Biologically active 4-text-butyl-1-methyl-3,3,4,5,5-pentadeuterocyclohexane-1c,2c-diol and cis-2-phenyltetrahydropyran-5-ol have been prepared in the solid state, recrystallized and identified. Extensive measurements have been carried out on these materials comprising infrared; electronic absorption spectra before, and after exposure to an absorbed energetic, γ-ray dose (107rd). These materials were chosen as they have intramolecular hydrogen bonding of variant origin. The relative strength of hydrogen bonding and magnitude of γ-radiation damage were evaluated in each case. Results obtained were in conformity, explained, assigned and discussed in details in relation with the nature and origin of hydrogen bonding in each case.