Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride

ÇAKMAK Ş., Kansiz S., Azam M., VEYİSOĞLU A., Yakan H., Min K.

ACS OMEGA, vol.7, no.20, pp.17192-17201, 2022 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 20
  • Publication Date: 2022
  • Doi Number: 10.1021/acsomega.2c00879
  • Journal Name: ACS OMEGA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Directory of Open Access Journals
  • Page Numbers: pp.17192-17201
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

We report a novel anhydride derivative, 3-acetoxy-2-methylbenzoic anhydride (AMA), obtained from the interaction of 3-acetoxy-2-methylbenzoyl chloride with 3-acetoxy-2-methylbenzoic acid. The synthesized compound was characterized by elemental analysis, IR, H-1 NMR, and C-13 NMR spectroscopic studies and single-crystal X-ray crystallography which revealed the crystallization of AMA as monoclinic with space group P2(1)/c. A Hirshfeld surface analysis was performed to record various intermolecular interactions, indicating the stabilization of the AMA structure by the intermolecular weak C-H center dot center dot center dot O hydrogen bonds and pi center dot center dot center dot pi interactions. The title compound was screened for antibacterial and antifungal activities using a serial dilution technique under aseptic conditions. The results indicate that the title compound has significant antibacterial properties but showed no antifungal behavior.