Synthesis and characterization of 3-acetoxy-2-methyl-N-(phenyl)benzamide and 3-acetoxy-2-methyl-N-(4- methylphenyl)benzamide

• Published in: Journal of molecular structure 2018-01, Vol.1151, p.191-197
• Main Authors: Kırca, Başak Koşar, Çakmak, Şükriye, Kütük, Halil, Odabaşoğlu, Mustafa, Büyükgüngör, Orhan
• Format: Article
• Language: English
• Subjects: Amides; Crystal structure; NMR; XRD
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.09.034

This study treats about two successfully synthesized secondary amide compounds 3-Acetoxy-2-methyl-N-(phenyl)benzamide, I and 3-Acetoxy-2-methyl-N-(4-methylphenyl)benzamide, II. Compounds were characterized by FTIR, 1H NMR, 13C NMR and X-ray single crystal diffraction analysis techniques. Single crystal X-ray diffraction analyses show that while I crystallized in the orthorhombic system with space group Pbca, II crystallized in the triclinic system with space group P-1 and the asymmetric unit of II consists of two crystallographically independent molecules. Lattice constants are a = 7.9713 (3) Å, b = 9.5059 (3) Å, c = 37.1762 (2) Å, Z = 8 for I and a = 7.5579 (8) Å, b = 8.8601 (8) Å, c = 23.363 (3) Å, α = 97.011 (9) °, β = 96.932 (9)°, γ = 90.051 (8)°, Z = 4 for II. Crystallographic studies also show that the supramolecular structures were stabilized by intramolecular, intermolecular hydrogen bonds and CH … π interactions for both compounds. Characteristic amide bonds were observed in IR and NMR spectra. [Display omitted] •Two secondary amide compounds were synthesized.•Molecular structures were lightened with the single crystal XRD technique.•Intramolecular and intermolecular hydrogen bonds were analyzed.•Spectral behaviors of the compounds were analyzed with the FTIR and NMR studies.