1197

Appendix C

PHYSICOCHEMICAL PROPERTIES OF ORGANIC COMPOUNDS

Appendix C contains the names, molecular formula, molar mass (MJ, density (pi), melting point (Tm), boiling point (Tb), vapor pressure ( P:), aqueous solubility ( Czt ), air-water partition constant (Kjaw), octanol-water partition constant (Kio,,,), and acidity constant (Kia, where appropriate) of some environmentally relevant organic chemicals. Except for density (20°C), all data are given for 25°C. The data have been collected from various data compilations (and references cited therin) including Abraham et al. (1 994a and b), Hansch et al. (1 995), Lide (1 998), Mackay et al. (1992-97), Mitchell and Jurs (1998), Montgomery (1997), and Ruelle and Kesselring (1 997a and b).

Environmental Organic Chemistry, 2nd Edition. Rene P. Schwarzenbach, Philip M. Gschwend and Dieter M. Imboden

Copyright 0 2003 John Wiley &L Sons, Inc.

Compound Name Molecular Formula

r

\o 00

log p,*lPa -log q G t -logH;,, myow PK;, w calculated

(experimental)

Methane Ethane Propane n-Butane n-Pentane n-Hexane n-Heptane n-Octane n-Nonane n-Decane n-Undecane n-Dodecane n- Hexadecane n-Octadecane

2-Methylpropane (isobutane) C A 0

2-Methylbutane (isopentane) C5H12

2,2-Dimethylpropane (neopentane) C5H12

2,2-Dimethylbutane (neohexane) C6H14 2,2,4-Trimethylpentane (isooctane) C8H,8

2-Methylpentane (isohexane) C6H14

1.3-Butadiene 2-Methyl-I ,3-butadiene (isoprene) 1 ,4-Pentadiene Cyclopentene Cyclopentane 1 ,4-Cyclohexadiene Cyclohexene Cyclohexane 1 -Hexene Methylcyclohexane

C4H6

C5H8

C5H8 C5H8

C5H10

C6H10

C6H12

C6H12

C7H14

16.0 30.1 44.1 58.1 72.2 86.2

100.2 11 4.2 128.3 142.3 156.3 170.3 226.4 254.4

n-Alkanes

-1 82.5 -1 83.3 -1 89.7

0.58 (L) -138.4 0.63 -1 29.7 0.66 -95.0 0.68 -90.6 0.70 -56.8 0.72 -51 .O 0.73 -29.7 0.74 -25.6 0.75 -9.6 0.77 18.2 0.78 28.2

-1 64.0 -88.6 -42.1 -0.5 36.1 69.0 98.4

125.7 150.8 174.1 195.9 21 6.3 287.0 31 6.1

Branched A/kanes

58.1 0.56 (L) -159.4 -11.7 72.2 0.62 -159.9 27.9 72.2 0.59 (L) -16.6 9.5 86.2 0.64 -153.8 60.1 86.2 0.65 -99.8 49.7

11 4.2 0.69 -107.4 99.2

54.1 68.1 68.1 68.1 70.1 80.1 82.1 84.2 84.2 98.2

Unsaturated and Ahicychic ffydrocarbons

0.62 (L) 0.68 0.66 0.77 0.74 0.85 0.81 0.78 0.67 0.77

-1 08.9 -1 46.0 -1 48.3 -1 35.1 -92.9 -49.2

-1 03.5 6.5

-1 39.8 -1 26.6

-4.4 34.0 26.0 44.2 49.2 81.5 83.0 80.7 63.4

100.6

7.45 6.61 5.98 5.40 4.83 4.30 3.79 3.26 2.76 2.24 1.72 1.19

-0.73 -1.78

5.56 4.96 5.24 4.45 4.63 3.81

5.45 4.86 5.00 4.70 4.63 3.95 4.07 4.10 4.40 3.79

2.82 (1 bar) 2.69 (1 bar) 2.85 (1 bar) 2.98 (1 bar) 3.25 3.83 4.53 5.20 5.77 6.42

-1.43 -1.30 -1.46 -1.58 -1.69 -1 -74 -1.93 -2.07 -2.14 -2.27

7.52 -2.32 7.80 -0.68 8.08 -0.09

1.09 1.81 2.36 2.89 3.39 4.00 4.66 5.15 5.65 6.25

3.07 (1 bar) -1.68 2.82 3.18 -1.75 3.34 (1 bar) -1.95 3.11 3.80 -1.86 3.60 3.65 -1.89 3.42 4.67 -2.09

1.86 2.04 2.08 2.09 2.64 2.03 2.60 3.17 3.22 3.81

-0.47 -0.51 -0.69 -0.40 -0.88

0.41 -0.28 -0.89 -1.22 -1.21

1.99 2.05

3.00 2.30 2.86 3.44 3.40 3.88

A/ky/a fed Benzenes

0.88 5.5

0.87 -95.0

0.86 -95.0

0.91 -31 .O

0.88 -25.2

0.86 -47.8

0.86 13.3

0.86 -99.6 0.86 -96.6 0.89 -25.4 0.88 -43.8 0.88 -44.7 0.88 -83.8 0.86 -62.4 0.86 -88.0 0.86 -75.0 0.87 -58.0 0.91 -6.3 0.84 79.5 0.86 -78.3 0.86 -61 .O

166.7

Benzene

Methylbenzene (toluene)

Ethylbenzene

Vinylbenzene (styrene)

1 ,PDimethylbenzene (0-xylene)

1,3-Dimethylbenzene (m-xylene)

1,4-Dimethylbenzene (p-xylene)

n-Propylbenzene lsopropylbenzene 1,2,3-TrimethyIbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 1 -Ethyl-2-methylbenzene 1 -Ethyl-4-methylbenzene n-Butylbenzene s-Butylbenzene f-Butylbenzene 1,2,3,4-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene n-Pentylbenzene n-Hexylbenzene Hexamethylbenzene

lndane Naphthalene

1 -Methylnaphthalene 2-Methylnaphthalene Acenaphthene

Acenaphthylene Fluorene

C6H6

C,H8

C8HlO

C8HlO

C8HlO

C8HlO

‘gHl2

‘gH12

‘SH12

‘gHl2

‘gH12

‘gH12

‘gHl2

‘10H14

ClOH14

C10H14

C10H14

C10H14

C11H16

C12H18

C12H18

C9H10

C l OH8

Cl lHlO

Cl lHlO

C l 2H10

C12H8

C13HlO

78.1

92.2

106.2

104.2

106.2

106.2

106.2

120.2 120.2 120.2 120.2 120.2 120.2 120.2 134.2 134.2 134.2 134.2 134.2 148.3 162.3 162.3

80.1

11 0.6

136.2

145.1

144.4

139.1

138.1

159.2 154.2 176.1 169.4 164.7 165.2 162.0 183.0 174.0 169.0 205.0 195.9 202.2 226.0 265.0

4.10

3.57

3.09

2.94

2.95

3.04

3.07

2.65 2.79 2.30 2.42 2.52 2.52 2.60 2.15 2.40 2.46 1.65 1 .I1 1.65 1.13

-0.80

Po&cyc/ic Aromatic Hydrocarbons and Re/afed Compounds

118.2 0.96 -51.4 178.0 2.30 128.2 1.16 80.2 218.0 1.05

142.2 1.02 -22.0 244.0 0.92 142.2 1.01 35.0 241.0 0.95 154.2 1.05 96.2 278.0 -0.51

152.2 0.90 92.5 270.0 -0.05 166.2 1.20 116.0 295.0 -1.02

1.65

2.22

2.80

2.53

2.75

2.82

2.77

3.34 3.33 3.23 3.33 3.38 3.20 3.10 3.95 3.73 3.60

4.58 4.59 5.20 5.84

3.03 3.60

3.71 3.75 4.61

4.59 4.94

0.65

0.60

0.50

0.93

0.69

0.53

0.55

0.40 0.27 0.86 0.65 0.50 0.67 0.69 0.29 0.26 0.33

0.70 0.15 0.06 1.35

(0.65 exp.)

(0.62 exp.)

(0.47 exp.)

(0.92 exp.)

(0.68 exp.)

(0.52 exp.)

(0.54 exp.)

1.06 1.74

1.76 1.69 2.29

1.85 2.47

(1.72 exp.)

(2.28 exp.)

(2.39 exp.)

2.17

2.69

3.20

2.95

3.16

3.30

3.27

3.69 3.66 3.60 3.65 3.42 3.53 3.63 4.38 4.44 4.11 4.00 4.10 4.90 5.52 4.75

3.33 3.33

3.87 3.99 4.20

4.00 4.32 w

w W W

Compound Name r

0 0

Molecular fY P, Trn r, -1ogy,, logK;ow PK;, N Formula (g.mol-I) (gem") ("C) ("C)

log p,*lPa -log qCt calculated

(experimental)

Phenanthrene

Anth racene

Fluoranthene

Pyrene

Benzo(a)anthracene Chrysene Benzo(a)pyrene

Perylene

C hloromethane Dichloromethane

Trichloromethane

Tetrachloromethane

1 ,I -Dichloroethane

1,2-Dichloroethane

1 , I ,1-Trichloroethane

l11,2-Trichloroethane

1,1,2,2-Tetrachloroethane

Pentachloroethane Hexachloroethane C hloroethene

1 , I -Dichloroethene

c14H10

C14H10

C16H10

C16H10

C18HlZ C,8H,Z CZOHIZ

C,OH,Z

CH3CI CH,CI,

CHCI,

CCI,

CZH4C'Z

CZH4C1Z

CZH3C13

CZH3C13

CZHZC14

C,HCI,

CzH3CI cZc16

CZHZCIZ

CZHZCIZ

CZHZC',

178.2

178.2

202.3

202.3

228.3 228.3 252.3

252.3

50.5 84.9

119.4

153.8

99.0

99.0

133.4

133.4

167.9

202.3 236.7

62.5

96.9

96.9

96.9

0.98 101.0 339.0

1.25 217.5 341.0

1.25 110.5 384.0

1.27 156.0 403.0

1.25 160.6 437.5 1.28 255.0 448.0

176.5 496.0

277.0 503.0

CMoriated C,- to C4-Compouna's

0.92 (L) 1.33

1.48

1.59

1.18

1.25

1.34

1.44

1.60

1.68 2.09 0.91 (L)

1.22

1.27

1.27

-97.7 -95.1

-63.3

-23.0

-97.3

-35.5

-31.4

-37.0

-40.8

-29.0 187.5

-1 53.8

-1 22.0

-81 .O

-50.0

-24.2 40.1

61.4

76.7

57.3

83.6

73.9

11 3.6

146.3

160.8 187.5 -1 3.7

31.7

60.0

48.0

-1.66

-3.01

-2.91

-3.09

-4.60 -6.22 -6.15

-7.85

5.76 4.76

4.40

4.16

4.49

4.05

4.22

3.60

2.90

2.79 1.70 5.55

4.90

4.45

4.61

5.20

6.60

5.96

6.16

7.32 8.05 8.14

8.80

2.85

2.80

3.34

3.32

3.68 4.56 4.79

5.44

(2.93 exp.)

(2.77 exp.)

(3.35 exp.)

(3.36 exp.)

(4.86 exp.)

4.57

4.68

5.23

5.13

5.91 5.81 6.13

6.25

0.98 (lbar) 0.42 0.70 0.93

1.15 0.84 (0.97 exp.)

(0.82 exp.)

(0.05 exp.)

(0.62 exp.)

(1.30 exp.)

(0.1 5 exp.)

(1.40 exp.)

(1.85 exp.)

2.27 -0.04

1.29 0.61

1.07 1.27

2.01 -0.16

1.47 1.32

1.71 1.78

2.61 0.99 3.68 1.01 1.35 (1 bar) -0.04

1.59 -0.10

1.28 0.66

1.19 0.59

(-0.05 exp.)

(-0.03 exp.)

(0.79 exp.)

(0.46 exp.)

0.91 1.31

1.95

2.77

1.79

1.46

2.49

2.34

2.39

3.22 3.93 1.27

1.48

1.86

2.09

Trichloroethene C,HCI,

Tetrachloroethene c2c14

3-Chloro-1 -propene C3H5CI

Bromomethane Dibromomethane

CH,Br CH,Br,

Tribromomethane CHBr,

Bromoethane C,H5Br

Bromoethene C,H,Br lodomethane CH31

1 ,e-Dibromoethane C!2H4Br2

lodoethane C2H51

Bromochloromethane CH,BrCI Bromodichloromethane C H BrCI, Dichlorodifluoromethane CCI,F, (Freon 12) Trichlorofluoromethane CCI,F (Freon 11) 1,l ,2-Trichloro-l,2,2-trifluoroethane C,CI,F, (Freon 11 3) 1,1,2,2-Tetrachloro-l ,Pdifluoroethane C,C14F, (Freon 11 2)

Chlorobenzene C6H,CI

131.4 1.46 -73.0 87.0 4.00

165.8 1.62 -22.4 121.1 3.40

76.5 0.94 -135.0 44.9 4.70

Brominated and Iodated C - and C,-Compound

94.9 1.68 (L) -93.6 3.6 5.34 173.9 2.50 -52.6 96.7 3.81

252.8 2.89 8.3 149.6 2.86

109.0 1.45 -119.0 38.4 4.80 187.9 2.18 9.8 131.5 3.21 107.0 1.49 (L) -139.5 15.8 5.15 141.9 2.28 -66.5 42.5 4.73

156.0 1.94 -111.0 72.4 4.26

Mixed Ha/ogenated C - and C2-Compounds

129.4 163.8 120.9

137.4

187.4

203.8

11 2.6

147.0

147.0

147.0

181.5 181.5 181.5

1.93 -88.0 1.97 -57.1 1.33 (L) -158.0

1.18 -111.0

1.57 -35.0

1.64 -25.5

Ch/orobenzenes

1.11 -45.2

1.30 -1 7.0

1.29 -24.7

1.25 53.1

1.69 52.0 1.45 17.0 1.39 63.5

68.1 90.0

-29.8

23.8

47.6

92.8

132.0

180.0

173.0

174.0

21 8.5 21 3.5 208.0

4.29 3.82 5.75

5.03

4.68

3.87

3.20

2.30

2.45

2.05

1.45 1.58 1.50

2.08 0.31 (0.40 exp.)

(0.1 2 exp.)

(0.42 exp.)

3.07 -0.08

1.33 0.36

0.79 (1 bar) 0.35 1.18 1.40

1.91 1.62

1.09 1.50 1.63 1.55

(1.20 exp.)

(1.72 exp.)

1.01 0.66

1.60 0.53 (0.65 exp.)

0.94 1.16 1.55 1.01 2.64 (1 bar) -1.25

2.10 (lbar) -0.71 (-1.18 exp.)

(-0.61 exp.)

(-1.11 exp.) 3.04 -1.29

3.23 -0.71

2.39 0.80

3.05 1.04

3.08 0.86

3.30 1.04

3.94 1.01 3.78 1.03 4.53 0.36

(0.82 exp.)

(1 .OO exp.)

(0.82 exp.)

(1.10 exp.)

2.42

2.88

1.45

1.19 1.88

2.67

1.61 1.96 1.57 1.51

2.00

1.41 2.10 2.16

2.53

3.16

3.73

2.78

3.40

3.47

3.45

4.14 4.06 4.19

Compound Name Molecular Formula

c-r -log q.y' -logYaw logK0, PK, t 4

calculated t 4 0

(experimental)

1,2,3,4-Tetrachlorobenzene C6H2C14

1,2,3,5-TetrachIorobenzene C6H2C14

1,2,4,5-TetrachIorobenzene C6H2C'4

Pentachlorobenzene C6HC15

Hexachlorobenzene c6c16

Biphenyl 2-CBP (PCB1) 4-CBP (PCB3) 2,2'-CBP (PCB4) 2,4-CBP (PCB7) 2,4'-CBP (PCB8) 4,4'-CBP (PCB15) 2,2',5-CBP (PCBI 8) 2,4,4'-CBP (PCB28) 2,4,5-CBP (PCB29) 2,2',4,4'-CBP (PCB47) 2,2',5,5'-CBP (PCB52)

3,3',4,4'-CBP (PCB77) 2,2',3,4,5'-CBP (PCB87) 2,2',4,5,5'-CBP (PCB101) 2,2',4,4',5,5'-CBP (PCBl53) 2,2,3,4,4,5,5'-CBP (PCBl80)

C12HlO

ClZH9CI Cl2H8CIZ C l 2H8CIZ C1zHaC'z C12H8CIZ

'1 2 H9CI

C1ZH7C'3

C12H7Ci3

'1 ZH7C13

'1 2H6C14

'1 2 H6C14

'1 ZH6'I4 C1ZH5C15

C12H5C15

C12H4C16

'1 2H&17

a hexachlorocyclohexane (a-HCH) C6H6C16 p hexachlorocyclohexane (6-HCH) C,H,CI,

(lindane, yHCH) y hexachlorocyclohexane C6H6C16

p,p'DDT 1 4H9C '5

AP' -D DE C14H8Ci4

A P' -D DD C14H10C'4

21 5.9 47.5 254.0 0.75 21 5.9 1.86 54.5 246.0 1 .oo 21 5.9 140.0 243.0 -0.14

250.3 1.83 86.0 277.0 -0.66 284.8 2.08 230.0 322.0 -2.60

Po/ychlohafed Biphenys (PCBs), Selecfed Congeners

154.2 0.87 71.0 255.9 0.11 188.6 0.98 34.0 274.0 -0.30 188.6 0.98 77.7 291.0 -0.57 223.1 1.05 61 .O -0.58 223.1 1.05 24.4 -0.60 223.1 1.05 45.0 -1 . I0 223.1 1.05 148.5 -2.30 257.5 1.15 44.0 -0.84 257.5 i . i5 57.5 -1.70 257.5 1.15 78.5 -1.95 292.0 1.20 41.5 -2.00 292.0 1.20 86.5 -2.30 292.0 1.20 180.0 326.4 1.28 11 2.0 -3.52 326.4 1.28 77.0 -2.96 360.9 103.5 -3.92 395.4 109.5

Miscelanous Po/ych/oflhafed Compounds

290.8 158.0 -2.52 290.8 309.5 -4.40 290.8 11 2.0 -2.15

354.5 1.55 109.0 31 8.0 89.0 320.0 109.5

-4.70 -3.20 -3.90

4.69 4.79 5.23 5.58 7.55

4.34 4.54 5.19 5.35 5.25 5.35 6.57 5.80 6.20 6.26 6.51 6.99 7.47 7.91 7.51 8.55

5.28

6.46 4.60

7.80 6.90 6.80

k 0.95 4.64 0.60 4.66 'd x 1.30 4.72 5

E 1.47 5.18 1.44 5.80

x

(1.54 exp.)

1.93 4.01 1.55 4.53 1.77 4.61 1.62 4.97 1.74 5.30 2.14 5.10 2.12 5.33 1.43 5.60 1.89 5.62 2.08 5.90 1.88 6.29

1.70 6.09 6.50

2.00 6.37 1.83 6.36 1.76 7.15 2.36 7.36

3.63 3.81

4.33 3.80 3.94 3.78

3.30 6.36 2.69 5.70 3.49 5.50

Dimethyl ether Diethyl ether Methyl- t-butyl-ether (MBTE) Di-n-propyl ether Di-isopropyl ether n-Butyl-ethyl ether D-n-butyl ether

Ethylene oxide (epoxyethane) Propyleneoxide (epoxypropane) Tetrahydrofuran 1,4-Dioxane 1 -Chloro-2,3-epoxypropane (epichlorohydrine) Di-2-chloroethyl ether Methoxybenzene (anisole) Ethoxybenzene (phenetole) Styreneoxide

Dibenzo-p-dioxin (DD) 1-CDD 2,7-DCDD 1,2,3,4-TCDD 2,3,7,8-TCDD 1,2,3,4,7-PCDD 1,2,3,4,7,8-HCDD Octachloro-DD

Dibenzofuran (DF) 2,8-DCDF 2,3,7,8-TCDF 2,3,4,7,8-PCDF 1,2,3,4,7,8-HCDF Octachloro-DF

AhNhatic Ethers

46.1 0.67 -141.5 -24.8 74.1 0.71 -116.3 34.5 88.2 0.74 -109.0 55.2

102.2 0.75 -123.2 90.1 102.2 0.73 -85.5 68.5 102.2 0.75 -103.0 92.2

130.2 0.77 -95.2 140.3

Misce//aneous Ethers /nc/udng Epoxides

44.1 0.87 -111.0 10.7 58.1 0.83 -112.1 34.2 72.1 0.89 -108.5 66.0 88.1 1.03 11.0 101.1 92.5 1.18 -57.2 116.2

143.0 1.22 -46.8 178.0 108.2 0.99 -37.5 153.6 122.2 1.07 -31.0 169.5 120.2 1.05 -35.6 194.1

5.77

4.85 4.51 3.92 4.30 3.90 2.95

5.16 4.85 4.33 3.70 3.36

2.31 2.67 2.31 1.60

Po/ych/oflnated Dibenzo-p-Dioxins (FCDDs), Se/ected Congeners

C12H802 184.0 123.0 283.5 -1.26

C12H,CI0, 218.5 105.5 315.5 -1.92

C12H6C1202 253.0 210.0 373.5 -3.92

Cl,H,C140, 322.0 190.0 419.0 -5.20

C12H4CI,02 322.0 305.0 446.5 -6.70

C12H,CI,02 356.4 196.0 464.7 -7.05

C12H2C1602 391 .O 273.0 487.7 -8.29 460.0 322.0 510.0 -1 0.00 Cl 2CP2

Po/ych//Onated Dibenzo furans (PCDFs), Se/ected Congeners

C12H80 168.2 86.5 287.0 -0.52

C,,H6C120 237.1 184.0 375.0 -3.41

C12H,C140 306.0 227.0 438.0 -5.70

Cl2H3CI50 340.4 1196.0 464.7 -6.46

C12H2C160 374.9 225.5 487.7 -7.50

c12c1602 443.8 258.0 537.0 -9.30

(1.40 exp.) 0.05 1.49 0.34 1.54 1.50 0.97

1.10 0.98 1.20 I .29

2.75 0.69

-0.93 (1 bar) -0.91 miscible (2.55 exp.) miscible (3.71 exp.)

0.15 2.88

1.15 2.93 1.80 1.92 2.18 1.90 1.63 3.16

5.33 5.72 7.83 8.77

10.22 9.48

10.94 12.79

2.32 2.59 2.48 2.82 2.87 3.96 3.74 3.60

4.55 2.36 7.21 2.59 8.86 3.23 9.16 3.87

10.66 3.23 11.58 4.11

0.10

0.89 0.94 2.03 1.52 2.03

3.21

-0.30 0.03 0.46

0.30

1.29 2.11 2.51 1.55

-0.27

4.30 4.90 5.70 6.60 6.80 7.40 7.80 8.20

4.31

5.44 6.10 6.50 7.00 8.00

c)

Y

w Compound Name Molecular Y P, Gl r, log p,*lPa -log q;' -l0gYaw logK;,, PK;, t4 0 A calculated

(experimental) Formula (g.mol-') (gcma) ("C) ("C)

Phenol

2-Methylphenol (0-cresol)

3-Methylphenol (m-cresol) 4-Methylphenol (p-cresol)

4-Ethylphenol 2,6-Dimethylphenol

3,CDimethylp henol 2,4,6-Trimethylp henol 4-n-Butylp henol 4- t-Butylphenol 4-n-Octylp henol 4-n-Nonylphem!

2-Chlorophenol 3-C hlorophenol 4-C hlorophenol 2,4-Dichlorophenol 2,4,5-Trichlorophenol 2,4,6-Trichlorophenol 2,3,4,5-Tetrachlorophenol 2,3,4,6-Tetrachlorophenol Pentachlorophenol

2-Nitrophenol

3-Nitrophenol 4-Nitrophenoi 2,4-Dinitrophenol 2,4-Dinitr0-6-methylphenol (dinitro-ocresol; DNOC)

C6H60

C7H80

C7H80

C7H80

C8H100

C,Hl,O

C9H12O C8H100

'1 OH,,'

C10H140

C14H220

C15H24G

C,H,CIO C,H,CIO C,H,CIO C6H4CI,0 C,H,CI,O C,H,CI,O C,H2CI,0

C,H,CI,O C6HCI,0

C6H!iN03

C6H5N03

c6H5N03

C6H4N2'5

C7H6N205

94.1

108.1

108.1 108.1

122.2 122.2

122.2 136.2 150.2 150.2 206.3 220.4

128.6 128.6 128.6 163.0 197.5 197.5 231.9 231.9

266.3

139.1

139.1 139.1 184.6 198.1

A/ky/ated Pheno/s

1.05 40.9 181.8

1.05 30.7 191.0

1.03 11.9 202.1 1.03 35.2 201.9

1.03 47.0 219.0 1.13 49.0 203.0

1.14 67.0 72.0

0.98 22.0 248.0 99.0 238.0 41.5

1.51 96.0 295.0

Ch/orinted Pbeno/s

1.26 9.8 175.2 1.25 32.6 214.0 1.31 42.7 219.0 1.38 43.7 213.0 1.50 62.5

68.8 243.5 11 7.0 69.5

189.3

Nifropbeno/s

1.55 44.7 215.0

96.5 1.48 11 4.0

114.1 86.5

1.79 0.005

1.60 0.61

1.30 0.67 1.20 0.75

0.80 1.18 1.28 1.29

-0.07 1.40 0.82 2.10

2.31 0.08 2.11

-1.14 4.18 -1.15 4.64

2.50 0.65 1.54 0.69 1.27 0.68 1.20 1.57 0.62 2.22 0.37 2.37

-1 .oo 3.15 -0.55 3.10 -2.04 4.15

1.26 2.03

1.03 -2.26 0.98

2.74 -1 . I4 3.00

4.59

4.18

4.42 4.44

4.40 3.70

5.06 3.47

4.20 3.35 2.89

(4.79 exp.)

(4.30 exp.)

(4.49 exp.)

(3.56 exp.)

3.24 4.16 4.43

3.61 3.55 3.65 4.24 3.84 4.28

3.10 (3.40 exp.)

7.66

4.53

1.98 10.05 1.93 10.25

2.50 10.00 2.36 10.63

2.23 10.34 2.73 10.90 3.64 3.14 9.90

5.76

2.19 8.44 2.48 8.98 2.42 9.29 3.09 7.85 3.90 6.91 3.67 6.19 4.87 6.35 4.45 5.40 5.24 4.83

1.78 7.15

2.00 8.36 1.96 7.06 1.66 4.01 2.12 4.31

Misce//aneous PhenoLc Compounds

1,2-Dihydroxybenzene (catechol)

1,3-Dihydroxybenzene (resorcinol)

1,4-Dihydroxybenzene (hydroquinone) 2-Methoxyphenol (guaiacol)

4,5-Dichloro-2-rnethoxyphenol (4,5-dichloroguaiacoI) 3,4,5-trichloro-2-methoxyphenol (3,4,5-Trichloro-guaiacol) 4,5,6-Trichloro-2-methoxyphenol (4,5,6-trichloro-guaiacol) Tetrachloro-2-methoxyphenol (tetrachloroguaicol)

Methanal (formaldehyde) Ethanal (acetaldehyde) Propanal nButanal (butyraldehyde)

iso-Butanal (isobutyraldehyde) n-Pentanal (valeraldehyde) Hexanal

2-Propenal (acrolein) Benzaldehyde

Propanone (acetone) Butanone 2-Pentanone

2-Hexanone Cyclohexanone Methyl-phenyl-ketone (acetop hen one) Diphenylketone (benzophenone)

110.1

110.1

110.1

124.1

193.0

227.5

227.5

261.9

30.0 44.1 58.1 72.1

72.1 86.1

100.2

56.1 106.1

58.1 72.1 86.1

100.2 98.1

120.2

182.2

1.15

1.27

1.33

0.78 0.87 0.80

0.81 0.85

0.84 1.04

0.79 0.81 0.81

0.81 0.95 1.03

104.0

110.0

172.0

32.0

74.0

85.5

113.5

121.5

Aldehydes

-92.0 -1 23.0 -80.0 -96.4

-65.0 -93.5 -56.0

-87.3 -26.0

Ketones

-94.7 -87.0 -76.9

-55.8 -32.1

19.6

48.0

245.0

277.0

287.0

205.0

-21 .oo 20.8 48.0 74.8

64.1 103.0 131.0

52.6 178.8

56.1 79.6

102.3

128.6 155.6 202.0

305.4

-0.65

-2.93

-2.59

1.32

-0.24

-0.79

-1.49

-1.80

5.72 5.08 4.63 4.19

4.36 3.66 3.17

4.56 2.24

4.50 4.09 3.70

3.20 2.78 1.67

-1.05

0.39

0.00

0.20

0.70

2.52

2.86

3.62

4.00

0.01

1.30

1.55

miscible

0.16

0.76 0.63 1.35

2.82

(6.65)

(9.32)

(8.78)

4.38

4.11

4.32

4.26

4.19

(4.28 exp.)

(4.90 exp.) (2.52 exp.) (2.50 exp.)

(2.33 exp.) (2.10 exp.) (2.22 exp.)

(2.06 exp.) (2.27 exp.)

(2.95 exp.)

2.20

1.92

2.60

(2.80 exp.) (2.60 exp.)

2.53 (2.58 exp.)

2.43 2.98 3.37

4.62

0.88

0.80

0.59

1.32

3.26

3.77

3.74

4.45

0.45 0.59 0.88

1.78

-0.01 1.48

-0.24 0.29 0.90

1.38 0.71 1.63

3.18

9.34 12.60 9.32

11.10 9.85

11.40

8.52

7.56

7.07

6.26

P

% E

’d

3

x

CI -lOgy,, ~0gYow Py, t4

calculated Q\

log p,?lPa -log C:' 0

Compound Name Molecular 4. Pi am Tb Formula (g.mol-I) (gcm4) ("C) ("C)

(experimental)

Acetic acid Propanoic acid Butanoic acid (butyric acid)

Hexanoic acid Benzoic acid Phenylacetic acid Salicylic acid (2-hydroxy benzoic acid) o-Phthalic acid

Methyl acetate

Ethyl acetate

Propyl acetate

Butyl acetate

Hexyl acetate Vinyl acetate Methyl benzoate Ethyl benzoate

Dimethylphthalate Diethylphthalate Di-n-propyl-phthalate Di-n-butyl-phthalate Benzys-n-butyl-phthasa~e Di-(2-ethylhexyl)-phthalate

Aminobenzene (aniline) 2-Methylaniline (o-toluidine)

C2H402

C3H602

C4H802

C6H1202

C7H602

C8H802

C7H603

C8H604

C3H602

C4H802

C A 0 0 2

C6H1202

C8H1602

C4H602

C8H802

C9Hl002

'1 O H l 0'4

C12Hl 4'4

8'4

'1 6H2204

1 !3H2004

C24H38Q4

C 6 H P

C 7 H P

60.1 74.1 88.1

116.1 122.1 136.2 138.1

166.1

74.1

88.1

102.1

116.2

144.2 86.1

136.2 150.2

194.2 222.2

250.3 278.3 312.4 390.6

93.1 107.2

Carboxykc Acids

16.7 117.9 0.99 -20.7 141.1 0.96 -5.7 163.7

0.93 -3.5 205.0 1.27 122.4 249.2

77.0 265.0 1.44 159.0 211.0

210.0

Carboxykc Acid Esters

0.93 -98.1 56.9

0.90 -4: .5 77.1

0.89 -95.0 101.5

0.88 -73.5 126.1

0.88 -80.9 171.5 0.93 -92.8 72.5 1.09 -12.1 199.5 1.05 -34.0 212.4

Fhihahtes

1.19 5.5 283.7 1.23 -40.5 296.0

304.5 1.05 -35.0 340.0 1 .12 <-35.0 370.0 0.98 -50.0 385.0

Aromatic Amihes

1.01 -6.3 184.4 1 .oo -16.3 200.3

3.32 2.70

2.18

0.70 -0.96 -0.08 -1.70

4.46

4.10

3.65

3.20

2.27 4.15 1.72 1.38

0.38 -0.66

-2.28 -2.94 -2.72

1.92 1.55

miscible miscible

0.19

1.55 0.92 1.78

1.38

-0.52

-0.04

0.67

1.28

2.46 0.64 1.81 2.63

1.66 2.44 3.36 4.36 5.08 7.13

0.44 0.82

(4.95 exp.) (4.74 exp.)

4.02 (4.66 exp.) (4.56 exp.)

5.80 5.55 5.31

2.45

2.33

2.07

1.91

1.66 1.60 2.86 2.38

(2.04 exp.)

(2.16 exp.)

(2.05 exp.)

(1.94 exp.)

4.35 4.61

4.31 4.25 1.98

4.03 4.02

-0.25 0.33

0.79

1.92 1.89 1.41 2.24

0.73

0.20

0.69

1.24

1.80

2.83 0.73 2.20 2.64

1.53 2.39 3.27 4.61 4.91 7.48

0.95 1.32

> 'd

5 4.75

4.85 3

4.87 4.19 4.31 2.97

13.40 2.89 5.51

4.87 E

4.63 4.44

3-Methylaniline (m-toluidine) 4-Methylaniline (p-toluidine) 2,6-Dimethylaniline 3,4-Dimethylaniline N,N-Dimethylaniline 2-Chloroaniline 3-Chloroaniline 4-C hloroaniline 3,4-Dichloroaniline N-Phenylaniline (diphenylamine) 4,4'-Diaminobiphenyl (benzidine)

C7H9N C,H9N

C*HllN

C8H11N

'BH1l

C,H,CIN C,H,CIN C,H,CIN C,H5C12N

C12HllN C12H12N2

107.2 107.2 121.2 121.2 121.2 127.6 127.6 127.6 162.0 169.2 184.2

0.99 -31.5 1.04 43.7 0.98 11.2

51 .O 2.5

1.21 -1 4.0 1.22 -1 0.3 1.43 71 .O

71 .O 1.16 53.0

120.0

203.3 200.4

214.0 228.0 194.0 208.8 229.5 231.3 272.0 302.0 401 .O

1.42 1.60 1.30

1.95 1.54 0.98 0.40 0.36

-1.22

0.85 1.15 1.41 1.65 2.04 1.53 1.37 1.64 3.24 3.53 2.66

4.12 3.64 3.68

1.40 1.39 1.84 1.84 2.31 1.88 1.99 1.83 2.70 3.50 1.34

4.72 5.17 3.95 5.28 5.12 2.65 3.52 4.00 2.97 0.90 3.57 4.66 3.92 4.15

2.40 3.32 4.04 4.35 2.79 4.08

1 -Naphthylamine 2-Naphthylamine

143.2 143.2

1.13 49.5 300.9 1.06 111.5 306.0

1.92 5.34 5.48

2.25 2.30

Ahphafic Amines

-92.5 -96.0

-1 17.2 -81 .O

0.71 -49.5 0.72 -83.0 0.74 -50.0 0.77 -22.9

Methylamine Dimethylamine Trimethylamine Ethylamine Diethylamine n-Propylamine n-Buthylamine n-Hexylamine

31.1 45.1 59.1 45.1 73.1 59.1 73.1

101.2

-6.5 7.4 2.9

16.6 56.1 48.7 77.9

132.8

5.55 5.31 5.34 5.15 4.50 4.62 4.11 3.07

(3.34 exp.) (3.15 exp.) (2.56 exp.) (3.30 exp.) (2.98 exp.) (3.22 exp.) (3.11 exp.)

(2.90 exp.) 3.07

-0.57 -0.38

0.27 -0.13

0.50 0.32 0.98 2.06

10.80 9.80

10.80 10.90 10.70 10.70

0.25

Heterocycic N-Compound!

0.98 -41.6 115.3 0.94 -66.7 129.4 0.95 -18.1 144.1 0.95 3.7 145.4 0.94 -15.5 163.5 0.92 -6.1 144.1 1.10 -14.8 237.1

Pyridine 2-Methylpyridine (2-picoline) 3-Methylpyridine (3-picoline) 4-Methylpyridine (4-picoline) 2,3-Dimethylpyridine (2,3-lutidine) 2,6-Dimethylpyridine (2,6-lutidine) Quinoline

79.1 93.1 93.1 93.1

107.2 107.2 129.2

3.44 3.18 3.12 2.88 2.62 2.87 0.08

(3.44 exp.) (3.40 exp.) (3.50 exp.) (3.62 exp.) (3.54 exp.) (3.37 exp.)

(4.20 exp.) 4.98

0.65 1 .ll 1.22 1.22 1.65 1.68 2.06

5.25 5.97 5.67 5.99 6.57 +p

6.65 4.90 ?

5 5.40 0

X

1.33

isoquinoline 129.2 1.10 26.5 243.2

Nitrohenzenes

1.20 5.7 210.8 1.16 -9.9 222.0

Nitrobenzene 2-Methylnitrobenzene (2-nitrotoluene)

123.1 137.1

1.48 1.43

1.79 2.35

3.12 2.61

1.85 2.30 U

Compound Name + 0 00

Molecular m pi Jm Tb -10gyaw logy,, PK;, h,

Formula (g.mol-') (gcm") ("C) ("C) log p,*lPa -log qrt

calculated (experimental)

3-Methylnitrobenzene (3-nitrotoluene) 4-Methylnitrobenzene (4-nitrotoluene) 2-C hloronitrobenzene

3-Chloronitrobenzene 4-Chloronitrobenzene

1,3-Dinitrobenzene 1 -Methyl-2,4-dinitrobenzene (2.4-dinitrotoluene) 1,3-Dinitr0-2-methylbenzene (2,6-dinitrotoluene) 1,3,5Trinitrobenzene 2-Methyl-l,3,5-trinitrobenzene (2,4,64rinitrotoluene 'TNT")

Simazine Atrazine Cyanazine Propachlor Alachlor Metolachlor Carbaryl Carbofuran Fenuron Diuron lsoproturon

Tributylphosphate Tri-o-cresylphosphat Parathion Methylparathion Fenthion Disulfoton

C7H7N02

C7H7N02

C6H4CIN02

C6H4CIN02 C6H4CIN02

C6H4N204

C7H6N204

C7H6N204

C6H3N306

C7H5N306

C7H12CIN5

C8H10CIN5

C9H13CIN6

C,,H,,CINO C,,H,,CINO

'1 5H22CIN02 Cl 2% NO2

C9Hl 2N2O

C9HlOCIZNZO Cl 2H18NZO

C12H15N03

'1 2H270,P

137.1 15.9 232.0 1.28

137.1 1.39 51.6 238.3 1.20

157.6 33.0 245.3 0.70

157.6 157.6

45.0 235.6 0.27

83.3 240.5 0.44

168.1 89.9 301.9 -1.92 182.1 1.52 70.3 -1.54

182.1 1.28 65.5 -1.12

213.1 227.1

122.9 80.8

-1.82 -3.07

Piazine-, Carbamide-, Carbama fe-, and Urea Pes fiches

201.7 1.30 226.0 -5.07 21 5.7 1.19 175.0 -4.40 240.7 167.0 -6.67 211.7 1.13 71 .O -1.70 269.8 1.13 41 .O -2.70 283.8 C 25 -2.40 201.2 1.23 142.0 -4.57 221.3 1.18 152.5 -4.12 164.2 1.08 135.5 233.1 1.48 158.5 C-4.0 206.3 1.16 155.5 <-4.0

Pbosphok- and Jbiopbosphoric Acid (Tbio)€sfers

263.3 0.98 CO -0.1 0 368.4 1.21 50 -3.00

2.43

2.43

2.69

2.73 2.92

2.54

2.86

3.00

2.81 3.24

4.55 3.86 3.15 2.55 3.05 2.75 3.22 2.81 1.63 3.76 3.57

2.65 5.31

+ 2.68 2.43

2.76 2.38

!% 3.00 2.45 X

3.39 2.48

3.03 2.50

5.77 1.49 5.25 2.00

4.51 2.03

'd

3 -2

(2.74 exp.)

(2.66 exp.)

(4.80 exp.)

5.40 1.18 6.22 1.98

(5.98 exp.)

6.91 2.18 6.93 2.65 9.90 2.22 5.54 2.20 6.04 2.95 6.04 3.13 7.74 2.36 7.70 1.52

0.98 2.60 2.50

3.84 2.50 4.08 5.11 C,lH,lO,P

CloH14N05PS 291.3 1.27 6.1 -3.22 4.30 5.31 3.81 CBHl,NO,PS 263.5 1.36 37.5 -2.70 4.00 5.10 3.00

C, ,H ,O,PS, 278.3 1.25 7.5 -2.70 3.74 5.35 4.10

C8Hlg02PS3 274.4 1.14 <25 -1.80 4.20 4.00 4.02