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The relative stability of the tautomers of α‐Hydroxytetronic acid
Author(s) -
Bäucker Thomas,
Klessinger Martin,
EckertMaksić Mirjana,
Maksić Zvonimir B.
Publication year - 1994
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560500602
Subject(s) - tautomer , chemistry , intramolecular force , hydrogen bond , ascorbic acid , computational chemistry , gas phase , hydrogen , crystallography , stereochemistry , molecule , organic chemistry , food science
The relative stability of the four tautomeric forms of α‐hydroxytetronic acid was calculated with full geometry optimization at the STO ‐3 G , 3–21 G , 6–31 G *, and 6–31 G ** SCF levels. Correlation effects were estimated using the MP 2 method. Intramolecular hydrogen bonds are found to be of primary importance for the relative stability of the various tautomers, and the same tautomer that in the case of L ‐ascorbic acid is experimentally observed in the crystal as well as in solution is found to be the most stable one, if polarization functions on the hydrogen atoms are taken into account. It is concluded that even in the gas phase this tautomer predominates in α‐hydroxytetronic acid as well as in L ‐ascorbic acid. © 1994 John Wiley & Sons, Inc.