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

Abstract

The absolute 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 experimental infrared vibrational absorption (VA) and vibrational circular dichroism (VCD) spectra and density functional theory (DFT) calculations. DFT calculations using B3PW91 functional with TZ2P basis set were carried out to predict the VA and VCD spectra. Electronic circular dichroism (ECD) spectra were also measured and compared to time-dependent DFT calculations. The VCD data have been found to be more specific than ECD.