Collect. Czech. Chem. Commun. 2000, 65, 203-215

Preparation and Properties of Isomeric N-(4-Substituted Benzylidene)-4-ethynylanilines and 4-Substituted N-(4-Ethynylbenzylidene)anilines

Hynek Balcara,*, Jiří Čejkaa, Jiří Kubištaa, Lidmila Petrusováa, Pavel Kubáta and Vratislav Blechtab

a J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, 182 23 Prague 8, Czech Republic
b Institute of Chemical Process Fundamentals, Academy of Sciences of the Czech Republic, 165 02 Prague 6-Suchdol, Czech Republic


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.

Keywords: Alkynes; Schiff bases; Imines; Ethynylated benzylideneanilines; Polyacetylenes; Polymerization; Mass spectrometry; NMR spectroscopy; Electronic spectroscopy.

References: 20 live references.