Physical properties of some common organic solvents


 

  α β ε μ Y Z ET
Acetic Acid 1.12 6.2 1.74 -1.639 79.2 51.7
Water 1.17 0.14 84.2  2.2  3.49  94.6  63.1
Formamide 110  3.7  0.6  83.2  56.6 
Methanol 0.93 0.62 38.6  3.46  -1.09  83.6  55.5 
Ethanol/water(80%) 36    0  84.8  53.6 
Ethanol 0.83 0.77 24.3  1.69  -2.03  79.6  51.9 
Isopropyl alcohol 0.76 0.92 18.3  1.66  -2.73  76.3  48.6 
Acetonitrile 36.2  3.92    71.3  46 
Dimethylsulfoxide 0.743 49  3.96    71.1  45 
Sulfolane 44  4.7    77.5  44 
t-Butanol 0.68 0.95 10.9  1.66  -3.26  71.3  43.9 
Dimethylformamide 0.707 36.7  3.86    68.5  43.8 
Acetone 0.507 20.7  2.88    65.7  42.2 
Dichloromethane 8.9  1.6    64.2  41.1 
Pyridine 0.668 12.3  2.19    64  40.2 
Chloroform 4.7  1.87    63.2  39.1 
Hexamethylphosphoramide 1.00 30  5.54    62.8  40.9 
Tetrahydrofuran 0.553 7.32  1.63      37.4 
Diethyl ether 0.514 4.34  1.15      34.6 
Benzene 2.28  0    54  34.5 
Toluene 2.38  0.36      33.9 
Carbon tetrachloride 2.23  0      32.5 
Hexane 1.89  0.08      30.9 

Definitions:

α = describes the ability of a solvent to donate a proton in a solvent-to-solute hydrogen bond. Ref: Murray & Politzer, J. Org., Chem., 1991, 56, 6715-6717.

β = describes the ability of a solvent to accept a proton in a solute-to-solvent hydrogen bond. Ref: Taft et al., J. Am. Chem. Soc., 1976, 98, 377-383.

ε = dielectric constant, a macroscopic property of the solvent as a continuous medium. Ref: Wikipedia.

μ = dipole moment, debyes, a microscopic property of the individual molecule. Ref: Wikipedia.

Y = log(k(test solvent)/k(80%EtOH/water)) for SN1 reaction of tert-butyl chloride at 25°C. A more polar solvent makes this reaction faster, and Y more positive. Ref: J. Am. Chem. Soc., 1948, 70, 846-854.

Z = energy of the photochemical excitation of methyl N-ethyl-4-pyridinecarboxylate iodide, kcal/mol, in the particular solvent. Ref: E. M. Kosower, An Introduction to Physical Organic Chemistry (Wiley, New York, 1968).

ET = energy of the photochemical excitation of an N-phenoxypryidinium zwitterion, kcal/mol, in the particular solvent. Ref: Reichardt, Chem. Rev., 1994, 94, 2319-2358.

For both Z and ET, the stabilization of the polar reactant vs. the nonpolar excited state leads to an increase in excitation energy in polar solvents.

Solvent Properties

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02/28/05 ;