Rules to Describe Hydrogen-Bonding Patterns in Monosaccharides

For the pyranoses and pyranosides, a relatively large number of high precision X-ray and neutron diffraction results are available. Both a metrical analysis [58] and a pattern recognition analysis [59] were carried out based on a combination of neutron and normalized X-ray structure data. The results of the metrical analysis of the 0H---0 hydrogen-bond geometry are described in Part IB, Chapters 6 and 7. 

3 Rules to Describe Hydrogen-Bonding Patterns in Monosaccharides 

Make use of the cooperative effect, by forming as many infinite chains as possible, as in the alditol crystal structures. 

Clearly, there is an inconsistency between these two rules, because hydrogen-bond chains must necessarily terminate when they include ring or glycosidic oxygens. 

These rules permitted the known monosaccharide crystal structures to be classified into four different hydrogen-bonding schemes. On the basis of these three rules, it was found that the 44 crystal structures for which neutron or good X-ray data were available at the time of the analysis, could be divided into four classes, which are shown in Thble 13.2. 

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