Structural information from OH stretching frequencies - VI. On the presence of different rotamers in alkyl substituted tertiary adamantanol-2 and bicyclononanol-9 compounds

Article abstract of DOI:10.1016/0584-8539(81)80099-2

The presence of different hydroxyl rotamers in alkyl substituted tertiary adamantanol-2 and bicyclo<3.3.1>nonanol-9 compounds has been studied in CCl4 solution by means of the i.r. absorption of the OH-stretching band.The rotamer with the OH positioned over the ring skeleton proves to be sensitive to the alkyl substituent.Furthermore it is found that the adamantanol compounds behave differently from the corresponding cyclohexanol derivatives.It is demonstrated that information regarding the special orientation of the alkyl substituent can be derived from the OH-band.