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Quantum mechanics studies of the tautomers of diacetylformoin, an important maillard product and odorant

Hattotuwagama, C.K., Drew, M.G.B. and Nursten, H.E. (2006) Quantum mechanics studies of the tautomers of diacetylformoin, an important maillard product and odorant. Journal of Molecular Structure-Theochem, 775 (1-3). pp. 67-76. ISSN 0166-1280

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To link to this item DOI: 10.1016/j.theochem.2006.08.014

Abstract/Summary

Diacetylformoin (3,4-dihydroxy-3-hexene-2,5-dione) has 16 tautomers, many with several possible conformations and all have been geometry optimised using quantum mechanics at the HF/6-31+G* level. Eleven structures have been identified with energies within 10 kcal mol(-1) of the minimum energy structure. Of these eight are acyclic and three cyclic. Calculations of NMR spectra have clarified the identity of the acyclic and cyclic structures found experimentally. The mechanism for cyclisation has been investigated and transition states obtained. The lowest energy reaction path requires the loss and gain of a proton during cyclisation. (c) 2006 Elsevier B.V. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Food and Nutritional Sciences
ID Code:13319
Uncontrolled Keywords:diacetylformoin, quantum mechanics, Maillard products, odorant, tautomeric structures, hydrogen bonding

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