)J. Amer. Chem. Soc. 71, 1068.
Schneider, W. G., Bernstein, H. J. & Pople, J. A. (1958)J. Chem. Phys. 28, 601.
Shapet'ko, N. N. (1965)Tear. i. Eksperim. Khim. Akad. Nauk. Ukr. SSR,1 (4) 541.
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The helpful support of the ‘Deutsche Forschungsgemeinschaft’ is gratefully acknowledged.
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Frimmel, F., Fritz, H.P. & Kreiter, C.G. Valency tautomerism of triosereductone via hydrogen bonds. Journal of Crystal and Molecular Structure 1, 25–32 (1971). https://doi.org/10.1007/BF01200916
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DOI: https://doi.org/10.1007/BF01200916