Crystal structure and DFT computational studies of (E)-2,4-di-tert-butyl-6-{[3-(trifluoromethyl)benzyl]-iminomethyl}phenol

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Kaynar N. K., TANAK H., Macit M., Özdemir N.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.732-741, 2020 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1107/s205698902000537x
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.732-741
  • Anahtar Kelimeler: Schiff base, rotational disorder, enol-imine, tert-butyl, DFT, crystal structure
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The title compound, C23H28F3NO, is an ortho-hydroxy Schiff base compound, which adopts the enol-imine tautomeric form in the solid state. The molecular structure is not planar and the dihedral angle between the planes of the aromatic rings is 85.52 (10)degrees. The trifluoromethyl group shows rotational disorder over two sites, with occupancies of 0.798 (6) and 0.202 (6). An intramolecular O-H center dot center dot center dot N hydrogen bonding generates an S(6) ring motif. The crystal structure is consolidated by C-H center dot center dot center dot pi interactions. The molecular structure was optimized via density functional theory (DFT) methods with the B3LYP functional and LanL2DZ basis set. The theoretical structure is in good agreement with the experimental data. The frontier orbitals and molecular electrostatic potential map were also examined by DFT computations.