Synthesis, infra red and nmr intensities of amphiphilic adamantane derivatives: Impact of hydroxylation, acetylation and chlorination

Novel chloro substituted adamantanamide was designed to have better supramolecular sites and accordingly synthesized via hydroxylation, acetylation and chlorination. Due to the specific electronic properties of chlorine atom it imparts better applications. Functionalization of highly unreactive adamantane was achieved with an overall yield of 80% under milder reaction conditions. Hydroxylation of adamantamine was carried out using urea as catalyst (10mol%) with an yield of 97%. Acetylation was optimized using acylating reagent (acetyl chloride, 1.1 equivalents) and DIPEA (1.5 equivalents) which resulted 97% yield. Finally, chlorination was carried out with thionyl chloride (2.0 equivalents) at 65 degrees C (84% yield). IR and NMR (including D2O exchanded) spectra were analyzed along with ESI-MS data of all the products. DFT studies were carried using B3LYP level {6-311++G (d, p) basis set}out for all the products to predict the stability, reactivity and other global descriptors.