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Journal Article 
Synthesis and Crystal Structure of trans-2,8-Dihydroxy-l(7)-p-menthene, a New Terpenoid Diol1 
Scott, WE; Richards, GF 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
The crystal structure of a new terpenoid diol, trans-2,8-dihydroxy-l(7)-p-menthene, has been determined from three-dimensional X-ray data obtained near the temperature of liquid nitrogen. The structure was solved by application of the symbolic addition method for noncentrosymmetric crystals. It refined to an R index of 0.083. The methylenecyclohexane ring took on the ordinary chair conformation with the ring hydroxyl group axial and the 2-hydroxyisopropyl group equatorial. As indicated by the dihedral angles, 45.5 and 52.6°, the ring is flatter than that of cyclohexane. The molecules are held together in the crystal by a network of hydrogen bonds in which each hydroxyl participates in linkages with two other molecules. 1971, American Chemical Society. All rights reserved.