Vibrational and electronic circular dichroism spectroscopies and DFT calculations for the assignment of the absolute configuration of hydroxy-substituted 2-tetralols

The abs. configuration of 1-and 2-tetralol (1a and 2a), of 5-hydroxy- and 8-hydroxy-2-tetralol (2b and 2c), and of 1-aminotetralin (1b) has been established by comparison of exptl. IR vibrational absorption (VA) and vibrational CD (VCD) spectra and d. functional theory (DFT) calcns. DFT calcns. using B3PW91 functional with TZ2P basis set were carried out to predict the VA and VCD spectra. Electronic CD (ECD) spectra were also measured and compared to time-dependent DFT calcns. The VCD data have been found to be more specific than ECD.