Why is acetonitrile more polar than acetaldehyde

Solvent Polarity Index Dipole moment Dielectric Constant Boiling Point Freezing Point
Pentane 0.0 0 1.84 36.1 -129.7
Cyclopentane 0.1 0 1.97 49.3 -93.9
Heptane 0.1 0 1.92 98.4 -90.6
Hexane 0.1 0.08 1.88 68.7 -95.3
Cyclohexane 0.2 0 2.02 80.7 6.5
Toluene 2.4 0.31 2.38 110.6 -94.5
o-Xylene 2.5 0.45 2.57 144.4 -25.2
Chlorobenzene 2.7 1.54 5.62 131.7 -45.6
o-Dichlorobenzene 2.7 2.14 9.93 180.5 -17.0
Diethyl Ether 2.8 1.15 4.33 34.5 -117.4
Dichloromethane 3.1 1.14 8.93 39.7 -95.1
1,2-Dichloroethane 3.5 1.83 10.36 83.5 -35.7
Isopropyl Alcohol 3.9 1.66 19.92 82.3 -88.0
n-Butyl Acetate 4.0 1.84 5.01 126.1 -73.5
n-Propyl Alcohol 4.0 3.09 20.33 97.2 -126.2
Ethyl Alcohol - 1.66 24.55 78.3 -114.1
Glyme - 1.71 7.20 84.5 -69
Tetrahydrofuran 4.0 1.75 7.58 66 -108.5
Chloroform 4.1 1.15 4.81 61.1 -63.5
Ethyl Acetate 4.4 1.88 6.02 77.1 -84.0
Ethyl Methyl Ketone 4.7 2.76 18.51 79.6 -86.7
1,4-Dioxane 4.8 0.45 2.25 101.3 11.8
Acetone 5.1 2.69 20.7 56.3 -94.7
Methanol 5.1 2.87 32.70 64.7 -97.7
Pyridine 5.3 2.37 12.4 115.2 -41.5
2-MethoxyEthanol 5.5 2.04 16.93 124.6 -85.1
Acetonitrile 5.8 3.44 37.5 81.6 -43.8
N,N-DimethylFormamide 6.4 3.86 36.71 153.0 -60.4
DimethylAcetamide 6.5 3.72 37.78 166.1 -20
N-MethylPyrrolidone 6.7 4.09 32.2 202 -24.4
Dimethyl Sulfoxide 7.2 4.1 46.68 189 18.5
Water 10.2 1.87 80.1 100.0 0.0

Values Taken from http://www.bandj.com/BJProduct/SolProperties/Polarity.html
For reference and additional solvents follow this Link. Compiled by A.Chandrasekaran

 

Properties of Organic Solvents

The values in the table below except as noted have been extracted from online and hardbound compilations . Values for relative polarity, eluant strength, threshold limits and vapor pressure have been extracted from: Christian Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH Publishers, 3rd ed., 2003.  http://www.knovel.com/web/portal/browse/display?_EXT_KNOVEL_DISPLAY_bookid=761 
http://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp 
The tables below were posted (10/23/98) and revised (07/28/09) and updated (04/10/10) by Steve Murov, Professor Emeritus of Chemistry.

 Table 1 arranged alphabetically, Table 2 arranged according to increasing polarity

TABLE 1

Solvent formula boiling point (oC) melting point (oC)  density 
(g/mL)
solubility in H2O1  (g/100g) relative
polarity2
eluant strength3 threshold limits4 (ppm) vapor pressure 20oC (hPa)
acetic acid C2H4O2 118 16.6 1.049 M 0.648 >1 10 15.3
acetone C3H6O 56.2 -94.3 0.786 M 0.355 0.56 500 240
acetonitrile C2H3N 81.6 -46 0.786 M 0.460 0.65 20 97
acetyl acetone C5H8O2 140.4 -23 0.975 16 0.571      
2-aminoethanol C2H7NO 170.9 10.5 1.018 M 0.651   3 0.53
aniline C6H7N 184.4 -6.0 1.022 3.4 0.420   2 0.4
anisole C7H8O 153.7 -37.5 0.996 0.10 0.198      
benzene C6H6 80.1 5.5 0.879 0.18 0.111 0.32 0.5 101
benzonitrile C7H5N 205 -13 0.996 0.2 0.333   10 12
benzyl alcohol C7H8O 205.4 -15.3 1.042 3.5 0.608      
1-butanol C4H10O 117.6 -89.5 0.81 7.7 0.586   20 6.3
2-butanol C4H10O 99.5 -114.7 0.808 18.1 0.506   100  
i-butanol C4H10O 107.9 -108.2 0.803 8.5 0.552      
2-butanone C4H8O 79.6 -86.3 0.805 25.6 0.327 0.51 200 105
t-butyl alcohol  C4H10O 82.2 25.5 0.786 M 0.389   100 41
carbon disulfide CS2 46.3 -111.6 1.263 0.2 0.065 0.15  10 400
carbon tetrachloride CCl4 76.7 -22.4 1.594 0.08  0.052 0.18 5 120
chlorobenzene C6H5Cl 132 -45.6 1.106 0.05 0.188 0.30 10 12
chloroform  CHCl3 61.2 -63.5 1.498 0.8 0.259   10 210
cyclohexane C6H12 80.7 6.6 0.779 0.005 0.006 0.04 100 104
cyclohexanol C6H12O 161.1 25.2 0.962 4.2 0.509   50 1.2
cyclohexanone C6H10O 155.6 -16.4 0.948 2.3 0.281   25 5
di-n-butylphthalate C16H22O4 340 -35 1.049 0.0011 0.272      
1,1-dichloroethane C2H4Cl2 57.3 -97.0 1.176 0.5 0.269   100 240
diethylene glycol C4H10O3 245 -10 1.118 M 0.713     0.027
diglyme C6H14O3 162 -64 0.945 M 0.244      
dimethoxyethane (glyme) C4H10O2 85 -58 0.868 M 0.231      
N,N-dimethylaniline C8H11N 194.2 2.4 0.956 0.14 0.179      
dimethylformamide (DMF) C3H7NO 153 -61 0.944 M 0.386   10 3.5
dimethylphthalate C10H10O4 283.8 1 1.190 0.43 0.309      
dimethylsulfoxide (DMSO) C2H6OS 189 18.4 1.092 M 0.444 0.75    
dioxane  C4H8O2 101.1 11.8 1.033 M 0.164 0.56 20 41
ethanol  C2H6O 78.5 -114.1 0.789 M 0.654 0.88 100 59
ether C4H10O 34.6 -116.3 0.713 7.5 0.117 0.38 400 587
ethyl acetate C4H8O2 77 -83.6 0.894 8.7 0.228 0.58 400 97
ethyl acetoacetate C6H10O3 180.4 -80 1.028 2.9 0.577      
ethyl benzoate C9H10O2 213 -34.6 1.047 0.07 0.228      
ethylene glycol  C2H6O2 197 -13 1.115 M 0.790 1.11    
glycerin C3H8O3 290 17.8 1.261 M 0.812      
heptane C7H16 98 -90.6 0.684 0.0003 0.012   400 48
1-heptanol C7H16O 176.4 -35 0.819 0.17 0.549      
hexane C6H14 69 -95 0.655 0.0014 0.009 0.01 50 160
1-hexanol C6H14O 158 -46.7 0.814 0.59 0.559      
methanol CH4O 64.6 -98 0.791 M 0.762 0.95 200 128
methyl acetate C3H6O2 56.9 -98.1  0.933 24.4 0.253    200 220
methyl t-butyl ether (MTBE) C5H12O 55.2 -109 0.741 4.8 0.124 0.20    
methylene chloride CH2Cl2 39.8 -96.7 1.326 1.32 0.309 0.42 50 475
1-octanol C8H18O 194.4 -15 0.827 0.096 0.537      
pentane C5H12 36.1 -129.7 0.626 0.004  0.009 0.00 600 573
1-pentanol C5H12O 138.0 -78.2 0.814 2.2 0.568      
2-pentanol C5H12O 119.0 -50 0.810 4.5 0.488      
3-pentanol C5H12O 115.3 -8 0.821 5.1 0.463      
2-pentanone C5H10O 102.3 -76.9 0.809 4.3 0.321      
3-pentanone C5H12O 101.7 -39.8 0.814 3.4 0.265   200  
1-propanol C3H8O 97 -126 0.803 M 0.617 0.82    
2-propanol C3H8O 82.4 -88.5 0.785 M 0.546 0.82 400 44
pyridine C5H5N 115.5 -42 0.982 M 0.302 0.71 5 20
tetrahydrofuran(THF) C4H8O 66 -108.4 0.886 30 0.207 0.57 200 200
toluene C7H8 110.6 -93 0.867 0.05 0.099 0.29 50 29
water H2O 100.00 0.00 0.998 M 1.000 >>1    
water, heavy  D2O 101.3 4 1.107 M 0.991    
p-xylene C8H10 138.3 13.3 0.861 0.02 0.074 0.26 100 15

1    M = miscible.
2    The values for relative polarity are normalized from measurements of solvent shifts of absorption spectra and were
      extracted from Christian Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH Publishers, 3rd ed., 2003.
3     Snyder's empirical eluant strength parameter for alumina.  Extracted from Reichardt, page 495.
4   Threshold limits for exposure.  Extracted from Reichardt, pages 501-502.

TABLE 2

Solvent formula boiling point (oC) melting point (oC)  density 
(g/mL)
solubility in H2O1  (g/100g) relative
polarity2
eluant strength3 threshold limits4 (ppm) vapor pressure 20oC (hPa)
cyclohexane C6H12 80.7 6.6 0.779 0.005 0.006 0.04 100 104
pentane C5H12 36.1 -129.7 0.626 0.0039  0.009 0.00 600 573
hexane C6H14 69 -95 0.655 0.0014 0.009 0.01 50 160
heptane C7H16 98 -90.6 0.684 0.0003 0.012   400 48
carbon tetrachloride CCl4 76.7 -22.4 1.594 0.08  0.052 0.18 5 120
carbon disulfide CS2 46.3 -111.6 1.263 0.2 0.065 0.15  10 400
p-xylene C8H10 138.3 13.3 0.861 0.02 0.074 0.26 100 15
toluene C7H8 110.6 -93 0.867 0.05 0.099 0.24 50 29
benzene C6H6 80.1 5.5 0.879 0.18 0.111 0.32 0.5 101
ether C4H10O 34.6 -116.3 0.713 7.5 0.117 0.38 400 587
methyl t-butyl ether (MTBE) C5H12O 55.2 -109 0.741 4.8 0.124 0.20    
diethylamine C4H11N 56.3 -48 0.706 M 0.145 0.63 5 260
dioxane  C4H8O2 101.1 11.8 1.033 M 0.164 0.56 20 41
N,N-dimethylaniline C8H11N 194.2 2.4 0.956 0.14 0.179      
chlorobenzene C6H5Cl 132 -45.6 1.106 0.05 0.188 0.30 10 12
anisole C7H8O 153.7 -37.5 0.996 0.10 0.198      
tetrahydrofuran  (THF) C4H8O 66 -108.4 0.886 30 0.207 0.57 200 200
ethyl acetate C4H8O2 77 -83.6 0.894 8.7 0.228 0.57 400 97
ethyl benzoate C9H10O2 213 -34.6 1.047 0.07 0.228      
dimethoxyethane (glyme) C4H10O2 85 -58 0.868 M 0.231      
diglyme C6H14O3 162 -64 0.945 M 0.244      
methyl acetate C3H6O2 56.9 -98.1 0.933 24.4 0.253    200 220
chloroform  CHCl3 61.2 -63.5 1.498 0.8 0.259 0.40 10 210
3-pentanone C5H12O 101.7 -39.8 0.814 3.4 0.265   200  
1,1-dichloroethane C2H4Cl2 57.3 -97.0 1.176 0.5 0.269   100 240
di-n-butyl phthalate C16H22O4 340 -35 1.049 0.0011 0.272      
cyclohexanone C6H10O 155.6 -16.4 0.948 2.3 0.281   25 5
pyridine C5H5N 115.5 -42 0.982 M 0.302 0.71 5 20
dimethylphthalate C10H10O4 283.8 1 1.190 0.43 0.309      
methylene chloride CH2Cl2 39.8 -96.7 1.326 1.32 0.309 0.42 50 475
2-pentanone C5H10O 102.3 -76.9 0.809 4.3 0.321      
2-butanone C4H8O 79.6 -86.3 0.805 25.6 0.327 0.51 200 105
1,2-dichloroethane C2H4Cl2 83.5 -35.4 1.235 0.87 0.327      
benzonitrile C7H5N 205 -13 0.996 0.2 0.333   10 12
acetone C3H6O 56.2 -94.3 0.786 M 0.355 0.56 500 240
dimethylformamide (DMF) C3H7NO 153 -61 0.944 M 0.386   10 3.5
t-butyl alcohol  C4H10O 82.2 25.5 0.786 M 0.389   100 41
aniline C6H7N 184.4 -6.0 1.022 3.4 0.420   2 0.4
dimethylsulfoxide (DMSO) C2H6OS 189 18.4 1.092 M 0.444 0.75    
acetonitrile C2H3N 81.6 -46 0.786 M 0.460 0.65 20 97
3-pentanol C5H12O 115.3 -8 0.821 5.1 0.463      
2-pentanol C5H12O 119.0 -50 0.810 4.5 0.488      
2-butanol C4H10O 99.5 -114.7 0.808  18.1 0.506   100  
cyclohexanol C6H12O 161.1 25.2 0.962 4.2 0.509   50 1.2
1-octanol C8H18O 194.4 -15 0.827 0.096 0.537      
2-propanol C3H8O 82.4 -88.5 0.785 M 0.546 0.82 400 44
1-heptanol C7H16O 176.4 -35 0.819 0.17 0.549      
i-butanol C4H10O 107.9 -108.2 0.803 8.5 0.552      
1-hexanol C6H14O 158 -46.7 0.814 0.59 0.559      
1-pentanol C5H12O 138.0 -78.2 0.814 2.2 0.568      
acetyl acetone C5H8O2 140.4 -23 0.975 16 0.571      
ethyl acetoacetate C6H10O3 180.4 -80 1.028 2.9 0.577      
1-butanol C4H10O 117.6 -89.5 0.81 7.7 0.586   20 6.3
benzyl alcohol C7H8O 205.4 -15.3 1.042 3.5 0.608      
1-propanol C3H8O 97 -126 0.803 M 0.617 0.82    
acetic acid C2H4O2 118 16.6 1.049 M 0.648 >1 10 15.3
2-aminoethanol C2H7NO 170.9 10.5 1.018 M 0.651   3 0.53
ethanol  C2H6O 78.5 -114.1 0.789 M 0.654 0.88 1000 59
diethylene glycol C4H10O3 245 -10 1.118 M 0.713     0.027
methanol CH4O 64.6 -98 0.791 M 0.762 0.95 200 128
ethylene glycol  C2H6O2 197 -13 1.115 M 0.790 1.11    
glycerin C3H8O3 290 17.8 1.261 M 0.812      
water, heavy  D2O 101.3 4 1.107 M 0.991      
water H2O 100.00 0.00 0.998 M 1.000 >>1    

Spectra (of solvents and other compounds) 

1. ir, nmr, mass spectra
   
Aldrich - http://www.sigmaaldrich.com/
    NIMC site - http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng 
    RSC - http://www.rsc.org/education/teachers/learnnet/spectra/index2.htm

2. ir, mass spectra, uv-vis
   
NIST site - http://webbook.nist.gov/chemistry/ 

3. ir
   
 Acros - http://www.acros.com/portal/alias__Rainbow/lang__en/tabID__21/DesktopDefault.aspx
     ChemExper Chem Directory -  http://www.chemexper.com/           

4. nmr
       

human metabolites - http://hmdb.ca/  (also some mass spectra)
        bioorganics - http://mmcd.nmrfam.wisc.edu/mmcdbrowse.html

     Solvents - http://www.alsnotebook.com/chlorformtraces.html 
           
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Why is acetonitrile more polar than acetaldehyde