title: Structure investigation of intramolecular hydrogen bond in some substituted salicylaldehydes and 4-aminoantipyrine derivatives in solution and in the solid state.
abstract: Seven imine derivatives obtained by condensation of appropriate aldehydes and salicylaldehydes with 4-aminoantipyrine were investigated in terms of intramolecular hydrogen bond structure. On the base of (1)H, (13)C and (15)N NMR measurements in solution and in the solid state we found out that all compounds which can form such structure exist as OH forms with strong H-bonds to nitrogen atom. The structure conclusions taken from NMR study were confirmed by pKa measurements. Surpassingly, the positions of protons in H-bridges only very slightly depend on the substituents in aldehyde used for condensation and on the phase (solution vs. solid state). The influence of antipyrine moiety seems to be the major factor defining H-bond structure.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, 44/52 Kasprzaka str., 01-224 Warsaw 42, POB 58, Poland. wojciech.schilf@icho.edu.pl
authors.forename: Wojciech
authors.initials: W
authors.lastname: Schilf
authors.forename: Bohdan
authors.initials: B
authors.lastname: Kamieński
authors.forename: Anna
authors.initials: A
authors.lastname: Szady-Chełmieniecka
authors.forename: Beata
authors.initials: B
authors.lastname: Kołodziej
authors.forename: Eugeniusz
authors.initials: E
authors.lastname: Grech
authors.forename: Dorota
authors.initials: D
authors.lastname: Zarzeczańska
authors.forename: Anna
authors.initials: A
authors.lastname: Wcisło
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Ossowski
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000675:Ampyrone / Q000031:analogs & derivatives*; D006860:Hydrogen Bonding; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D012545:Schiff Bases / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000447:Aldehydes; D012545:Schiff Bases; D000675:Ampyrone; C013243:salicylaldehyde