title: Substituent effects on the basicity of 3,7-diazabicyclo[3.3.1]nonanes.
abstract: Basicity constants for a series of 3,7-diazabicyclo[3.3.1]nonane derivatives in acetonitrile with a variation over 13 orders of magnitude have been determined using a spectrophotometric titration technique. An excellent correlation between basicity and calculated proton affinities obtained at PCM-B3LYP/6-31+G(d)//B3LYP/6-31G(d) level was found. The results are discussed in terms of substituent effects and compared to (15)N NMR chemical shifts.
authors.affiliation: Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, SE-75123, Uppsala, Sweden.
authors.forename: Lauri
authors.initials: L
authors.lastname: Toom
authors.forename: Agnes
authors.initials: A
authors.lastname: Kütt
authors.forename: Ivari
authors.initials: I
authors.lastname: Kaljurand
authors.forename: Ivo
authors.initials: I
authors.lastname: Leito
authors.forename: Henrik
authors.initials: H
authors.lastname: Ottosson
authors.forename: Helena
authors.initials: H
authors.lastname: Grennberg
authors.forename: Adolf
authors.initials: A
authors.lastname: Gogoll
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D001372:Aza Compounds; C011758:3,7-diazabicyclo(3.3.1)nonane