Estimation of Properties of Pure Organic Substances with Group and Pair Contributions

ABSTRACTbstract - This work presents a new predictive method for the estimation of properties of pure organic substances. Each compound is assigned a molecular graph or an adjacency matrix representing its chemical structure, from which properties are then obtained as a summation of all contributions associated with functional groups and chemically bonded pairs of groups. The proposed technique is applied to the estimation of critical temperature, critical pressure, critical volume and normal boiling point of 325 organic compounds from different chemical species. Accurate predictions based solely on chemical structure are obtained

Property estimation; group contribution; computer-aided molecular design

Authorship

J.E.S. Ourique

A. Silva Telles

SCIMAGO INSTITUTIONS RANKINGS

Figures | Tables

Figures (3)
Tables (10)

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Constant values (5) tc0 = 299.80 K (6) pc0 = 0.0951 bar-2 (7) vc0 = -139.9 cm3/mole (8) tb0 = 172.69 K

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Group g(T c ) g(P c )(x10 3 ) g(V c ) g(T b ) -CH3 45.41 21.5733 135.5 38.80 -CH2- 20.69 6.9280 36.1 19.69 >CH- -20.91 2.6407 -12.7 9.55 >C< -23.68 7.9654 -120.1 15.58 =CH2 4.21 14.9556 122.1 0.65 =CH- 22.80 7.7874 42.7 15.23 =C< 29.93 -29.1026 -29.8 6.30 -aCH= 46.50 7.7477 64.9 31.67 -aC= 22.10 -6.1067 -8.9 16.65 -O- 14.43 0.3343 9.6 8.74 -COOH 167.85 11.9399 127.3 130.29 -COO- 80.31 4.5626 41.4 71.78 HCOO- 91.66 10.9241 118.9 63.79 -CHO 86.78 15.0457 113.8 65.05 -CO- 48.61 1.5022 25.5 33.90 -NH2 67.79 5.6431 109.4 45.88 -NH- 19.97 -1.5613 20.2 14.14 >N- -2.02 -0.8156 -4.5 -0.70 -Cl 67.89 9.7172 110.4 40.95 -F -32.10 14.9068 91.2 -21.68 -Br 100.52 3.1409 115.2 58.17 -I 129.07 4.1283 125.2 76.82 -OH 84.86 3.6116 76.4 67.73 -cCH2- -0.42 1.2354 5.0 0.01 >cCH- 17.23 2.1042 13.3 13.08 >cC< 3.44 0.1719 0.7 2.31 -NO2 163.90 8.9546 130.5 114.07 -CN 138.82 20.3748 125.0 101.20 -S- 60.52 0.6705 33.4 41.16 -SH 93.15 5.0055 109.6 55.16

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Pair g(T c ) 12 g(P c ) 12 (x 10 3 ) g(V c ) 12 g(T b ) 12 -CH3,-CH3 -85.20 4.8951 16.8 -65.74 -CH3,-CH2- 13.02 2.2463 21.7 1.68 -CH3,>CH- 10.19 -1.3716 3.4 -4.12 -CH3,>C< 0.86 -4.6563 6.4 -10.92 -CH2-,-CH2- 1.92 2.4369 18.7 2.89 -CH2-,>CH- 9.48 -0.6649 -4.5 2.48 -CH2-,>C< 5.24 -7.3054 -5.8 -1.79 >CH-,>CH- 24.07 -5.2021 -30.3 4.52 >CH-,>C< 26.83 -13.7748 -31.7 5.02 >C<,>C< 59.16 -22.9345 -13.5 22.56 -CH3,=CH- -5.60 1.6201 3.0 -3.06 -CH3,=C< -6.28 14.4648 14.9 -1.34 -CH2-,=CH- 22.05 2.4892 9.8 20.86 -CH2-,=C< 5.70 5.0990 -14.3 11.71 >CH-,=CH- 12.27 0.1239 -16.6 8.47 >CH-,=C< 30.93 11.0865 -4.6 21.05 >C<,=CH- 20.85 -10.2021 7.5 11.14 =CH2,=CH2 -25.85 15.9563 24.8 -4.51 =CH2,=CH- 32.85 6.4359 24.8 24.42 =CH2,=C< 16.80 17.1688 16.3 19.52 =CH-,=CH- -0.64 0.3693 17.5 -3.88 =CH-,=C< -8.78 0.6129 -17.1 -1.43 =C<,=C< 7.82 -3.1613 -30.1 11.24 -CH3,aCH= 10.69 1.5762 0.8 6.25 -CH2-,aCH= -0.94 3.5120 8.2 6.83 >CH-,aCH= 3.27 -2.6943 -20.0 0.98 >C<,aCH= 9.09 -8.5006 2.1 2.59 -aCH=,-aCH= -1.74 0.4418 1.8 -0.66 -aCH=,-aC= -5.83 1.8822 0.6 -2.28 -aC=,-aC= -0.18 -0.3031 -6.4 -0.60 -CH3,-O- -2.96 -0.8854 14.6 -5.76 -CH2-,-O- 3.94 3.2083 8.2 7.48 >CH-,-O- 2.61 2.4436 -6.9 1.10 >C<,-O- 25.28 -4.0980 3.4 14.66 -CH3,-COOH 79.65 2.8496 48.1 49.27 -CH2-,-COOH 36.57 5.4158 43.5 37.88 >CH-,-COOH 51.62 3.6745 35.6 43.13 -CH3,-COO- 15.81 2.8506 27.2 3.36 -CH2-,-COO- 3.65 4.4468 24.5 2.39 >CH-,-COO- 3.39 -0.0462 7.6 -6.14 >C<,-COO- -11.48 -5.1980 19.0 -16.70 -CH3,HCOO- 50.34 1.5125 57.6 29.62 -CH2-,HCOO- 41.32 9.4116 61.3 34.17 -CH3,-CHO 29.01 2.5059 47.6 17.01 -CH2-,-CHO 33.26 8.4576 32.8 29.71 >CH-,-CHO 24.51 4.0822 33.3 18.33 -CH3,-CO- 35.68 3.3974 21.4 23.07

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Pair g(T c ) 12 g(P c ) 12 (x 10 3 ) g(V c ) 12 g(T b ) 12 -CH2-,-CO- 28.34 3.0729 27.1 24.55 >CH-,-CO- 33.19 -3.4660 2.5 20.18 -CH3,-NH2 17.05 -6.5242 49.0 9.45 -CH2-,-NH2 30.87 5.7240 36.6 27.27 >CH-,-NH2 18.69 4.5348 6.0 9.39 >C<,-NH2 1.17 1.9085 17.7 -0.24 -CH3,-NH- 13.53 0.2735 17.8 7.80 -CH2-,-NH- 15.04 -1.9679 18.9 14.27 >CH-,-NH- 11.36 -1.4282 3.7 6.20 -CH3,>N- -0.25 -0.7750 -2.7 -4.12 -CH2-,>N- -5.81 -1.6717 -11.0 2.01 -CH3,-Cl 3.14 -4.0385 33.0 -3.51 -CH2-,-Cl 41.98 5.8658 33.4 31.17 >CH-,-Cl 22.65 4.5421 19.6 13.84 >C<,-Cl 0.12 3.3478 24.4 -0.57 -CH3,-F 4.59 -1.1413 26.2 5.02 -CH2-,-F 35.55 -3.0703 6.4 25.98 >CH-,-F 38.77 0.4427 4.1 24.60 >C<,-F 31.16 0.1829 12.9 17.80 -CH3,-Br 21.27 -8.0171 45.2 7.05 -CH2-,-Br 42.56 3.3467 37.4 29.03 >CH-,-Br 36.70 7.8113 32.5 22.10 -CH3,-I 53.72 -4.3239 64.2 27.27 -CH2-,-I 75.36 8.4522 61.1 49.56 -CH2-,-OH 43.34 2.0742 29.4 28.98 >CH-,-OH 35.13 0.3002 14.3 22.83 >C<,-OH 6.40 1.2372 32.7 15.93 -CH3,>cCH- 4.35 0.6498 7.9 0.78 -CH3,>cC< 6.88 0.3439 1.5 4.62 -CH2-,>cCH- 12.88 1.4544 5.4 12.30 -cCH2-,-cCH2- 42.69 9.1617 69.9 30.20 -cCH2-,>cCH- 19.16 4.1235 28.8 14.13 -cCH2-,>cC< 6.88 0.3439 1.5 4.62 >cCH-,>cCH- 7.65 0.0424 -1.1 6.01 -CH3,-NO2 79.04 0.2287 47.4 48.79 -CH2-,-NO2 44.87 5.9245 50.7 37.56 >CH-,-NO2 40.00 2.8014 32.3 27.73 -CH3,-CN 61.47 6.7866 52.4 42.06 -CH2-,-CN 41.27 9.0314 44.8 35.18 >CH-,-CN 36.08 4.5569 27.8 23.96 -CH3,-S- 25.94 -2.2224 18.2 9.52 -CH3,-SH 31.59 -4.1162 39.8 12.45 -CH2-,-S- 10.24 0.6823 13.4 10.27 -CH2-,-SH 44.09 8.5422 32.3 35.72 >C<,-SH 17.46 0.5795 37.5 6.99 -S-,-S- 42.43 1.4405 17.6 31.26

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Tc Pc Vc Tb N AAEa AAPE N AAEb AAPE N AAEc AAPE N AAEa AAPE Joback and Reid 409 4.8 0.8 392 2.1 5.2 310 7.5 2.3 438 12.9 3.6 Constantinou and Gani 285 4.85 0.85 269 1.13 2.89 251 6.00 1.79 392 5.35 1.42 Proposed 325 8.09 1.50 325 0.95 2.51 325 6.36 1.69 325 5.50 1.50

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Functional class Average absolute percent error N Tc Pc Vc Tb C,H 128 1.48 2.26 1.83 1.51 C,H,O 105 1.30 1.59 1.38 1.35 C,H,N 30 1.21 2.40 1.72 1.00 C,H,X 46 2.36 5.68 2.22 2.33 C,H,S 12 1.19 1.80 1.15 1.19 C,H,O,N 4 0.44 1.05 0.27 0.35

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Method Tc Pc Vc Tb N AAEa AAPE AAEb AAPE AAEc AAPE AAEa AAPE Joback 65 16.15 2.72 4.64 15.42 68.72 17.06 34.86 8.80 Constantinou 61 42.41 7.66 3.92 13.70 66.70 16.06 35.85 9.31 Proposed 65 12.58 2.22 4.08 1.63 11.28 3.41 8.88 2.33

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Functional class AAPE N Method T c P c V c T b C,H 25 JR 1.31 8.39 9.26 4.17 25 CG 3.61 10.12 10.38 4.36 25 GPC 2.11 4.38 3.43 2.32 C,H,O 20 JR 3.99 20.99 21.74 9.79 20 CG 7.60 21.17 20.98 10.23 20 GPC 1.47 1.88 1.86 1.48 C,H,N 7 JR 3.92 29.22 19.31 11.46 6 CG 7.22 9.45 16.28 9.24 7 GPC 1.86 1.92 3.53 1.86 C,H,X 10 JR 2.32 11.62 23.56 14.13 8 CG 19.90 9.56 20.63 21.63 10 GPC 3.57 8.91 4.28 3.61 C,H,S 2 JR 2.50 19.10 8.93 6.69 2 CG 11.16 13.17 18.82 12.94 2 GPC 5.93 5.65 15.00 6.80 C,H,O,N 1 JR 8.59 13.80 53.60 37.22 0 CG - - - - 1 GPC 1.76 4.31 1.17 1.39

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Properties Subgraph(s) T c P c V c T b Total contribution (number of occurrences times contribution) -aCH= [1],[2],[4],[5], [6],[8],[9], [10],[11], [12] 465.00 77.477x10-3 649.0 316.70 -aC= [3], [7] 44.20 -12.213x10-3 -18.0 33.30 Group summation 509.20 65.264x10-3 631.0 350.00 -aCH=,-aCH= [1,2],[4,5], [5,6],[1,6], [8,9],[9,10], [10,11],[11,12] -13.92 3.534x10-3 14.4 -5.28 -aCH=,-aC= [2,3],[3,4], [7,8],[8,12] -23.32 7.529x10-3 2.4 -9.12 -aC=,-aC= [3,7] -0.18 -0.303x10-3 -6.4 -0.60 Pair summation -37.42 10.760x10-3 10.4 -15.00 Proposed method Equation 5 Equation 6 Equation 7 Equation 8 Calculated Value 771.58 K 34.15 bar 501.6 cm3/mole 507.69 K Literature Value 789 K 38.5 bar 502 cm3/mole 529.3 K Abs. error (%) -2.21 -11.30 -0.08 -4.08 Joback and Reid Calculated Value 780.11 K 34.28 bar 491.5 cm3/mole 527.52 K Abs. error (%) 1.13 10.96 2.09 0.34 Constantinou and Gani Calculated Value 663.73 K 32.18 bar 449.9 cm3/mole 464.08 K Abs. error (%) 15.88 16.41 10.38 12.32

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Properties Subgraph(s) T c P c V c T b Total contribution (number of occurrences times contribution) -CH3 [4] 45.41 21.5733x10-3 135.5 38.80 -CH2- [1], [2] 41.39 13.8561x10-3 72.2 39.37 >CH- [3] -20.91 2.6407x10-3 -12.7 9.55 -OH [5], [6] 169.73 7.2231x10-3 152.8 135.46 Group summation 235.62 45.2932x10-3 347.8 223.18 -CH3,>CH- [3,4] 10.19 -1.3712x10-3 3.4 -4.12 -CH2-,-CH2- [1,2] 1.92 2.4369x10-3 18.7 2.89 -CH2-,>CH- [2,3] 9.48 -0.6649x10-3 -4.5 2.48 -CH2-,-OH [1,5] 43.34 2.0742x10-3 29.4 28.98 >CH-,-OH [3,6] 35.13 0.3002x10-3 14.3 22.83 Pair summation 100.06 2.7748x10-3 61.3 53.06 Proposed method Equation 5 Equation 6 Equation 7 Equation 8 Calculated Value 635.48 K 48.78 bar 269.2 cm3/mole 448.93 K Literature Value 643 K 50 bar 292 cm3/mole 480.15 K Abs. error (%) 1.17 2.43 7.81 6.50 Joback and Reid Calculated Value 643.59 K 50.30 bar 291.5 cm3/mole 475.04 K Abs. error (%) 0.09 0.60 0.50 1.06 Constantinou and Gani Calculated Value 628.61 K 44.17 bar 291.7 cm3/mole 465.76 K Abs. error (%) 2.24 11.66 0.11 3.00

Constant values
(5)	t_c0 = 299.80 K
(6)	p_c0 = 0.0951 bar^-2
(7)	v_c0 = -139.9 cm³/mole
(8)	t_b0 = 172.69 K

Group	g(T _c )	g(P _c )(x10 ³ )	g(V _c )	g(T _b )
-CH₃	45.41	21.5733	135.5	38.80
-CH₂-	20.69	6.9280	36.1	19.69
>CH-	-20.91	2.6407	-12.7	9.55
>C<	-23.68	7.9654	-120.1	15.58
=CH₂	4.21	14.9556	122.1	0.65
=CH-	22.80	7.7874	42.7	15.23
=C<	29.93	-29.1026	-29.8	6.30
-aCH=	46.50	7.7477	64.9	31.67
-aC=	22.10	-6.1067	-8.9	16.65
-O-	14.43	0.3343	9.6	8.74
-COOH	167.85	11.9399	127.3	130.29
-COO-	80.31	4.5626	41.4	71.78
HCOO-	91.66	10.9241	118.9	63.79
-CHO	86.78	15.0457	113.8	65.05
-CO-	48.61	1.5022	25.5	33.90
-NH₂	67.79	5.6431	109.4	45.88
-NH-	19.97	-1.5613	20.2	14.14
>N-	-2.02	-0.8156	-4.5	-0.70
-Cl	67.89	9.7172	110.4	40.95
-F	-32.10	14.9068	91.2	-21.68
-Br	100.52	3.1409	115.2	58.17
-I	129.07	4.1283	125.2	76.82
-OH	84.86	3.6116	76.4	67.73
-cCH₂-	-0.42	1.2354	5.0	0.01
>cCH-	17.23	2.1042	13.3	13.08
>cC<	3.44	0.1719	0.7	2.31
-NO₂	163.90	8.9546	130.5	114.07
-CN	138.82	20.3748	125.0	101.20
-S-	60.52	0.6705	33.4	41.16
-SH	93.15	5.0055	109.6	55.16

Pair	g(T _c ) ₁₂	g(P _c ) ₁₂ (x 10 ³ )	g(V _c ) ₁₂	g(T _b ) ₁₂
-CH₃,-CH₃	-85.20	4.8951	16.8	-65.74
-CH₃,-CH₂-	13.02	2.2463	21.7	1.68
-CH₃,>CH-	10.19	-1.3716	3.4	-4.12
-CH₃,>C<	0.86	-4.6563	6.4	-10.92
-CH₂-,-CH₂-	1.92	2.4369	18.7	2.89
-CH₂-,>CH-	9.48	-0.6649	-4.5	2.48
-CH₂-,>C<	5.24	-7.3054	-5.8	-1.79
>CH-,>CH-	24.07	-5.2021	-30.3	4.52
>CH-,>C<	26.83	-13.7748	-31.7	5.02
>C<,>C<	59.16	-22.9345	-13.5	22.56
-CH₃,=CH-	-5.60	1.6201	3.0	-3.06
-CH₃,=C<	-6.28	14.4648	14.9	-1.34
-CH₂-,=CH-	22.05	2.4892	9.8	20.86
-CH₂-,=C<	5.70	5.0990	-14.3	11.71
>CH-,=CH-	12.27	0.1239	-16.6	8.47
>CH-,=C<	30.93	11.0865	-4.6	21.05
>C<,=CH-	20.85	-10.2021	7.5	11.14
=CH₂,=CH₂	-25.85	15.9563	24.8	-4.51
=CH₂,=CH-	32.85	6.4359	24.8	24.42
=CH₂,=C<	16.80	17.1688	16.3	19.52
=CH-,=CH-	-0.64	0.3693	17.5	-3.88
=CH-,=C<	-8.78	0.6129	-17.1	-1.43
=C<,=C<	7.82	-3.1613	-30.1	11.24
-CH₃,aCH=	10.69	1.5762	0.8	6.25
-CH₂-,aCH=	-0.94	3.5120	8.2	6.83
>CH-,aCH=	3.27	-2.6943	-20.0	0.98
>C<,aCH=	9.09	-8.5006	2.1	2.59
-aCH=,-aCH=	-1.74	0.4418	1.8	-0.66
-aCH=,-aC=	-5.83	1.8822	0.6	-2.28
-aC=,-aC=	-0.18	-0.3031	-6.4	-0.60
-CH₃,-O-	-2.96	-0.8854	14.6	-5.76
-CH₂-,-O-	3.94	3.2083	8.2	7.48
>CH-,-O-	2.61	2.4436	-6.9	1.10
>C<,-O-	25.28	-4.0980	3.4	14.66
-CH₃,-COOH	79.65	2.8496	48.1	49.27
-CH₂-,-COOH	36.57	5.4158	43.5	37.88
>CH-,-COOH	51.62	3.6745	35.6	43.13
-CH₃,-COO-	15.81	2.8506	27.2	3.36
-CH₂-,-COO-	3.65	4.4468	24.5	2.39
>CH-,-COO-	3.39	-0.0462	7.6	-6.14
>C<,-COO-	-11.48	-5.1980	19.0	-16.70
-CH₃,HCOO-	50.34	1.5125	57.6	29.62
-CH₂-,HCOO-	41.32	9.4116	61.3	34.17
-CH₃,-CHO	29.01	2.5059	47.6	17.01
-CH₂-,-CHO	33.26	8.4576	32.8	29.71
>CH-,-CHO	24.51	4.0822	33.3	18.33
-CH₃,-CO-	35.68	3.3974	21.4	23.07

Pair	g(T _c ) ₁₂	g(P _c ) ₁₂ (x 10 ³ )	g(V _c ) ₁₂	g(T _b ) ₁₂
-CH₂-,-CO-	28.34	3.0729	27.1	24.55
>CH-,-CO-	33.19	-3.4660	2.5	20.18
-CH₃,-NH₂	17.05	-6.5242	49.0	9.45
-CH₂-,-NH₂	30.87	5.7240	36.6	27.27
>CH-,-NH₂	18.69	4.5348	6.0	9.39
>C<,-NH₂	1.17	1.9085	17.7	-0.24
-CH₃,-NH-	13.53	0.2735	17.8	7.80
-CH₂-,-NH-	15.04	-1.9679	18.9	14.27
>CH-,-NH-	11.36	-1.4282	3.7	6.20
-CH₃,>N-	-0.25	-0.7750	-2.7	-4.12
-CH₂-,>N-	-5.81	-1.6717	-11.0	2.01
-CH₃,-Cl	3.14	-4.0385	33.0	-3.51
-CH₂-,-Cl	41.98	5.8658	33.4	31.17
>CH-,-Cl	22.65	4.5421	19.6	13.84
>C<,-Cl	0.12	3.3478	24.4	-0.57
-CH₃,-F	4.59	-1.1413	26.2	5.02
-CH₂-,-F	35.55	-3.0703	6.4	25.98
>CH-,-F	38.77	0.4427	4.1	24.60
>C<,-F	31.16	0.1829	12.9	17.80
-CH₃,-Br	21.27	-8.0171	45.2	7.05
-CH₂-,-Br	42.56	3.3467	37.4	29.03
>CH-,-Br	36.70	7.8113	32.5	22.10
-CH₃,-I	53.72	-4.3239	64.2	27.27
-CH₂-,-I	75.36	8.4522	61.1	49.56
-CH₂-,-OH	43.34	2.0742	29.4	28.98
>CH-,-OH	35.13	0.3002	14.3	22.83
>C<,-OH	6.40	1.2372	32.7	15.93
-CH₃,>cCH-	4.35	0.6498	7.9	0.78
-CH₃,>cC<	6.88	0.3439	1.5	4.62
-CH₂-,>cCH-	12.88	1.4544	5.4	12.30
-cCH₂-,-cCH₂-	42.69	9.1617	69.9	30.20
-cCH₂-,>cCH-	19.16	4.1235	28.8	14.13
-cCH₂-,>cC<	6.88	0.3439	1.5	4.62
>cCH-,>cCH-	7.65	0.0424	-1.1	6.01
-CH₃,-NO₂	79.04	0.2287	47.4	48.79
-CH₂-,-NO₂	44.87	5.9245	50.7	37.56
>CH-,-NO₂	40.00	2.8014	32.3	27.73
-CH₃,-CN	61.47	6.7866	52.4	42.06
-CH₂-,-CN	41.27	9.0314	44.8	35.18
>CH-,-CN	36.08	4.5569	27.8	23.96
-CH₃,-S-	25.94	-2.2224	18.2	9.52
-CH₃,-SH	31.59	-4.1162	39.8	12.45
-CH₂-,-S-	10.24	0.6823	13.4	10.27
-CH₂-,-SH	44.09	8.5422	32.3	35.72
>C<,-SH	17.46	0.5795	37.5	6.99
-S-,-S-	42.43	1.4405	17.6	31.26

	T_c				P_c			V_c			T_b
	N	AAE^a	AAPE	N	AAE^b	AAPE	N	AAE^c	AAPE	N	AAE^a	AAPE
Joback and Reid	409	4.8	0.8	392	2.1	5.2	310	7.5	2.3	438	12.9	3.6
Constantinou and Gani	285	4.85	0.85	269	1.13	2.89	251	6.00	1.79	392	5.35	1.42
Proposed	325	8.09	1.50	325	0.95	2.51	325	6.36	1.69	325	5.50	1.50

Functional class	Average absolute percent error
Functional class	N	T_c	P_c	V_c	T_b
C,H	128	1.48	2.26	1.83	1.51
C,H,O	105	1.30	1.59	1.38	1.35
C,H,N	30	1.21	2.40	1.72	1.00
C,H,X	46	2.36	5.68	2.22	2.33
C,H,S	12	1.19	1.80	1.15	1.19
C,H,O,N	4	0.44	1.05	0.27	0.35

Method	T_c			P_c		V_c		T_b
Method	N	AAE^a	AAPE	AAE^b	AAPE	AAE^c	AAPE	AAE^a	AAPE
Joback	65	16.15	2.72	4.64	15.42	68.72	17.06	34.86	8.80
Constantinou	61	42.41	7.66	3.92	13.70	66.70	16.06	35.85	9.31
Proposed	65	12.58	2.22	4.08	1.63	11.28	3.41	8.88	2.33

Functional class	AAPE
Functional class	N	Method	T _c	P _c	V _c	T _b
C,H	25	JR	1.31	8.39	9.26	4.17
	25	CG	3.61	10.12	10.38	4.36
	25	GPC	2.11	4.38	3.43	2.32
C,H,O	20	JR	3.99	20.99	21.74	9.79
	20	CG	7.60	21.17	20.98	10.23
	20	GPC	1.47	1.88	1.86	1.48
C,H,N	7	JR	3.92	29.22	19.31	11.46
	6	CG	7.22	9.45	16.28	9.24
	7	GPC	1.86	1.92	3.53	1.86
C,H,X	10	JR	2.32	11.62	23.56	14.13
	8	CG	19.90	9.56	20.63	21.63
	10	GPC	3.57	8.91	4.28	3.61
C,H,S	2	JR	2.50	19.10	8.93	6.69
	2	CG	11.16	13.17	18.82	12.94
	2	GPC	5.93	5.65	15.00	6.80
C,H,O,N	1	JR	8.59	13.80	53.60	37.22
	0	CG	-	-	-	-
	1	GPC	1.76	4.31	1.17	1.39

	Properties
	Subgraph(s)	T _c	P _c	V _c	T _b
	Subgraph(s)	Total contribution (number of occurrences times contribution)
-aCH=	[1],[2],[4],[5], [6],[8],[9], [10],[11], [12]	465.00	77.477x10^-3	649.0	316.70
-aC=	[3], [7]	44.20	-12.213x10^-3	-18.0	33.30
Group summation		509.20	65.264x10^-3	631.0	350.00
-aCH=,-aCH=	[1,2],[4,5], [5,6],[1,6], [8,9],[9,10], [10,11],[11,12]	-13.92	3.534x10^-3	14.4	-5.28
-aCH=,-aC=	[2,3],[3,4], [7,8],[8,12]	-23.32	7.529x10^-3	2.4	-9.12
-aC=,-aC=	[3,7]	-0.18	-0.303x10^-3	-6.4	-0.60
Pair summation		-37.42	10.760x10^-3	10.4	-15.00
Proposed method		Equation 5	Equation 6	Equation 7	Equation 8
Calculated Value		771.58 K	34.15 bar	501.6 cm³/mole	507.69 K
Literature Value		789 K	38.5 bar	502 cm³/mole	529.3 K
Abs. error (%)		-2.21	-11.30	-0.08	-4.08
Joback and Reid
Calculated Value		780.11 K	34.28 bar	491.5 cm³/mole	527.52 K
Abs. error (%)		1.13	10.96	2.09	0.34
Constantinou and Gani
Calculated Value		663.73 K	32.18 bar	449.9 cm³/mole	464.08 K
Abs. error (%)		15.88	16.41	10.38	12.32

	Properties
	Subgraph(s)	T _c	P _c	V _c	T _b
	Subgraph(s)	Total contribution (number of occurrences times contribution)
-CH3	[4]	45.41	21.5733x10^-3	135.5	38.80
-CH2-	[1], [2]	41.39	13.8561x10^-3	72.2	39.37
>CH-	[3]	-20.91	2.6407x10^-3	-12.7	9.55
-OH	[5], [6]	169.73	7.2231x10^-3	152.8	135.46
Group summation		235.62	45.2932x10^-3	347.8	223.18
-CH3,>CH-	[3,4]	10.19	-1.3712x10^-3	3.4	-4.12
-CH2-,-CH2-	[1,2]	1.92	2.4369x10^-3	18.7	2.89
-CH2-,>CH-	[2,3]	9.48	-0.6649x10^-3	-4.5	2.48
-CH2-,-OH	[1,5]	43.34	2.0742x10^-3	29.4	28.98
>CH-,-OH	[3,6]	35.13	0.3002x10^-3	14.3	22.83
Pair summation		100.06	2.7748x10^-3	61.3	53.06
Proposed method		Equation 5	Equation 6	Equation 7	Equation 8
Calculated Value		635.48 K	48.78 bar	269.2 cm³/mole	448.93 K
Literature Value		643 K	50 bar	292 cm³/mole	480.15 K
Abs. error (%)		1.17	2.43	7.81	6.50
Joback and Reid
Calculated Value		643.59 K	50.30 bar	291.5 cm³/mole	475.04 K
Abs. error (%)		0.09	0.60	0.50	1.06
Constantinou and Gani
Calculated Value		628.61 K	44.17 bar	291.7 cm³/mole	465.76 K
Abs. error (%)		2.24	11.66	0.11	3.00

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Estimation of Properties of Pure Organic Substances with Group and Pair Contributions

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