Crystal structures of selected hydroxymethyl and sulfanylmethylaryl derivatives

The crystal structures of eight compounds whose common features are an aromatic ring (naphthalene or benzene) and the presence of two hydroxymethyl groups or two sulfanylmethyl groups were examined. These are the isomers 1,2-, 1,3-, 1,5- and 1,7-bis(hydroxymethyl)naphthalene, C₁₂H₁₂O₂; 2,3-bis(hydroxymethyl)naphthalene, C₁₂H₁₂O₂; 2,3-bis(sulfanylmethyl)naphthalene, C₁₂H₁₂S₂; 1,2-bis(hydroxymethyl)benzene, C₈H₁₀O₂; and 1,2-bis(sulfanylmethyl)benzene, C₈H₁₀S₂. Different positions of the functional groups relative to each other are of fundamental importance in the way the molecules of these compounds are packed in the unit cells and have an impact on the interactions of the molecules of the compounds with each other. The changes that occur in the crystal structures when O atoms are replaced with S atoms in the functional groups are compared. A characteristic feature of the compounds studied is the lack of intramolecular hydrogen bonds between adjacent -OH or -SH groups.