Synthesis, IR, UV/vis-, (1)H NMR and DFT study of chelatophore functionalized 1,3-benzoxazinone spiropyrans

Spectrochim Acta A Mol Biomol Spectrosc. 2008 Dec 1;71(3):1146-52. doi: 10.1016/j.saa.2008.03.014. Epub 2008 Mar 25.

Abstract

Six novel functionalized spiropyran's derivatives of 2H-1,3-benzoxazinone series were synthesized by introducing the substituents with chelating ability into 2H-chromene part of the 8'-formyl-7'-hydroxy-3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazine-2-spiro-2'-[2H]-chromene (I) by condensation with 2-aminophenol, 2-amino-4-methylphenol, 2-amino-4-nitrophenol, 2-amino-1-methylbenzimidazole, 4-amino-4H-1,2,4-triazole, N-(4-aminophenyl)acetamide. (1)H NMR, UV/vis, IR spectroscopy combined with quantum-chemical calculations employing density functional theory (DFT) were used to study their structure. All substances, except 2-amino-4-nitrophenol derivative exist in solid state and in solution solely in closed spiroform, while the mentioned one undergoes partial spiropyran ring opening. In DMSO solution NMR spectra show ratio of 2:1 of closed and opened form, correspondingly.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry*
  • Chelating Agents / chemical synthesis
  • Chelating Agents / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry*
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry*
  • Quantum Theory
  • Spectrophotometry
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Thermodynamics

Substances

  • Benzopyrans
  • Chelating Agents
  • Indoles
  • Nitro Compounds
  • Oxazines
  • spiropyran