Efficient Synthesis of Imine-Carboxylic Acid Functionalized Compounds: Single Crystal, Hirshfeld Surface and Quantum Chemical Exploration

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 7; p. 2967
• Main Authors: Tahir, Muhammad Nawaz, Ali, Akbar, Khalid, Muhammad, Ashfaq, Muhammad, Naveed, Mubashir, Murtaza, Shahzad, Shafiq, Iqra, Asghar, Muhammad Adnan, Orfali, Raha, Perveen, Shagufta
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 27.03.2023; MDPI
• Subjects: Acids; Analysis; Bonding strength; Carboxylic acids; Charge transfer; Chemistry; Comparative analysis; condensation reaction; Density functional theory; Electrostatic properties; Hirshfeld surface analysis; Imines; Ligands; Molecular orbitals; Molecular structure; NBO analysis; para-Aminobenzoic acid; Schiff bases; Single crystals; single-crystal XRD; Structural stability; Surface analysis (chemical); X-ray diffraction; Pakistan; condensation reaction; Hirshfeld surface analysis; single-crystal XRD; density functional theory; NBO analysis
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28072967

Two aminobenzoic acid based crystalline imines ( and ) were synthesized through a condensation reaction of 4-aminobenzoic acid and substituted benzaldehydes. Single-crystal X-ray diffraction was employed for the determination of structures of prepared Schiff bases. The stability of super molecular structures of both molecules was achieved by intramolecular H-bonding accompanied by strong, as well as comparatively weak, intermolecular attractive forces. The comparative analysis of the non-covalent forces in and was performed by Hirshfeld surface analysis and an interaction energy study between the molecular pairs. Along with the synthesis, quantum chemical calculations were also accomplished at M06/6-311G (d, p) functional of density functional theory (DFT). The frontier molecular orbitals (FMOs), molecular electrostatic potential (MEP), natural bond orbitals (NBOs), global reactivity parameters (GRPs) and natural population (NPA) analyses were also carried out. The findings of FMOs found that for was examined to be smaller (3.477 eV) than that of (3.7933 eV), which indicated a greater charge transference rate in . Further, the NBO analysis showed the efficient intramolecular charge transfer (ICT), as studied by Hirshfeld surface analysis.