US EPA

8715823 

Journal Article 

β-Hydroxy Carbonyl compounds via aldol reaction: Single crystal investigation and quantum chemical exploration for the unveiling of supramolecular behavior 

Khalid, M; Ali, A; Ud Din, Z; Tahir, MN; Morais, S; Braga, AAC; Akhtar, MN; Imran, M; Rodrigues-Filho, E 

2021 

Yes 

Journal of Molecular Structure
ISSN: 0022-2860
EISSN: 1872-8014 

1241 

English 

10.1016/j.molstruc.2021.130650 

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 P1¯ 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. 2021 Elsevier B.V. 

Aldol reaction; DFT investigation; Non-covalent interaction; Single crystal