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Research on Chemical Intermediates

, Volume 35, Issue 5, pp 555–562 | Cite as

Study of cistrans stereochemistry of 2-(2-chlorobenzylideneamino)phenol and 2-(2-chlorophenyl imino)methyl)phenol (Schiff bases) by GC and GC-MS spectrometry

  • Hossein Fakhraian
  • Yaser Nafary
  • Hossein Chalabi
Article

Abstract

Cistrans stereochemistry of 2-(2-chlorobenzylideneamino)phenol (1) and 2-(2-chlorophenyl imino)methyl)phenol (2) (Schiff bases) was studied by GC-MS spectrometry, and cistrans conversion of the two compounds in solution was investigated by GC. Thus, 2 exists as a sole trans configuration and its conversion to cis was unsuccessful in any circumstance, while compound 1 exists as a mixture of two configurations in solution, occurrence of which were dependent on the temperature, heating time, solvent, and acid catalyst. X-ray crystallography of solid 1 presented a sole trans configuration.

Keywords

Cistrans stereochemistry Imine Schiff bases GC-MS spectrometry X-ray diffraction 

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Copyright information

© Springer Science+Business Media BV 2009

Authors and Affiliations

  • Hossein Fakhraian
    • 1
  • Yaser Nafary
    • 1
  • Hossein Chalabi
    • 1
  1. 1.Department of ChemistryImam Hossein UniversityTehranIran

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