Comparison of Thermodynamic Hydrogen Bonding,Brönsted and Gas-phase Basicity with Spectroscopic Hydrogen Bonding Basicity of N 1,N 1 -Dimethylformamidines. Similarities and Differences in Substituent Effects †
Free accessResearch articleFirst published online February, 1999
Comparison of Thermodynamic Hydrogen Bonding,Brönsted and Gas-phase Basicity with Spectroscopic Hydrogen Bonding Basicity of N 1,N 1 -Dimethylformamidines. Similarities and Differences in Substituent Effects †
Comparison of the thermodynamic (logKHB with 4-fluorophenol in CCI4, pKa in azeotropic ethanol and GB in the gas phase) with spectroscopic basicities (ΔvOH of methanol in CCI4) for N1, N1-dimethylformamidines shows good correlation only between the pKa and ΔVOH values; no general simple linear model can be applied to the logKHB/ΔvOH and GB/ΔVOH relations.
References
1.
GalJ.-F., and MariaP.-C., Prog. Phys. Org. Chem., 1990, 17, 159.
2.
Similarity Models in Organic Chemistry, Biochemistry and Related Fields, ed. ZalewskiR. I., KrygowskiT. M., and ShorterJ., Elsevier, Amsterdam, 1991.
3.
LefflerJ. E., and GrunwaldE., Rates and Equilibria of Organic Reactions, Wiley, New York, 1963.
4.
TaftR. W., Prog. Phys. Org. Chem., 1983, 14, 247.
5.
RaczyńskaE. D., Pol. J. Chem., 1998, 72, 1215.
6.
RaczyńskaE. D., LaurenceC., and NicoletP., J. Chem. Soc., Perkin Trans. 2, 1988, 1491.
7.
RaczyńskaE. D., LaurenceC., and BerthelotM., Can. J. Chem., 1992, 70, 2203.
8.
OszczapowiczJ., and RaczyńskaE., Pol. J. Chem., 1983, 57, 419.
9.
RaczyńskaE. D., J. Chem. Res., 1991, (S) 90; (M) 763.
10.
DecouzonM., GalJ.-F., MariaP.-C., and RaczyńskaE. D., J. Org. Chem., 1991, 56, 3669.
11.
RaczyńskaE. D., MariaP.-C., GalJ.-F., and DecouzonM., J. Org. Chem., 1992, 57, 5730.
12.
TaftR. W., RaczyńskaE. D., MariaP.-C., LeitoI., GalJ.-F., DecouzonM., DrapałaT., and AnviaF., Pol. J. Chem., 1995, 69, 41.
13.
TaftR. W., and TopsomR. D., Prog. Phys. Org. Chem., 1987, 16, 1.
14.
HanschC., LeoA., and TaftR. W., Chem. Rev., 1991, 91, 165.
