Similarities and differences between azomethines and ketimines: synthesis, materials characterization and structure of novel imines compounds.
Imines (ketimines and azomethines) derived from p-dibenzoylbenzene (DB) and terephthalic aldehyde (TA) and two aromatic amines: aniline and 2,6-dimethylaniline have been investigated. Compounds were synthesized via condensation of amines with carbonyl monomers in DMA or amine solution. When using DMA as a solvent, azomethines with high yields were obtained. On the other hand, the amines used as a monomers served also as an effective solvent for the synthesis of the ketanils. This different reactivity of the aldehyde and ketone groups in DMA and in amine depends on the dehydration mechanism being dominated by a kinetic process or thermodynamic one. On the basis of FTIR, 13C and 1H NMR, UV-vis spectra, thermal characteristic and theoretical calculations conclusions are drawn regarding the similarities and differences between azomethines and ketimines.
Iwan
Agnieszka
A
Centre of Polymer Chemistry, Polish Academy of Sciences, 34 M. Curie-Sklodowska Street, 41-819 Zabrze, Poland. aiwan@cchp-pan.zabrze.pl
Kaczmarczyk
Bozena
B
Janeczek
Henryk
H
Sek
Danuta
D
Ostrowski
Slawomir
S
D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D001391:Azo Compounds / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D002152:Calorimetry, Differential Scanning; D003408:Cresols / Q000737:chemistry; D007097:Imines / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D012996:Solutions; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics; D013882:Thiosemicarbazones / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D044366:Transition Temperature
D001391:Azo Compounds; D003408:Cresols; D007097:Imines; D012996:Solutions; D013882:Thiosemicarbazones; C512188:azomethine; C042294:N,N-dimethylalanine; C042041:3-cresol; D000409:Alanine