Two new benzamides: Synthesis, spectroscopic characterization, X-ray diffraction, and electronic structure analyses

Kirca B. K., ÇAKMAK Ş., Yakan H., ODABAŞOĞLU M., Buyukgungor O., Kütük H.

JOURNAL OF MOLECULAR STRUCTURE, vol.1203, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1203
  • Publication Date: 2020
  • Doi Number: 10.1016/j.molstruc.2019.127314
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Keywords: Secondary amides, Non-covalent interactions, Spectroscopic techniques, X-ray diffraction, Electronic structure, AMIDE-BOND, CARBOXYLIC-ACIDS, HOMO-LUMO, NMR, NLO, DFT, HYPERPOLARIZABILITY, PERFORMANCE, DERIVATIVES, NBO
  • Ondokuz Mayıs University Affiliated: Yes


This work includes the syntheses, molecular and electronic structure analyses of two novel secondary amide compounds 3-acetoxy-2-methyl-N-(2-methoxyphenyl)benzamide, 1 and 3-acetoxy-2-methyl-N-(3-methylphenyl)benzamide, 2. The title compounds were characterized by X-ray single crystal diffraction, FT-IR, H-1 NMR and (CNMR)-C-13-N- techniques and quantum chemical calculations were used for the investigations on electronic structure. X-ray diffraction analyses show that both compounds 1 and 2 crystallized in the triclinic system with space group P-1. While the characteristic amide bands were observed in IR and NMR spectra, crystallographic studies indicate that the supramolecular structures were stabilized by intramolecular and intermolecular hydrogen bonds and C-H center dot center dot center dot pi interactions for both compounds. Beside the experimental studies, natural bond orbital and molecular electrostatic potential analyses were carried out to understand the intramolecular charge transfers and hydrogen bonding behaviors of compounds. (C) 2019 Elsevier B.V. All rights reserved.