Preparation and properties of isomeric N-(4-substituted benzylidene)-4-ethynylanilines and 4-substituted N-(4-ethynylbenzylidene)anilines

4-Substituted N-(4-ethynylbenzylidene)anilines (4-HC=C-C6H4-CH=N-C6H4-4-R; R = Me, t-Bu, OMe, F, Cl, Br, I, CF3 and NO2) have been prepared by condensation of 4-ethynylbenzaldehyde with appropriate anilines under mild conditions in good yields. The products obtained were fully characterized by GC-MS...

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Published inCollection of Czechoslovak chemical communications Vol. 65; no. 2; pp. 203 - 215
Main Authors Balcar, H, Cejka, J, Kubista, J, Petrusova, L, Kubat, P, Blechta
Format Journal Article
LanguageEnglish
Published PRAGUE 6 Inst Organic Chem And Biochem 2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
electronic spectroscopy
Schiff bases
polymerization
BASES
alkynes
SUBSTITUENTS
imines
N-BENZYLIDENEANILINES
ethynylated benzylideneanilines
C-13 CHEMICAL-SHIFTS
polyacetylenes
mass spectrometry
NMR spectroscopy
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Summary:4-Substituted N-(4-ethynylbenzylidene)anilines (4-HC=C-C6H4-CH=N-C6H4-4-R; R = Me, t-Bu, OMe, F, Cl, Br, I, CF3 and NO2) have been prepared by condensation of 4-ethynylbenzaldehyde with appropriate anilines under mild conditions in good yields. The products obtained were fully characterized by GC-MS, IR, NMR and UV-VIS spectroscopies and their properties were compared with a series of 4-ethynyl-N-(4-substituted benzylidene)anilines (4-HC=C-C6H4-N=CH-C6H4-4-R; R = H, Me, t-Bu, F, Br, NO2, CN, NMe2). The influence of substituent R on spectroscopic characteristics is discussed.
ISSN:0010-0765
DOI:10.1135/cccc20000203