title: UV photoelectron spectroscopic study of substituent effects in quinoline derivatives.
abstract: The molecular and electronic structure of eight substituted quinolines has been investigated by HeI/HeII photoelectron spectroscopy, Green's function calculations, and comparison with the spectra of related compounds. The correlation between nitrogen lone pair ionization energies and basicity in 18 substituted quinolines is discussed. The influence of different substituents has been quantified via the scheme that is based on experimental energy shifts. The relationships between nitrogen ionization energies, pK(a) values, and medicinal activity are also discussed.
authors.affiliation: Department of Chemistry and CPEC Centre, National University of Singapore, Singapore 117543, Singapore. chmigorn@nus.edu.sg
authors.forename: Igor
authors.initials: I
authors.lastname: Novak
authors.forename: Branka
authors.initials: B
authors.lastname: Kovac
mesh_terms: D000962:Antimalarials / Q000737:chemistry*; D004583:Electrons; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000962:Antimalarials; D011804:Quinolines; D009584:Nitrogen