Structural, spectroscopic, and theoretical investigations of (E)-methyl-3-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-4-methylbenzoate

Bingol Alpaslan Y., GÖKCE H., Macit M., Kaya S., ALPASLAN G.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol.68, no.6, pp.989-1001, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 68 Issue: 6
  • Publication Date: 2021
  • Doi Number: 10.1002/jccs.202000285
  • Journal Name: JOURNAL OF THE CHINESE CHEMICAL SOCIETY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, CAB Abstracts, Chemical Abstracts Core, INSPEC
  • Page Numbers: pp.989-1001
  • Keywords: electronic properties, Hirshfeld surface analysis, molecular modeling, spectroscopy, DENSITY-FUNCTIONAL THEORY, SCHIFF-BASE COMPLEXES, DFT CALCULATIONS, HIRSHFELD SURFACES, BIOLOGICAL-ACTIVITY, CRYSTAL-STRUCTURE, SOLID-STATE, ANTIBACTERIAL, COPPER(II), NICKEL(II)
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

A novel Schiff base ((E)-methyl-3-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-4-methylbenzoate (MDM), C24H31NO3) at phenol-imine form with the O-HMIDLINE HORIZONTAL ELLIPSISN intra-molecular hydrogen bond was synthesized. Its structural and spectroscopic characterizations were performed by using experimental (single crystal X-ray diffraction, Fourier transform infrared [FT-IR], NMR chemical shift, and UV-vis spectroscopies) and theoretical (DFT/B3LYP/6-311+G[2d,p] computational level) methods. X-ray diffraction investigation shows that the MDM crystallized in phenol-imine form with O-HMIDLINE HORIZONTAL ELLIPSISN intra-molecular hydrogen bond. Detailed investigations of the presence and nature of the inter-molecular contacts within solid state crystal packing form of MDM were examined by Hirshfeld surface analysis. The intra-molecular electronic transitions in the compound were investigated and determined by UV-vis electronic absorption wavelengths and FMOs analyses. The structural, vibrational, and NMR chemical shift analyses of azomethine (-CH(sic)N-) and phenolic hydroxyl (-OH) groups in MDM supported its phenol-imine structural formation.