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Ab‐initio calculations of charge transfer interactions involving ascorbic acid and its metabolites
Author(s) -
Laurence Patricia R.,
Thomson Colin
Publication year - 1981
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.560200707
Subject(s) - ascorbic acid , chemistry , ab initio , methylglyoxal , ab initio quantum chemistry methods , formamide , computational chemistry , methylamine , electron transfer , molecule , dehydroascorbic acid , organic chemistry , food science , enzyme
Ascorbic acid enhances the free radical electron spin resonance signal obtained when methylamine interacts with methylglyoxal. Previous ab‐initio calculations have shown that methylglyoxal and other ketoaldehydes may act as possible electron acceptors in Szent‐Györgyi's theory of cancer. Ascorbic acid is also known to be involved in cancer. The ab‐initio SCF method has been used to study the electronic structure of ascorbic acid and its metabolites. The bulk of the calculations involved the use of α‐hydroxytetronic acid as a model for ascorbic acid, and related compounds as models for the ascorbyl radical and dehydroascorbic acid. Complete geometry optimizations by the force method were carried out for the model compounds, using an STO‐3 G basis set. To obtain an estimate of possible charge transfer involving these molecules, ab‐initio “supermolecule” calculations were carried out using formamide and glyoxal. A large number of planar and stacked orientations were considered The anion acts as a substantial donor in many of the stacked conformations, but the charge transfer is rather small in all these systems.