β-Hydroxy Carbonyl Compounds Via Aldol Reaction: Single Crystal Investigation and Quantum Chemical Exploration for the Unveiling of Supramolecular Behavior

Abstract Aldol reaction is a carbon-carbon bond forming chemical reaction for synthesis of β-hydroxy carbonyl compounds. In the current research work, we have synthesizedβ-hydroxy carbonyl compounds i.e 2-(hydroxy(4-nitrophenyl)methyl)cyclohexan-1-one (1) 2-(hydroxy(o-tolyl)methyl)cyclohexan-1-one (2) using base mediated aldol reaction. The chemical structures of the synthesized compounds have been analyzed by the single crystal investigation. The SC-XRD data reveals that intermolecular forces are responsible for crystals stabilization. These compounds are linked together in the form of dimers that are interlinked through C-H…O bonding together with N-O…π interaction that further contribute to stabilization beside H-bonding interaction. Additionally, compound 1 is present in monoclinic crystal system with P21/c space group while 2 is present in triclinic crystal system with P 1 ¯ space group. Moreover, DFT calculations were performed with B3LYP-D3/6-311G(d,p) method to calculate non-covalent interactions in compounds 1 and 2 through NBO and AIM analysis. TD-DFT computations with CAM-B3LYP/6-311G(d,p) level of theory were also performed to evaluate the reactivity of compounds 1 and 2 through FMO, GRD and hole-electron analysis. Theoretical calculations demonstrate the importance of substituent groups on the reactivity and their influence in the non-covalent interactions which direct their arrangement.