Substituent effects on the basicity of 3,7-diazabicyclo[3.3.1]nonanes.
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.
Toom
Lauri
L
Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, SE-75123, Uppsala, Sweden.
Kütt
Agnes
A
Kaljurand
Ivari
I
Leito
Ivo
I
Ottosson
Henrik
H
Grennberg
Helena
H
Gogoll
Adolf
A
D001372:Aza Compounds / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D001372:Aza Compounds; C011758:3,7-diazabicyclo(3.3.1)nonane