Nature of the Sugar-Bisulfite Addition Compounds

Disagreement over whether the result of this addition reaction between aldehyde and bisulfite should be written as structure A or structure B continued for many decades  

Stelling (1928) found an absorption band in formaldehyde and acetone bisulfite addition compounds at 4992.0 A similar to that in sulfonic acids at 4992.2 and differing from that of metal alkyl (4996.0) and dialkyl sulfites (4997.7). He concluded from this that the sulfonic acid structure must be present. Raman spectral examinations of several aldehyde and ketone bisulfites by Caughlan and Tartar (1941) revealed the presence of a carbon-sulfur bond, possibly a carbon-hydroxyl bond, but no carbon doubly bonded to oxygen. This thus aided in discrediting both the tripartite molecule and the sulfurous acid ester structures. Sundman (1949) believes that formation of a stable monomolecular complex of boric acid and glucose bisulfite would be impossible if Schroeter s tripartite molecular structure were correct. His examinations of this complex led him to believe that its structure could be represented only by  

With deuterium as the aldehyde hydrogen in the molecule, Thompson and Cromwell (1939) found that p-phenylbenzaldehyde-di did not exchange aldehyde hydrogen with water but that the bisulfite addition compound did. This was interpreted as possibly indicating an enolization of the bisulfite addition compound  

Despite the continuing unquestioned fundamental merit of the research reported by Kerp, it rapidly became evident that his major contributions were in laying foundations onto which later investigators could anchor research plans it is interesting to contemplate the probable completeness of this early work if more modern concepts of reaction kinetics had been available. 

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