Synthesis, spectroscopic studies, X-ray crystal structure and Hirshfeld surface analysis of unprecedented symmetrical trans-α,α′-bis(diphenylphosphoryl)cycloalkanol derivatives

A simple, efficient and high-yielding process has been developed for the synthesis of unprecedented symmetrical trans-alpha,alpha'-bis(diphenylphosphoryl)cycloalkanols (2a-d), through the p-toluenesulfonic acid-catalyzed reduction of trans-alpha,alpha'-bis(diphenylphosphoryl)cycloalkanones with sodium borohydride in ethanol at room temperature. The structures of the synthesized compounds were studied using various spectroscopic tools including IR, NMR (H-1, P-31, C-13) spectroscopy and mass spectrometry. The molecular structure of compound (2a) was further investigated using single crystal X-ray diffraction analysis. The Hirshfeld surface, curvedness, shape index and 2D-fingerprint plots were used to evaluate various intermolecular interactions within the crystal structure. UV-Vis and HOMO-LUMO properties of compound (2a) were also investigated. (C) 2019 Elsevier B.V. All rights reserved.