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

Author(s)

Khalid, Muhammad ^[1] ; Ali, Akbar ^[2] ; Din, Zia Ud ^[3] ; Tahir, Muhammad Nawaz ^[4] ; de Alcantara Morais, Sara Figueiredo ^[5] ; Carmo Braga, Ataualpa Albert ^[5] ; Akhtar, Muhammad Nadeem ^[6] ; Imran, Muhammad ^[7] ; Rodrigues-Filho, Edson ^[3]

Affiliation

^[1] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan

^[2] Govt Coll Univ Faisalabad, Dept Chem, Faisalabad - Pakistan

^[3] Univ Fed Sao Carlos, Dept Quim, LaBioMMi, CP 676, BR-13565905 Sao Carlos, SP - Brazil

^[4] Univ Sargodha, Dept Phys, Sargodha - Pakistan

^[5] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, Av Prof LineuPrestes 748, BR-05508000 Sao Paulo - Brazil

^[6] Islamia Univ Bahawalpur, Inst Chem, Div Inorgan Chem, Baghdad Ul Jadeed Campus, Bahawalpur 63100 - Pakistan

^[7] King Khalid Univ, Fac Sci, Dept Chem, POB 9004, Abha 61413 - Saudi Arabia

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1241, OCT 5 2021.
• Web of Science Citations: 0

Abstract

Aldol reaction is a carbon-carbon bond forming chemical reaction for synthesis of beta-hydroxy carbonyl compounds. In the current research work, we have synthesized beta-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 center dot center dot center dot O bonding together with N-O center dot center dot center dot pi interaction that further contribute to stabilization beside H-bonding interaction. Additionally, compound 1 is present in monoclinic crystal system with P2(1)/c space group while 2 is present in triclinic crystal system with P (1) over bar 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. (C) 2021 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
• Grantee: Ataualpa Albert Carmo Braga
• Support type: Regular Research Grants
• FAPESP's process: 11/07895-8 - Theoretical study of the Heck-Matsuda reactions
• Grantee: Ataualpa Albert Carmo Braga
• Support type: Scholarships in Brazil - Post-Doctorate
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support type: Research Projects - Thematic Grants