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The crystal structures of two isomeric compounds, 2-endo-hydroxybornane-3-endo-carboxylic acid and 2 -exo -hydroxybomane-3 -endo-carboxylic acid, have been determined by X-ray single crystal analysis. The only difference between these two compounds is the disposition of the 2-hydroxy group with respect to the bomane skeleton. Both compounds show quite different hydrogen bonding schemes. In the endo-hydroxy-endo-carboxy isomer there is one intramolecular and one intermolecular hydrogen bond, which connects molecules into infinite chains, while in the exo-hydroxy-endo-carboxy isomer there are two intermolecular hydrogen bonds that form a more stable architecture of two kinds of chains which interconnect to close rings comprising four molecules. Due to these differences the melting point of 2 is ca. 30° higher than for 1 .

The Effect of Different Hydrogen Bonding Schemes on Melting Points of Two Isomeric 2-Hydroxy-bornane-3-carboxylic Acids