Synthesis of new bis-bidendate N/O spiro-bino-spiro-cyclotriphosphazenes: Structural investigations and DFT studies


SÜZEN DEMİRCİOĞLU Y., METİNOĞLU S., Ashoor S. E.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.192, sa.1, ss.118-128, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 192 Sayı: 1
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1080/10426507.2016.1236103
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.118-128
  • Anahtar Kelimeler: N, O-donor type ligands, spiro-bino-spiro-cyclotriphosphazenes, spectroscopic techniques, single crystal X-ray crystallography, DFT, PHOSPHORUS-NITROGEN-COMPOUNDS, NUCLEOPHILIC-SUBSTITUTION REACTIONS, SCHIFF-BASE, CRYSTAL-STRUCTURES, DNA INTERACTIONS, SPECTRAL INVESTIGATIONS, BIOLOGICAL-ACTIVITIES, PHOSPHAZENE, DERIVATIVES, POLYPHOSPHAZENES
  • Anadolu Üniversitesi Adresli: Hayır

Özet

The Schiff bases 4,4'-di(2-hydroxybenzyl imino) diphenylmethane (S1), 4,4'-di(2-hydroxy-5-chloro benzyl imino) diphenylmethane (S2) and 4,4'-di(2-hydroxy-5-bromo benzyl imino) diphenylmethane (S3) were synthesized from the condensation reactions of salicyl-aldehyde, 5-chlorosalicylaldehyde and 5-bromosalicylaldehyde, respectively, with 4,4-diaminodiphenylmethane and reduced with NaBH4 in dry MeOH to obtain N/O-donor type ligands 4,4'-di(2-hydroxy benzyl amino) diphenylmethane (L1), 4,4'-di(2-hydroxy-5-chloro benzyl amino) diphenylmethane (L2) and 4,4'-di(2-hydroxy-5-bromo benzyl amino) diphenylmethane (L3). The novel spiro-bino-spiro-cyclotriphosphazene derivatives 1 - 3 were obtained from the reactions of L1-L3 with trimer (N3P3Cl6). The identities of these compounds were elucidated by P-31-, H-1-, C-13-NMR, FT-IR spectroscopy and elemental analysis. The solid state structures of compounds 1 and 2 were determined by single crystal X-ray diffraction. Experimental results on the molecular structures of compounds 1 and 2 were supported by computational studies using Density Functional Theory (DFT) methods with Becke-3-Lee-Yang-Parr (B3LYP) functional and 6-31+G(2d,p) basis set. The experimentally determined values of the bond angles and bond lengths in the compounds are in accord with to those predicted theoretically.