Calculation of the Isobaric Heat Capacities of the Liquid and Solid Phase of Organic Compounds at 298.15K by Means of the Group-Additivity Method
Abstract
:1. Introduction
2. Method
3. Sources of Heat-Capacity Data
4. Results
4.1. General Remarks
- In the subsequent figures, the results of the cross-validation calculations have been superimposed in red over the training data drawn in black.
- The complete lists of compounds with known heat capacities used in this study are available as SDF files in the Supplementary Materials, downloadable by external chemistry software. In addition, the Supplementary Materials provides the results lists containing the molecules’ names and experimental, training, and cross-validation data. Beyond this, the lists of outliers of both heat-capacity calculations are also available in the Supplementary Materials.
4.2. Heat Capacity of Liquids
4.3. Heat Capacity of Solids
5. Conclusions
Supplementary Materials
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
- GA: atom-group additivity
- Vm: "true" molecular volume
References
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Sample Availability: Samples of the compounds are not available. |
Atom Type | Neighbours | Meaninga | Example |
---|---|---|---|
B(-) | F4 | BF4- | tetrafluoroborate |
C sp3 | H2CN(+) | CCH2N(+) | C1 in tetraalkylammonium |
C sp3 | H2CP(+) | CCH2P(+) | C1 in tetraalkylphosphonium |
C sp3 | H2CS(+) | CCH2S(+) | C1 in trialkylsulfonium |
C(-) sp3 | C3 | C3C- | central C- in tricyanocarbeniate |
C aromatic | H:C:N(+) | C:CH:N+ | C2 in pyridinium |
C(+) aromatic | H:N2 | N:C+H:N | C2 in imidazolium |
C sp | B#N(-) | B-(C#N) | C in tetracyanoborate |
C sp | C#N(-) | C-(C#N) | cyano-C in tricyanocarbeniate |
C sp | N#N(-) | N-(C#N) | C in dicyanoamide |
C sp | =N=S(-) | N=C=S- | thiocyanate |
N(+) sp3 | C4 | N+C4 | tetraalkylammonium |
N(+) sp2 | O2=O(-) | NO3- | nitrate |
N aromatic | C2:C(+) | C-N(C):C+ | N1 and N3 in 1,3-dialkylimidazolium |
N(+) aromatic | C:C2 | C:N+(C):C | N in 1-alkylpyridinium |
N(-) | C2 | C-N--C | N- in dicyanoamide |
N(-) | CS | C-N--S | N- in saccharinate |
N(-) | S2 | S-N--S | bis(trifluoromethanesulfonyl)amide |
P4 | CO2=O(-) | CPO3- | alkylphosphonate |
P(+) | C4 | PC4+ | tetraalkylphosphonium |
P(-) | C3F3 | F3P-C3 | tris(pentafluoroethyl)trifluorophosphate |
P(-) | F6 | PF6- | hexafluorophosphate |
S(+) | C3 | C3S+ | trialkylsulfonium |
S4 | CN=O2(-) | CS(O2)N- | bis(trifluoromethanesulfonyl)amide |
S4 | CO=O2(-) | CSO3- | alkylsulfonate |
S4 | O2=O2(-) | SO4- | alkylsulfate |
Atom Type | Neighbours | Meaning |
---|---|---|
O(prim) | HC | Primary alcohol |
O(sec) | HC | Secondary alcohol |
O(tert) | HC | Tertiary alcohol |
Endocyclic bonds | No of single bonds | Count single bonds in cyclic ring |
Angle60 | Bond angle < 60 deg | |
Angle 90 | Bond angle between 60 and 90 deg | |
Angle102 | Bond angle between 90 and 102 deg | |
(COH)n | n > 1 | Molecule contains more than 1 OH group |
H | H Acceptor | Intramolecular H bridge between acidic H (on O, N or S) and basic acceptor (O, N or F) |
Entry | Atom Type | Neighbours | Contribution | Occurrences | Molecules |
---|---|---|---|---|---|
1 | B | C3 | 240 | 1 | 1 |
2 | B(-) | C4 | 698.66 | 2 | 2 |
3 | B(-) | F4 | 51.21 | 6 | 6 |
4 | C sp3 | H3C | 37.03 | 1555 | 790 |
5 | C sp3 | H3N | 100.02 | 127 | 101 |
6 | C sp3 | H3N(+) | 147.91 | 20 | 18 |
7 | C sp3 | H3O | 81.29 | 84 | 66 |
8 | C sp3 | H3S | 84.43 | 17 | 13 |
9 | C sp3 | H3S(+) | 172.17 | 1 | 1 |
10 | C sp3 | H3P | 217.59 | 1 | 1 |
11 | C sp3 | H3Si | 71 | 71 | 18 |
12 | C sp3 | H2BC | –37.03 | 3 | 1 |
13 | C sp3 | H2C2 | 30.06 | 3249 | 696 |
14 | C sp3 | H2CN | 90.52 | 222 | 146 |
15 | C sp3 | H2CN(+) | 142.85 | 78 | 52 |
16 | C sp3 | H2CO | 73.86 | 477 | 243 |
17 | C sp3 | H2CS | 75.25 | 38 | 27 |
18 | C sp3 | H2CS(+) | 136.25 | 29 | 10 |
19 | C sp3 | H2CP | 252.08 | 2 | 1 |
20 | C sp3 | H2CP(+) | 71.8 | 12 | 3 |
21 | C sp3 | H2CCl | 63.67 | 38 | 30 |
22 | C sp3 | H2CBr | 63.93 | 26 | 21 |
23 | C sp3 | H2CJ | 67.73 | 10 | 9 |
24 | C sp3 | H2CSi | 60.71 | 18 | 8 |
25 | C sp3 | H2N2 | 151.55 | 4 | 2 |
26 | C sp3 | H2NO | 157.51 | 12 | 12 |
27 | C sp3 | H2O2 | 111.47 | 4 | 4 |
28 | C sp3 | H2S2 | 128.41 | 1 | 1 |
29 | C sp3 | HC3 | 21.11 | 303 | 196 |
30 | C sp3 | HC2N | 81.86 | 14 | 14 |
31 | C sp3 | HC2N(+) | 159.6 | 3 | 3 |
32 | C sp3 | HC2O | 67.45 | 107 | 87 |
33 | C sp3 | HC2S | 67.46 | 10 | 9 |
34 | C sp3 | HC2Si | 36.48 | 1 | 1 |
35 | C sp3 | HC2Cl | 56.56 | 9 | 9 |
36 | C sp3 | HC2Br | 56.84 | 4 | 4 |
37 | C sp3 | HC2J | 62.21 | 2 | 2 |
38 | C sp3 | HCNO(+) | 176.8 | 3 | 1 |
39 | C sp3 | HCO2 | 96.7 | 3 | 3 |
40 | C sp3 | HCF2 | 157.26 | 1 | 1 |
41 | C sp3 | HCFCl | 73.89 | 1 | 1 |
42 | C sp3 | HCCl2 | 86.15 | 9 | 8 |
43 | C sp3 | HCClBr | 89.68 | 1 | 1 |
44 | C sp3 | HCBr2 | 82.85 | 2 | 1 |
45 | C sp3 | C4 | 7.78 | 62 | 51 |
46 | C sp3 | C3N | 81.33 | 5 | 4 |
47 | C sp3 | C3N(+) | 55.23 | 3 | 3 |
48 | C sp3 | C3O | 57.44 | 23 | 21 |
49 | C sp3 | C3S | 57.43 | 7 | 5 |
50 | C sp3 | C3F | 43.66 | 5 | 3 |
51 | C sp3 | C3Cl | 50.92 | 1 | 1 |
52 | C sp3 | C3Br | 54.62 | 1 | 1 |
53 | C sp3 | C2N2(+) | 223.66 | 2 | 2 |
54 | C sp3 | C2O2 | 99.71 | 1 | 1 |
55 | C sp3 | C2F2 | 50.88 | 78 | 13 |
56 | C sp3 | C2FCl | 64.31 | 5 | 2 |
57 | C sp3 | C2Cl2 | 87.42 | 2 | 2 |
58 | C sp3 | CNF2 | 112.99 | 3 | 1 |
59 | C sp3 | CF3 | 66.92 | 31 | 23 |
60 | C sp3 | CSF2 | 0 | 1 | 1 |
61 | C sp3 | CPF2(-) | 44.23 | 6 | 2 |
62 | C sp3 | CF2Cl | 89.67 | 4 | 4 |
63 | C sp3 | CF2Br | 86.41 | 7 | 4 |
64 | C sp3 | CFCl2 | 88.11 | 3 | 2 |
65 | C sp3 | CCl3 | 102.55 | 8 | 8 |
66 | C sp3 | SF3 | 102.78 | 151 | 78 |
67 | C(-) sp3 | C3 | 131.76 | 1 | 1 |
68 | C sp2 | H2=C | 35.64 | 61 | 59 |
69 | C sp2 | HC=C | 22.79 | 195 | 107 |
70 | C sp2 | HC=N | 95.94 | 4 | 4 |
71 | C sp2 | HC=O | 54.97 | 23 | 23 |
72 | C sp2 | H=CN | 92.25 | 166 | 87 |
73 | C sp2 | H=CO | 42.8 | 11 | 10 |
74 | C sp2 | H=CS | 87.41 | 5 | 5 |
75 | C sp2 | H=CCl | 56.41 | 5 | 3 |
76 | C sp2 | H=CSi | 43.69 | 4 | 4 |
77 | C sp2 | HN=N | 32.91 | 3 | 3 |
78 | C sp2 | HN=O | 100.63 | 3 | 3 |
79 | C sp2 | HO=O | 58.82 | 7 | 7 |
80 | C sp2 | H=NS | 15.48 | 2 | 2 |
81 | C sp2 | C2=C | 16.22 | 54 | 44 |
82 | C sp2 | C2=N | 333.48 | 1 | 1 |
83 | C sp2 | C=CN | 89.61 | 3 | 2 |
84 | C sp2 | C2=O | 50.28 | 49 | 49 |
85 | C sp2 | C=CO | 36.16 | 5 | 5 |
86 | C sp2 | C=CS | 74.31 | 5 | 4 |
87 | C sp2 | C=CCl | 160.28 | 1 | 1 |
88 | C sp2 | CN=O | 87.09 | 12 | 12 |
89 | C sp2 | CN=O(-) | 87.78 | 1 | 1 |
90 | C sp2 | C=NS | 8.06 | 1 | 1 |
91 | C sp2 | CO=O | 43.25 | 216 | 158 |
92 | C sp2 | CO=O(-) | 27.63 | 8 | 7 |
93 | C sp2 | C=OS | 0 | 1 | 1 |
94 | C sp2 | C=OCl | 70.53 | 7 | 6 |
95 | C sp2 | =CF2 | 56.5 | 2 | 1 |
96 | C sp2 | =CCl2 | 77.26 | 5 | 4 |
97 | C sp2 | N2=N | 56.88 | 1 | 1 |
98 | C sp2 | N2=O | 131.83 | 3 | 3 |
99 | C sp2 | NO=O | 98.32 | 1 | 1 |
100 | C sp2 | O2=O | 50.04 | 5 | 5 |
101 | C aromatic | H:C2 | 22 | 1115 | 238 |
102 | C aromatic | H:C:N | 42.32 | 19 | 13 |
103 | C aromatic | H:C:N(+) | –9.45 | 53 | 32 |
104 | C aromatic | H:N2 | 0 | 0 | |
105 | C aromatic | :C3 | 9.57 | 19 | 11 |
106 | C aromatic | C:C2 | 11.58 | 251 | 152 |
107 | C aromatic | C:C:N | 30.59 | 8 | 7 |
108 | C aromatic | C:C:N(+) | –2.69 | 11 | 11 |
109 | C aromatic | :C2N | 71.34 | 31 | 29 |
110 | C aromatic | :C2N(+) | 118.05 | 11 | 8 |
111 | C aromatic | :C2:N | 31.72 | 3 | 3 |
112 | C aromatic | :C2O | 33.82 | 46 | 28 |
113 | C aromatic | :C2S | 88.68 | 7 | 7 |
114 | C aromatic | :C2Si | 37.2 | 10 | 7 |
115 | C aromatic | :C2F | 37.06 | 54 | 17 |
116 | C aromatic | :C2Cl | 41.28 | 19 | 15 |
117 | C aromatic | :C2Br | 52.57 | 11 | 8 |
118 | C aromatic | :C2J | 43.43 | 3 | 3 |
119 | C(+) aromatic | H:N2 | –155.06 | 74 | 74 |
120 | C sp | B#N(-) | –130.93 | 8 | 2 |
121 | C sp | H#C | 38.78 | 6 | 5 |
122 | C sp | C#C | 23.99 | 10 | 7 |
123 | C sp | =C2 | 25.16 | 4 | 4 |
124 | C sp | C#N | 48.78 | 35 | 31 |
125 | C sp | C#N(-) | –9.81 | 3 | 1 |
126 | C sp | #CSi | 49.58 | 2 | 1 |
127 | C sp | N#N(-) | –2.88 | 12 | 6 |
128 | C sp | =N2 | –89.69 | 1 | 1 |
129 | C sp | =N=O | –20.75 | 8 | 5 |
130 | C sp | =N=S(-) | 43.63 | 3 | 3 |
131 | N sp3 | H2C | –4.35 | 33 | 28 |
132 | N sp3 | H2C(pi) | 0.31 | 9 | 9 |
133 | N sp3 | H2N | 48.67 | 5 | 4 |
134 | N sp3 | HC2 | –71.79 | 21 | 20 |
135 | N sp3 | HC2(pi) | –72.44 | 14 | 14 |
136 | N sp3 | HC2(2pi) | –103.28 | 6 | 6 |
137 | N sp3 | HCN | –15.74 | 4 | 3 |
138 | N sp3 | HCN(pi) | –13 | 1 | 1 |
139 | N sp3 | HCS(pi) | –21.52 | 1 | 1 |
140 | N sp3 | C3 | –160.23 | 33 | 28 |
141 | N sp3 | C3(pi) | –149.65 | 17 | 14 |
142 | N sp3 | C3(2pi) | –180.02 | 3 | 3 |
143 | N sp3 | C3(3pi) | –165.46 | 1 | 1 |
144 | N sp3 | C2N | –91.6 | 2 | 2 |
145 | N sp3 | C2N(2pi) | –143.37 | 2 | 2 |
146 | N sp3 | C2N(3pi) | –160.71 | 1 | 1 |
147 | N sp2 | H=C | –243.13 | 1 | 1 |
148 | N sp2 | C=C | 15.82 | 17 | 13 |
149 | N sp2 | C=N | –20.24 | 2 | 1 |
150 | N sp2 | C=N(+) | –42.22 | 1 | 1 |
151 | N sp2 | =CN | 0 | 3 | 3 |
152 | N sp2 | =CO | –53.43 | 1 | 1 |
153 | N aromatic | C2:C(+) | –0.31 | 148 | 74 |
154 | N aromatic | :C2 | −16.75 | 15 | 15 |
155 | N(+) sp3 | H3C | −44.33 | 1 | 1 |
156 | N(+) sp3 | H2C2 | −140.41 | 4 | 4 |
157 | N(+) sp3 | HC3 | −291.64 | 1 | 1 |
158 | N(+) sp3 | C4 | −372.93 | 13 | 13 |
159 | N(+) sp2 | C=NO(-) | 0 | 1 | 1 |
160 | N(+) sp2 | CO=O(-) | −45.71 | 25 | 17 |
161 | N(+) sp2 | O2=O(-) | 5.99 | 4 | 4 |
162 | N(+) aromatic | C:C2 | 14.22 | 32 | 32 |
163 | N(-) | C2 | 62.36 | 6 | 6 |
164 | N(-) | CS | −32.57 | 1 | 1 |
165 | N(-) | S2 | 33.36 | 73 | 73 |
166 | O(prim) | HC | 14.35 | 102 | 89 |
167 | O(sec) | HC | 36.17 | 47 | 47 |
168 | O(tert) | HC | 58 | 11 | 11 |
169 | O | HC(pi) | 48.39 | 57 | 46 |
170 | O | HP | −119.34 | 1 | 1 |
171 | O | HS | 39.11 | 1 | 1 |
172 | O | C2 | −59.32 | 170 | 98 |
173 | O | C2(pi) | −26.57 | 191 | 149 |
174 | O | C2(2pi) | −15.47 | 22 | 12 |
175 | O | CN(+)(pi) | 55.55 | 3 | 3 |
176 | O | CN(2pi) | 0 | 1 | 1 |
177 | O | CS | 16.03 | 8 | 8 |
178 | O | CP(pi) | 22.25 | 3 | 1 |
179 | O | CSi | −22.04 | 20 | 5 |
180 | O | Si2 | −21.83 | 19 | 7 |
181 | P4 | C2O=O(-) | −344.96 | 1 | 1 |
182 | P4 | CO2=O(-) | 0 | 1 | 1 |
183 | P4 | O3=O | 0 | 1 | 1 |
184 | P(+) | C4 | −95.06 | 3 | 3 |
185 | P(-) | C3F3 | 33.12 | 2 | 2 |
186 | P(-) | F6 | 96.53 | 9 | 9 |
187 | S2 | HC | 0.94 | 19 | 19 |
188 | S2 | HC(pi) | −25.44 | 1 | 1 |
189 | S2 | C2 | −53.94 | 19 | 19 |
190 | S2 | C2(pi) | −77.07 | 2 | 2 |
191 | S2 | C2(2pi) | −89.86 | 7 | 7 |
192 | S2 | CS | −11.11 | 8 | 4 |
193 | S4 | C2=O | −23.45 | 2 | 2 |
194 | S4 | C2=O2 | −18.86 | 1 | 1 |
195 | S4 | CN=O2 | 0 | 1 | 1 |
196 | S4 | CN=O2(-) | 5.69 | 147 | 74 |
197 | S4 | CO=O2(-) | 4.61 | 9 | 9 |
198 | S4 | O2=O2(-) | 0 | 9 | 9 |
199 | S(+) | C3 | −203.28 | 10 | 10 |
200 | Si | C4 | −89.09 | 11 | 10 |
201 | Si | C3O | −49.41 | 6 | 3 |
202 | Si | C3Cl | −25.49 | 1 | 1 |
203 | Si | C2O2 | 9.5 | 16 | 6 |
204 | Si | C2Cl2 | 25.44 | 3 | 3 |
205 | Si | CCl3 | 86.83 | 3 | 3 |
206 | Si | O4 | 0 | 5 | 5 |
207 | (COH)n | n > 1 | −27.73 | 20 | 19 |
208 | H | H Acceptor | −21.43 | 3 | 3 |
209 | Endocyclic bonds | No of single bds | −3.92 | 1341 | 243 |
210 | Angle60 | 4.13 | 69 | 19 | |
211 | Angle90 | 1.7 | 63 | 19 | |
A | Based on | Valid groups | 134 | 1176 | |
B | Goodness of fit | R2 | 0.998 | 1111 | |
C | Deviation | Average | 6.09 | 1111 | |
D | Deviation | Standard | 8.24 | 1111 | |
E | K-fold cv | K | 10 | 1060 | |
F | Goodness of fit | Q2 | 0.9975 | 1060 | |
G | Deviation | Average (cv) | 6.85 | 1060 | |
H | Deviation | Standard (cv) | 9.19 | 1060 |
Molecule Name | Cp(liq,298) calc. (GA) | Dev. (%) | Cp(liq,298) exp. | Dev. (%) | Cp(liq,298) calc. (Vm) |
---|---|---|---|---|---|
1-Propanol | 155.30 | −5.73 | 146.88 | −8.12 | 158.80 |
2-Propanol | 177.70 | −15.07 | 154.43 | −2.83 | 158.80 |
2-Methyl-1-propanol | 183.40 | −1.30 | 181.05 | −5.05 | 190.20 |
1-Butanol | 185.40 | −4.65 | 177.16 | −7.81 | 191.00 |
Cyclopentanol | 204.20 | −10.14 | 185.40 | −9.76 | 203.50 |
2-Butanol | 207.70 | −5.61 | 196.67 | 3.34 | 190.10 |
Isopentyl alcohol | 213.50 | −1.86 | 209.60 | −5.92 | 222.00 |
1-Pentanol | 215.40 | −3.49 | 208.14 | −7.19 | 223.10 |
2-Methyl-2-propanol | 226.50 | −3.61 | 218.60 | 12.76 | 190.70 |
Cyclohexanol | 230.40 | −7.97 | 213.40 | −9.89 | 234.50 |
3-Methyl-2-butanol | 235.80 | 4.11 | 245.90 | 9.68 | 222.10 |
Cyclohexanemethanol | 236.10 | 0.17 | 236.50 | −12.05 | 265.00 |
3,3-Dimethyl-1-butanol | 237.10 | −0.43 | 236.08 | −7.51 | 253.80 |
3-Pentanol | 237.80 | 0.79 | 239.70 | 6.76 | 223.50 |
2-Ethyl-1-butanol | 243.50 | 1.28 | 246.65 | −2.74 | 253.40 |
2-Methyl-1-pentanol | 243.50 | 1.97 | 248.40 | −2.62 | 254.90 |
1-Hexanol | 245.50 | −1.15 | 242.70 | −5.44 | 255.90 |
Cycloheptanol | 256.50 | −2.51 | 250.22 | −6.03 | 265.30 |
2-Methyl-2-butanol | 256.60 | −3.76 | 247.30 | 10.31 | 221.80 |
trans-2-Methylcyclohexanol | 258.50 | 1.70 | 262.98 | −1.30 | 266.40 |
cis-2-Methylcyclohexanol | 258.50 | 3.89 | 268.95 | 1.51 | 264.90 |
4-Methyl-2-pentanol | 265.90 | 2.36 | 272.34 | 6.66 | 254.20 |
3-Methyl-2-pentanol | 265.90 | 3.62 | 275.89 | 7.93 | 254.00 |
Cyclohexaneethanol | 266.20 | −0.08 | 266.00 | −12.03 | 298.00 |
2-Hexanol | 267.90 | −4.52 | 256.31 | 0.20 | 255.80 |
3-Hexanol | 267.90 | 0.51 | 269.27 | 5.49 | 254.50 |
1-Heptanol | 275.50 | −0.25 | 274.81 | −4.84 | 288.10 |
1-Methylcyclohexanol | 279.20 | −0.05 | 279.05 | 5.03 | 265.00 |
2-Methyl-2-pentanol | 286.70 | 0.81 | 289.03 | 11.84 | 254.80 |
3-Methyl-3-pentanol | 286.70 | 2.25 | 293.30 | 13.57 | 253.50 |
2,4-Dimethyl-3-pentanol | 294.00 | 5.77 | 312.00 | 8.53 | 285.40 |
5-Methyl-2-hexanol | 296.00 | −0.27 | 295.20 | 2.74 | 287.10 |
Cyclohexanepropanol | 296.20 | −1.09 | 293.00 | −12.70 | 330.20 |
2-Heptanol | 297.90 | 0.24 | 298.63 | 3.59 | 287.90 |
3-Heptanol | 297.90 | 5.19 | 314.20 | 8.37 | 287.90 |
4-Heptanol | 297.90 | 2.89 | 306.77 | 6.15 | 287.90 |
2-Ethyl-1-hexanol | 303.60 | 4.38 | 317.50 | −0.28 | 318.40 |
2-Methyl-1-heptanol | 303.60 | 3.00 | 313.00 | −2.01 | 319.30 |
5-Methyl-1-heptanol | 303.60 | 0.20 | 304.20 | −4.73 | 318.60 |
1-Octanol | 305.60 | 2.08 | 312.10 | −2.40 | 319.60 |
2-Methyl-2-hexanol | 316.70 | −1.01 | 313.54 | 8.50 | 286.90 |
2,5-Dimethyl-3-hexanol | 324.00 | 4.54 | 339.40 | 6.25 | 318.20 |
2-Methyl-4-heptanol | 326.00 | 1.75 | 331.80 | 4.01 | 318.50 |
4-Methyl-2-heptanol | 326.00 | −4.32 | 312.50 | −1.70 | 317.80 |
4-Methyl-3-heptanol | 326.00 | −5.43 | 309.20 | −2.81 | 317.90 |
6-Methyl-2-heptanol | 326.00 | −3.46 | 315.10 | −1.30 | 319.20 |
6-Methyl-3-heptanol | 326.00 | −4.99 | 310.50 | −2.77 | 319.10 |
2-Octanol | 328.00 | 0.64 | 330.10 | 3.00 | 320.20 |
3-Octanol | 328.00 | 3.10 | 338.50 | 5.44 | 320.10 |
4-Octanol | 328.00 | 1.23 | 332.09 | 3.64 | 320.00 |
1-Nonanol | 335.70 | 1.55 | 341.00 | −3.37 | 352.50 |
2-Methyl-2-heptanol | 346.80 | −2.73 | 337.60 | 5.45 | 319.20 |
4-Methyl-4-heptanol | 346.80 | 5.48 | 366.90 | 13.25 | 318.30 |
2-Nonanol | 358.00 | −0.47 | 356.32 | 1.10 | 352.40 |
3-Nonanol | 358.00 | 4.18 | 373.63 | 5.71 | 352.30 |
4-Nonanol | 358.00 | 2.68 | 367.86 | 4.26 | 352.20 |
5-Nonanol | 358.00 | 3.44 | 370.75 | 4.98 | 352.30 |
3,7-Dimethyl-1-octanol | 361.80 | 1.47 | 367.21 | −4.05 | 382.10 |
n-Decyl alcohol | 365.70 | 3.00 | 377.00 | −1.83 | 383.90 |
5-Decanol | 388.10 | 4.35 | 405.77 | 5.24 | 384.50 |
1-Undecanol | 395.80 | 2.59 | 406.34 | −2.60 | 416.90 |
1-Dodecanol | 425.80 | 2.88 | 438.42 | −2.44 | 449.10 |
1-Tridecanol | 455.90 | 4.22 | 476.00 | −1.11 | 481.30 |
Myristyl alcohol | 486.00 | 3.91 | 505.80 | −1.52 | 513.50 |
1-Pentadecanol | 516.00 | 3.57 | 535.10 | −1.98 | 545.70 |
1-Hexadecanol | 546.10 | −4.26 | 523.80 | −10.33 | 577.90 |
MAPD | 3.02 | 5.51 |
Molecule Name | Cp(liq,298) calc. (GA) | Dev. (%) | Cp(liq,298) Exp. | Dev. (%) | Cp(liq,298) Calc.(Vm) |
---|---|---|---|---|---|
Cyclopentane | 130.70 | −1.48 | 128.80 | −15.30 | 148.50 |
Pentane | 164.30 | 1.73 | 167.19 | −0.01 | 167.20 |
Cyclohexane | 156.80 | 0.82 | 158.10 | −12.14 | 177.30 |
Hexane | 194.30 | 1.70 | 197.66 | 0.08 | 197.50 |
Cycloheptane | 183.00 | −1.32 | 180.61 | −13.23 | 204.50 |
Heptane | 224.40 | 0.41 | 225.33 | −1.10 | 227.80 |
Cyclooctane | 209.10 | 2.98 | 215.53 | −10.29 | 237.70 |
Octane | 254.40 | 0.50 | 255.68 | −0.99 | 258.20 |
Molecule Name | Cp(liq,298) GA-Calc. | Dev. (%) | Cp(liq,298) Exp. | Dev. (%) | Cp(liq,298) Vm-Calc. |
---|---|---|---|---|---|
1-Ethyl-3-methylimidazolium bromide | 256.40 | 3.17 | 264.80 | 3.29 | 256.10 |
1-Propyl-3-methylimidazolium bromide | 286.50 | −1.81 | 281.40 | −1.92 | 286.80 |
1-Ethyl-3-methylimidazolium thiocyanate | 300.00 | −6.59 | 281.45 | −4.96 | 295.40 |
1-Ethyl-3-methylimidazolium acetate | 321.10 | 0.25 | 321.90 | 7.86 | 296.60 |
1-Ethyl-3-methylimidazolium tetrafluoroborate | 307.60 | 0.16 | 308.10 | 1.95 | 302.10 |
1,3-Dimethylimidazolium methosulfate | 326.20 | 4.34 | 341.00 | 10.50 | 305.20 |
1-Butyl-3-methylimidazolium chloride | 316.50 | 0.16 | 317.00 | 3.63 | 305.50 |
1-Ethyl-3-methylimidazolium dicyanamide | 313.00 | 0.52 | 314.64 | −0.08 | 314.90 |
1-Butyl-3-methylimidazolium bromide | 316.50 | 0.06 | 316.70 | −0.38 | 317.90 |
N-Methyl-2-hydroxyethylammonium propionate | 333.30 | −1.62 | 328.00 | 2.10 | 321.10 |
1-Ethyl-3-methylimidazolium methanesulfonate | 345.40 | 0.03 | 345.50 | 6.80 | 322.00 |
1-Ethyltetrahydrothiophenium dicyanamide | 339.60 | −1.26 | 335.38 | 1.34 | 330.90 |
1-Ethyl-3-methylimidazolium methylsulfate | 353.70 | −3.72 | 341.00 | 0.67 | 338.70 |
1-Ethyl-3-methylimidazolium hexafluorophosphate | 353.00 | −2.74 | 343.60 | 0.67 | 341.30 |
1-Butyl-3-methylimidazolium iodide | 316.50 | −0.80 | 314.00 | −8.82 | 341.70 |
1-Benzyl-3-methylimidazolium chloride | 341.00 | −0.47 | 339.40 | −1.30 | 343.80 |
1-Ethylpyridinium triflate | 348.70 | 0.88 | 351.80 | 0.71 | 349.30 |
1-Ethyl-3-methylimidazolium trifluoromethylsulfonate | 363.80 | −0.28 | 362.80 | 3.64 | 349.60 |
N-Methyl-2-hydroxyethylammonium butanoate | 363.40 | −0.66 | 361.00 | 2.13 | 353.30 |
1-Butyl-3-methylimidazolium thiocyanate | 360.20 | 6.44 | 385.00 | 7.53 | 356.00 |
1-Butyl-3-methylimidazolium acetate | 381.20 | 0.52 | 383.20 | 6.16 | 359.60 |
1-Butyl-3-methylimidazolium tetrafluoroborate | 367.70 | −0.79 | 364.80 | 0.63 | 362.50 |
1-Ethyl-3-methylimidazolium ethosulfate | 383.30 | −1.40 | 378.00 | 2.99 | 366.70 |
1-Propyl-3-methylimidazolium hexafluorophosphate | 383.00 | −2.30 | 374.40 | 0.64 | 372.00 |
1-Butyl-3-methylimidazolium dicyanoamide | 373.10 | −2.22 | 365.00 | −2.19 | 373.00 |
1-Butyl-3-methylimidazolium trifluoroacetate | 411.10 | −0.71 | 408.20 | 5.66 | 385.10 |
N-Methyl-2-hydroxyethylammonium pentanoate | 393.40 | 1.90 | 401.00 | 3.87 | 385.50 |
1-Butyltetrahydrothiophenium dicyanamide | 399.70 | −1.14 | 395.19 | 0.96 | 391.40 |
1-Butyl-3-methylpyridinium tetrafluoroborate | 379.20 | 2.27 | 388.00 | −1.26 | 392.90 |
1-Ethyl-3-methylpyridinium ethylsulfate | 394.70 | −1.47 | 389.00 | −2.08 | 397.10 |
1-Butyl-3-methylimidazolium methosulfate | 413.80 | 0.53 | 416.00 | 4.50 | 397.30 |
1-Benzyl-3-methylimidazolium tetrafluoroborate | 392.20 | −1.21 | 387.50 | −3.23 | 400.00 |
1-Butyl-3-methylimidazolium hexafluorophosphate | 413.10 | −1.32 | 407.70 | 1.37 | 402.10 |
1-Butyl-1-methylpyrrolidinium dicyanamide | 397.80 | 3.68 | 413.00 | 1.86 | 405.30 |
1-Butyl-3-methylimidazolium trifluoromethylsulfonate | 423.90 | −1.65 | 417.00 | 1.75 | 409.70 |
1-Hexyl-3-methylimidazolium tetrafluoroborate | 427.90 | −2.86 | 416.00 | −1.32 | 421.50 |
1-Pentyl-3-methylimidazolium hexafluorophosphate | 443.10 | −1.30 | 437.40 | 1.03 | 432.90 |
1-Butyl-1-methylpyrrolidinium trifluoromethanesulfonate | 448.70 | −3.15 | 435.00 | −0.55 | 437.40 |
1-Ethyl-3-methylimidazolium toluenesulfonate | 486.30 | −0.43 | 484.20 | 6.84 | 451.10 |
1-Hexyl-3-methylimidazolium trifluoromethylsulfonate | 484.00 | 3.64 | 502.30 | 6.43 | 470.00 |
1-Octyl-3-methylimidazolium tetrafluoroborate | 488.00 | 2.01 | 498.00 | 2.99 | 483.10 |
1-Ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 506.70 | −1.34 | 500.00 | 3.36 | 483.20 |
N-Ethylpyridinium bis(trifluoromethylsulfonyl)amide | 491.50 | 2.12 | 502.15 | 2.98 | 487.20 |
1-Ethyl-3-methylimidazolium 2-(2-methoxyethoxy)ethylsulfate | 530.50 | −0.86 | 526.00 | 6.29 | 492.90 |
1-Heptyl-3-methylimidazolium hexafluorophosphate | 503.30 | −0.54 | 500.60 | 1.34 | 493.90 |
1-Isopropyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 535.20 | −1.00 | 529.90 | 3.25 | 512.70 |
1-Propyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 536.70 | −0.34 | 534.90 | 4.08 | 513.10 |
1-Butyl-3-methylimidazolium toluenesulfonate | 546.40 | 0.36 | 548.40 | 6.20 | 514.40 |
N-Ethyl-2-methylpyridinium bis(trifluoromethylsulfonyl)amide | 535.30 | −0.15 | 534.50 | 3.55 | 515.50 |
1-Octyl-3-methylimidazolium hexafluorophosphate | 533.30 | 0.52 | 536.10 | 2.16 | 524.50 |
1-Cyclopropylmethyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 551.50 | −2.30 | 539.10 | 1.21 | 532.60 |
Trimethyl butylammonium bis(trifluoromethylsulfonyl)amide | 561.10 | −0.34 | 559.20 | 4.02 | 536.70 |
1,2-Diethylpyridinium bis(trifluoromethanesulfonyl) amide | 565.40 | 0.12 | 566.10 | 4.82 | 538.80 |
1-Butyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 566.80 | −0.16 | 565.90 | 4.22 | 542.00 |
1-sec-Butyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 565.30 | −1.47 | 557.10 | 2.64 | 542.40 |
1-Methyl-1-propylpyrrolidinium bis(trifluoromethanesulfonyl) amide | 561.50 | −1.35 | 554.00 | 1.93 | 543.30 |
1-Isobutyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 564.80 | −1.38 | 557.10 | 2.48 | 543.30 |
N-Propyl-2-methylpyridinium bis(trifluoromethylsulfonyl)amide | 565.40 | −1.33 | 557.96 | 2.18 | 545.80 |
N-Butylpyridinium bis(trifluoromethanesulfonyl) amide | 551.60 | 2.63 | 566.52 | 3.50 | 546.70 |
1-Nonyl-3-methylimidazolium hexafluorophosphate | 563.40 | 1.05 | 569.40 | 2.79 | 553.50 |
N-Octylisoquinolinium thiocyanate | 528.30 | −1.21 | 522.00 | −6.88 | 557.90 |
1-Butyltetrahydrothiophenium bis(trifluoromethylsulfonyl) amide | 593.40 | 0.44 | 596.00 | 6.12 | 559.50 |
N-Ethyl-4-dimethylaminopyridinium bis(trifluoromethanesulfonyl) amide | 591.20 | 0.52 | 594.30 | 4.37 | 568.30 |
1-Pentyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 596.90 | −0.22 | 595.60 | 4.08 | 571.30 |
1-Ethyl-2-propylpyridinium bis(trifluoromethanesulfonyl) amide | 595.40 | −0.25 | 593.90 | 3.25 | 574.60 |
1-Isobutyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide | 589.60 | −1.27 | 582.20 | 1.03 | 576.20 |
1-Isobutyl-3-methylpyridinium bis(trifluoromethylsulfonyl)amide | 576.30 | 0.47 | 579.00 | 0.40 | 576.70 |
N-Butyl-3-methylpyridinium bis(trifluoromethylsulfonyl)amide | 578.20 | −0.02 | 578.10 | 0.14 | 577.30 |
1-Butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide | 591.50 | −3.41 | 572.00 | −1.05 | 578.00 |
1-Butyl-3-cyanopyridinium bis(trifluoromethylsulfonyl)amide | 590.00 | −0.68 | 586.00 | 1.11 | 579.50 |
1-Benzyl-3-methylimidazolium bis(trifluoromethylsulfonyl) amide | 591.20 | 2.73 | 607.80 | 4.34 | 581.40 |
1-Decyl-3-methylimidazolium hexafluorophosphate | 593.40 | 1.64 | 603.30 | 3.03 | 585.00 |
1-Pentyltetrahydrothiophenium bis(trifluoromethylsulfonyl) amide | 623.50 | 0.56 | 627.00 | 6.19 | 588.20 |
1-Hexyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 626.90 | 0.37 | 629.20 | 4.04 | 603.80 |
1-Butyl-1-methylpiperidinium bis(trifluoromethylsulfonyl)amide | 617.70 | −1.68 | 607.50 | 0.23 | 606.10 |
1-Ethyl-2-butylpyridinium bis(trifluoromethanesulfonyl) amide | 625.50 | −0.30 | 623.60 | 2.79 | 606.20 |
N-Hexylpyridinium bis(trifluoromethanesulfonyl) amide | 611.80 | 0.03 | 612.00 | 0.83 | 606.90 |
1-Methyl-1-pentylpyrrolidinium bis(trifluoromethanesulfonyl) amide | 621.60 | 0.16 | 622.60 | 2.28 | 608.40 |
1-Butyl-3-methylimidazolium octylsulfate | 623.80 | 1.76 | 635.00 | 3.92 | 610.10 |
1-Cyclohexylmethyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 617.50 | −0.06 | 617.10 | 0.26 | 615.50 |
1-Hexyltetrahydrothiophenium bis(trifluoromethylsulfonyl) amide | 653.60 | −1.18 | 646.00 | 4.30 | 618.20 |
N-Butyl-4-dimethylaminopyridinium bis(trifluoromethanesulfonyl) amide | 651.40 | 0.96 | 657.71 | 4.71 | 626.70 |
1-Heptyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 657.00 | 0.33 | 659.20 | 4.31 | 630.80 |
1-Ethyl-2-pentylpyridinium bis(trifluoromethanesulfonyl) amide | 655.60 | −0.44 | 652.70 | 2.47 | 636.60 |
1-Hexyl-3-methylpyridinium bis(trifluoromethylsulfonyl)amide | 638.30 | −2.29 | 624.00 | −2.20 | 637.70 |
1-Hexyl-1-methylpyrrolidinium bis(trifluoromethanesulfonyl) amide | 651.70 | 0.52 | 655.10 | 2.49 | 638.80 |
1-Hexyl-4-cyanopyridinium bis(trifluoromethylsulfonyl)amide | 650.10 | −2.70 | 633.00 | −1.04 | 639.60 |
1-Hexyl-3-cyanopyridinium bis(trifluoromethylsulfonyl)amide | 650.10 | 1.20 | 658.00 | 2.78 | 639.70 |
1-Dodecyl-3-methylimidazolium hexafluorophosphate | 653.60 | 1.91 | 666.30 | 2.97 | 646.50 |
1-Heptyltetrahydrothiophenium bis(trifluoromethylsulfonyl) amide | 683.60 | 0.20 | 685.00 | 5.37 | 648.20 |
1-Octyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 687.10 | 0.45 | 690.20 | 3.80 | 664.00 |
1-Methyl-1-heptylpyrrolidinium bis(trifluoromethanesulfonyl) amide | 681.70 | 0.50 | 685.10 | 2.96 | 664.80 |
1-Octylpyridinium bis(trifluoromethylsulfonyl)amide | 671.90 | 2.06 | 686.00 | 2.93 | 665.90 |
1-Ethyl-2-hexylpyridinium bis(trifluoromethanesulfonyl) amide | 685.60 | −0.01 | 685.50 | 2.68 | 667.10 |
1-Octyltetrahydrothiophenium bis(trifluoromethylsulfonyl) amide | 713.70 | 0.74 | 719.00 | 5.63 | 678.50 |
1-(3,4,5,6-Perfluorohexyl)-3-methylimidazolium-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 719.30 | 0.79 | 725.00 | 6.40 | 678.60 |
4-Dimethylamino-1-hexylpyridinium bis(trifluoromethanesulfonyl) amide | 711.50 | 2.67 | 731.00 | 5.99 | 687.20 |
1-Ethyl-2-heptylpyridinium bis(trifluoromethanesulfonyl) amide | 715.70 | 0.25 | 717.50 | 2.80 | 697.40 |
1-Methyl-1-octylpyrrolidinium bis(trifluoromethanesulfonyl) amide | 711.80 | 0.63 | 716.30 | 2.36 | 699.40 |
1-Octyl-3-cyanopyridinium bis(trifluoromethylsulfonyl)amide | 710.20 | −0.17 | 709.00 | 1.26 | 700.10 |
N-Hexyl-3-methyl-4-dimethylaminopyridinium bis(trifluoromethanesulfonyl) amide | 738.10 | −1.81 | 725.00 | 1.94 | 710.90 |
1-Nonyltetrahydrothiophenium bis(trifluoromethylsulfonyl) amide | 743.70 | −0.36 | 741.00 | 4.01 | 711.30 |
Butyl 1-butylnicotinate bis(trifluoromethylsulfonyl)amide | 728.90 | −3.10 | 707.00 | −0.91 | 713.40 |
1-Decyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 747.20 | 1.01 | 754.80 | 4.03 | 724.40 |
1-Ethyl-2-octylpyridinium bis(trifluoromethanesulfonyl) amide | 745.70 | 0.49 | 749.40 | 3.26 | 725.00 |
1-Methyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 785.90 | −0.58 | 781.40 | 4.20 | 748.60 |
1-Ethyl-2-nonylpyridinium bis(trifluoromethanesulfonyl) amide | 775.80 | 0.35 | 778.50 | 3.48 | 751.40 |
1-Methyl-1-decylpyrrolidinium bis(trifluoromethanesulfonyl) amide | 771.90 | 0.90 | 778.90 | 2.40 | 760.20 |
1-Ethyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 813.40 | 0.61 | 818.40 | 4.55 | 781.20 |
1-Dodecyl-3-methylimidazolium bis(trifluoromethanesulfonyl) amide | 807.30 | 1.57 | 820.20 | 4.04 | 787.10 |
1-Ethyl-2-decylpyridinium bis(trifluoromethanesulfonyl) amide | 805.80 | 0.67 | 811.20 | 2.79 | 788.60 |
1-Propyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 843.50 | −0.49 | 839.40 | 3.71 | 808.30 |
1-Butyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 873.50 | –0.84 | 866.20 | 3.20 | 838.50 |
1-Pentyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 903.60 | 0.15 | 905.00 | 3.55 | 872.90 |
1-Hexyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 933.70 | 1.15 | 944.60 | 4.74 | 899.80 |
1-Heptyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 963.70 | –0.33 | 960.50 | 3.25 | 929.30 |
1-Octyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 993.80 | 0.12 | 995.00 | 3.59 | 959.30 |
1-Nonyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 1023.80 | −0.02 | 1023.60 | 2.83 | 994.60 |
1-Decyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 1053.90 | –0.76 | 1045.90 | 2.31 | 1021.70 |
1-Undecyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 1084.00 | 0.40 | 1088.30 | 3.55 | 1049.70 |
1-Dodecyl-3-menthyloxymethylimidazolium bis(trifluoromethylsulfonyl)imide | 1114.00 | 0.35 | 1117.90 | 2.85 | 1086.00 |
Tetradecyl trihexylphosphonium bis(trifluoromethylsulfonyl)amide | 1312.10 | −1.02 | 1298.80 | −1.35 | 1316.30 |
MAPD | 1.13 | 3.08 |
Entry | Atom Type | Neighbours | Contribution | Occurrences | Molecules |
---|---|---|---|---|---|
1 | B(-) | F4 | 2.99 | 1 | 1 |
2 | C sp3 | H3C | 37.12 | 569 | 246 |
3 | C sp3 | H3N | 101.28 | 50 | 34 |
4 | C sp3 | H3N(+) | 99.59 | 7 | 4 |
5 | C sp3 | H3O | 68.06 | 51 | 35 |
6 | C sp3 | H3S | 45.85 | 3 | 3 |
7 | C sp3 | H3P | 131.12 | 1 | 1 |
8 | C sp3 | H3Si | 59.18 | 14 | 5 |
9 | C sp3 | H2C2 | 25.45 | 1427 | 249 |
10 | C sp3 | H2CN | 82.72 | 89 | 56 |
11 | C sp3 | H2CN(+) | 81.35 | 19 | 15 |
12 | C sp3 | H2CO | 64.67 | 210 | 108 |
13 | C sp3 | H2CS | 72.27 | 22 | 12 |
14 | C sp3 | H2CF | 53.68 | 4 | 1 |
15 | C sp3 | H2CCl | 50.12 | 4 | 1 |
16 | C sp3 | H2CBr | 54.73 | 5 | 2 |
17 | C sp3 | H2CJ | 52.94 | 4 | 1 |
18 | C sp3 | H2CSi | 63.12 | 1 | 1 |
19 | C sp3 | H2N2 | 134.39 | 13 | 3 |
20 | C sp3 | H2O2 | 108.47 | 12 | 3 |
21 | C sp3 | H2S2 | −6.67 | 3 | 3 |
22 | C sp3 | HC3 | 11.92 | 164 | 73 |
23 | C sp3 | HC2N | 72.94 | 28 | 23 |
24 | C sp3 | HC2N(+) | 70.74 | 29 | 28 |
25 | C sp3 | HC2O | 51.84 | 161 | 63 |
26 | C sp3 | HC2S | 47.22 | 4 | 2 |
27 | C sp3 | HC2Si | 142.27 | 1 | 1 |
28 | C sp3 | HCN2 | 137.04 | 1 | 1 |
29 | C sp3 | HCNO | 119.89 | 7 | 5 |
30 | C sp3 | HCNS | 116.08 | 2 | 1 |
31 | C sp3 | HCO2 | 112.62 | 17 | 14 |
32 | C sp3 | HCF2 | 246.8 | 1 | 1 |
33 | C sp3 | HCBr2 | 68.67 | 1 | 1 |
34 | C sp3 | C4 | −2.17 | 81 | 48 |
35 | C sp3 | C3N | 62.09 | 11 | 9 |
36 | C sp3 | C3N(+) | 19.23 | 2 | 2 |
37 | C sp3 | C3O | 27.59 | 10 | 10 |
38 | C sp3 | C3Cl | 78.13 | 1 | 1 |
39 | C sp3 | C3Br | 44.34 | 1 | 1 |
40 | C sp3 | C2NO | 89.86 | 1 | 1 |
41 | C sp3 | C2O2 | 91.75 | 6 | 5 |
42 | C sp3 | C2S2 | 43.86 | 5 | 2 |
43 | C sp3 | CF3 | 69.89 | 2 | 2 |
44 | C sp3 | CSF2 | 0 | 1 | 1 |
45 | C sp3 | CCl3 | 92.28 | 4 | 3 |
46 | C sp2 | H2=C | 39.96 | 6 | 6 |
47 | C sp2 | HC=C | 16.95 | 109 | 65 |
48 | C sp2 | HC=N | 99.99 | 13 | 13 |
49 | C sp2 | HC=O | 43.05 | 14 | 12 |
50 | C sp2 | H=CN | 33.94 | 25 | 17 |
51 | C sp2 | H=CO | 41.99 | 3 | 3 |
52 | C sp2 | H=CS | 36.19 | 7 | 5 |
53 | C sp2 | H=CCl | 19.44 | 1 | 1 |
54 | C sp2 | HN=N | 102.56 | 17 | 14 |
55 | C sp2 | HN=O | 28.91 | 4 | 3 |
56 | C sp2 | H=NO | 112.57 | 1 | 1 |
57 | C sp2 | C2=C | 5.77 | 29 | 22 |
58 | C sp2 | C2=N | 95.44 | 14 | 10 |
59 | C sp2 | C2=N(+) | −9.61 | 2 | 2 |
60 | C sp2 | C=CN | 18.4 | 16 | 15 |
61 | C sp2 | C2=O | 27.68 | 44 | 30 |
62 | C sp2 | C=CO | 25.28 | 15 | 13 |
63 | C sp2 | C=CS | 29.08 | 5 | 4 |
64 | C sp2 | C=CCl | 35.2 | 6 | 3 |
65 | C sp2 | =CN2 | 38.93 | 14 | 14 |
66 | C sp2 | =CN2(+) | 78.32 | 7 | 7 |
67 | C sp2 | CN=N | 87.15 | 19 | 13 |
68 | C sp2 | CN=N(+) | 118.23 | 2 | 1 |
69 | C sp2 | CN=O | 37.33 | 131 | 92 |
70 | C sp2 | =CNO | 55.09 | 1 | 1 |
71 | C sp2 | CN=S | 46.51 | 3 | 3 |
72 | C sp2 | CO=O | 51.25 | 208 | 155 |
73 | C sp2 | CO=O(-) | 15.25 | 41 | 40 |
74 | C sp2 | C=OCl | 61.46 | 2 | 1 |
75 | C sp2 | =CS2 | 45.53 | 12 | 2 |
76 | C sp2 | N2=N | 113.97 | 5 | 3 |
77 | C sp2 | N2=O | 55.72 | 43 | 38 |
78 | C sp2 | N=NO | 91.56 | 1 | 1 |
79 | C sp2 | N2=S | 67.02 | 7 | 7 |
80 | C sp2 | N=NS | 105.95 | 7 | 7 |
81 | C sp2 | NO=O | 63.43 | 8 | 8 |
82 | C sp2 | NO=S | 64.85 | 3 | 3 |
83 | C sp2 | =NOS | 108.01 | 1 | 1 |
84 | C sp2 | NS=S | 62.46 | 4 | 3 |
85 | C sp2 | O2=O | 58.47 | 5 | 5 |
86 | C sp2 | OS=S | 63.23 | 1 | 1 |
87 | C aromatic | H:C2 | 17.96 | 3232 | 437 |
88 | C aromatic | H:C:N | 24.16 | 37 | 20 |
89 | C aromatic | H:C:N(+) | 21.47 | 2 | 1 |
90 | C aromatic | H:N2 | 7.08 | 3 | 3 |
91 | C aromatic | :C3 | 8.04 | 171 | 57 |
92 | C aromatic | C:C2 | 6.56 | 699 | 307 |
93 | C aromatic | C:C:N | 5.85 | 13 | 9 |
94 | C aromatic | :C2N | 24.29 | 172 | 107 |
95 | C aromatic | :C2N(+) | 49.48 | 57 | 42 |
96 | C aromatic | :C2:N | 19.63 | 13 | 7 |
97 | C aromatic | :C2O | 29.21 | 184 | 113 |
98 | C aromatic | :C2P | 15.1 | 6 | 2 |
99 | C aromatic | :C2S | 27.43 | 43 | 28 |
100 | C aromatic | :C2Si | 58.51 | 53 | 12 |
101 | C aromatic | :C2F | 31.08 | 25 | 9 |
102 | C aromatic | :C2Cl | 34.35 | 57 | 25 |
103 | C aromatic | :C2Br | 37.48 | 18 | 9 |
104 | C aromatic | :C2J | 48.49 | 5 | 3 |
105 | C aromatic | C:N2 | 18.81 | 3 | 1 |
106 | C aromatic | :CN:N | 39.03 | 7 | 5 |
107 | C aromatic | :C:NO | 53.92 | 1 | 1 |
108 | C aromatic | :C:NCl | 49.04 | 3 | 3 |
109 | C aromatic | N:N2 | 36.22 | 4 | 2 |
110 | C aromatic | :N2O | 40.81 | 3 | 1 |
111 | C(+) aromatic | H:N2 | −39.63 | 3 | 3 |
112 | C(+) aromatic | :N3 | −20.94 | 2 | 2 |
113 | C sp | H#C | 103.03 | 2 | 1 |
114 | C sp | C#C | 14.95 | 8 | 3 |
115 | C sp | C#N | 39.64 | 28 | 20 |
116 | C sp | C#N(+) | 62.56 | 1 | 1 |
117 | C sp | #CSi | 0 | 2 | 1 |
118 | C sp | #NO | 58.07 | 2 | 1 |
119 | C sp | =N=O | 110.98 | 6 | 3 |
120 | N sp3 | H2C | −18.62 | 5 | 5 |
121 | N sp3 | H2C(pi) | 15.49 | 129 | 98 |
122 | N sp3 | H2N | 9.51 | 4 | 3 |
123 | N sp3 | H2S | 45.92 | 9 | 9 |
124 | N sp3 | HC2 | −104.07 | 6 | 3 |
125 | N sp3 | HC2(pi) | −56.77 | 78 | 57 |
126 | N sp3 | HC2(2pi) | −9.78 | 82 | 61 |
127 | N sp3 | HCN(pi) | 21.22 | 7 | 5 |
128 | N sp3 | HCN(2pi) | 36.09 | 7 | 7 |
129 | N sp3 | C3 | −159.23 | 15 | 10 |
130 | N sp3 | C3(pi) | −123.38 | 10 | 9 |
131 | N sp3 | C3(2pi) | −83.83 | 27 | 21 |
132 | N sp3 | C3(3pi) | −43.15 | 12 | 6 |
133 | N sp3 | C2N(pi) | −75.07 | 3 | 3 |
134 | N sp3 | C2N(+)(pi) | −52.69 | 7 | 2 |
135 | N sp3 | C2N(2pi) | 25.39 | 3 | 3 |
136 | N sp3 | C2N(+)(2pi) | −41.18 | 2 | 2 |
137 | N sp2 | C=C | −74.59 | 54 | 44 |
138 | N sp2 | C=N | 2.46 | 5 | 3 |
139 | N sp2 | =CN | −98.01 | 7 | 7 |
140 | N sp2 | =CN(+) | −14.76 | 1 | 1 |
141 | N sp2 | =CO | −44.63 | 24 | 11 |
142 | N sp2 | N=N | 17.43 | 3 | 2 |
143 | N aromatic | H2:C(+) | 4.65 | 4 | 2 |
144 | N aromatic | HC:C(+) | 40.44 | 1 | 1 |
145 | N aromatic | C2:C(+) | −3.11 | 7 | 4 |
146 | N aromatic | :C2 | −0.16 | 50 | 33 |
147 | N(+) sp3 | H3C | −6.7 | 35 | 34 |
148 | N(+) sp3 | H2C2 | −73.79 | 4 | 4 |
149 | N(+) sp3 | HC3 | −156.71 | 1 | 1 |
150 | N(+) sp3 | C4 | −233.93 | 2 | 2 |
151 | N(+) sp2 | CO=O(-) | 9.71 | 72 | 49 |
152 | N(+) sp2 | =CO2(-) | −7.42 | 2 | 2 |
153 | N(+) sp2 | NO=O(-) | −2.08 | 10 | 5 |
154 | N(+) aromatic | C:C2 | 0 | 1 | 1 |
155 | N(+) sp | C#C(-) | 25.34 | 3 | 3 |
156 | N(+) sp | #CO(-) | 0 | 1 | 1 |
157 | O(prim) | HC | −23.36 | 106 | 60 |
158 | O(sec) | HC | −16.25 | 117 | 50 |
159 | O(tert) | HC | −3.34 | 6 | 6 |
160 | O | HC(pi) | 4.78 | 218 | 157 |
161 | O | HN(pi) | 16.33 | 3 | 3 |
162 | O | HSi | 16.93 | 8 | 2 |
163 | O | C2 | −70.39 | 60 | 29 |
164 | O | C2(pi) | −39.71 | 125 | 88 |
165 | O | C2(2pi) | −23.91 | 47 | 41 |
166 | O | CN(2pi) | −28.51 | 5 | 5 |
167 | O | CSi | −30.4 | 36 | 9 |
168 | O | N2(2pi) | 1.1 | 7 | 4 |
169 | O | N2(+)(2pi) | −2.2 | 2 | 2 |
170 | O | Si2 | −7.14 | 39 | 8 |
171 | P3 | C3 | −2.25 | 1 | 1 |
172 | P4 | C3=O | 2.25 | 1 | 1 |
173 | P4 | C=OCl2 | 0 | 1 | 1 |
174 | S2 | HC | 10.73 | 1 | 1 |
175 | S2 | HC(pi) | 16.07 | 5 | 5 |
176 | S2 | C2 | −15.43 | 12 | 8 |
177 | S2 | C2(pi) | −30.85 | 14 | 6 |
178 | S2 | C2(2pi) | −10.04 | 24 | 17 |
179 | S2 | CS | −20.66 | 4 | 2 |
180 | S2 | CS(pi) | 6.91 | 6 | 3 |
181 | S4 | C2=O | 5.33 | 2 | 2 |
182 | S4 | C2=O2 | 15.56 | 5 | 5 |
183 | S4 | CN=O2 | 2.75 | 9 | 9 |
184 | S4 | CO=O2(-) | −118.41 | 1 | 1 |
185 | Si | C4 | −197.51 | 3 | 3 |
186 | Si | C3O | −100.79 | 4 | 2 |
187 | Si | C3Cl | −107.38 | 1 | 1 |
188 | Si | C2O2 | −38.26 | 11 | 3 |
189 | Si | CO3 | 10.05 | 20 | 3 |
190 | Si | CCl3 | 57.89 | 2 | 2 |
191 | Si | O4 | 0 | 9 | 9 |
192 | (COH)n | n>1 | 3.46 | 145 | 59 |
193 | H | H Acceptor | 1.19 | 61 | 43 |
194 | Endocyclic bonds | No of single bds | −1.44 | 998 | 149 |
195 | Angle60 | 0.97 | 15 | 2 | |
196 | Angle90 | 0.31 | 12 | 6 | |
197 | Angle102 | 2.16 | 284 | 83 | |
A | Based on | Valid groups | 126 | 802 | |
B | Goodness of fit | r2 | 0.9915 | 734 | |
C | Deviation | Average | 9.36 | 734 | |
D | Deviation | Standard | 12.21 | 734 | |
E | K-fold cv | K | 10 | 663 | |
F | Goodness of fit | q2 | 0.9874 | 663 | |
G | Deviation | Average (cv) | 11.1 | 663 | |
H | Deviation | Standard (cv) | 14.23 | 663 |
Molecule Name | Cp(sol,298) GA-calc | Dev. (%) | Cp(sol,298) exp. | Dev. (%) | Cp(sol,298) Vm−calc. [1] |
---|---|---|---|---|---|
2-Methyl-2-propanol | 135.90 | 6.99 | 146.11 | 18.28 | 119.40 |
2,2-Dimethyl-1,3-propanediol | 158.00 | 13.75 | 183.18 | 13.42 | 158.60 |
Erythritol | 164.20 | −1.42 | 161.90 | 0.99 | 160.30 |
cis-1,2-Cyclohexanediol | 168.00 | −4.74 | 160.40 | −4.68 | 167.90 |
trans-1,2-Cyclohexanediol | 168.00 | −2.94 | 163.20 | −3.00 | 168.10 |
Pentaerythritol | 174.40 | 7.43 | 188.40 | 3.24 | 182.30 |
Hexamethyleneglycol | 187.90 | 1.11 | 190.00 | 2.47 | 185.30 |
Xylitol | 206.90 | 0.05 | 207.00 | 10.14 | 186.00 |
Ethriol | 191.10 | 10.62 | 213.80 | 7.86 | 197.00 |
Inositol | 223.60 | −2.57 | 218.00 | 0.50 | 216.90 |
2-Adamantanol | 193.30 | 6.71 | 207.20 | −6.13 | 219.90 |
1-Adamantanol | 195.60 | 0.56 | 196.70 | −12.10 | 220.50 |
Dulcose | 246.00 | −3.14 | 238.50 | 3.31 | 230.60 |
Isoborneol | 243.10 | 6.88 | 261.06 | 10.21 | 234.40 |
Borneol | 243.10 | 6.88 | 261.06 | 9.68 | 235.80 |
1,8-Octanediol | 238.90 | −1.07 | 236.36 | −0.23 | 236.90 |
Sorbitol | 242.30 | −1.38 | 239.00 | 0.50 | 237.80 |
Menthol | 250.70 | −0.24 | 250.10 | −0.72 | 251.90 |
1,9-Nonanediol | 264.30 | −2.94 | 256.74 | −2.36 | 262.80 |
1,10-Decanediol | 289.80 | −3.77 | 279.26 | −3.34 | 288.60 |
1,11-Undecanediol | 315.20 | −5.85 | 297.79 | −5.58 | 314.40 |
Tri-t-butylmethanol | 351.80 | −0.34 | 350.60 | 6.36 | 328.30 |
1,12-Dodecanediol | 340.70 | −3.17 | 330.23 | −3.05 | 340.30 |
1-Tridecanol | 358.60 | 5.13 | 378.00 | 8.41 | 346.20 |
1,13-Tridecanediol | 366.20 | 0.19 | 366.88 | 0.21 | 366.10 |
Myristyl alcohol | 384.00 | 1.03 | 388.00 | 4.28 | 371.40 |
1,14-Tetradecanediol | 391.60 | −3.16 | 379.61 | −3.24 | 391.90 |
1-Pentadecanol | 409.50 | −2.38 | 400.00 | 0.88 | 396.50 |
1,15-Pentadecanediol | 417.10 | −10.50 | 377.45 | −10.66 | 417.70 |
1-Hexadecanol | 435.00 | −3.08 | 422.00 | 0.09 | 421.60 |
1,16-Hexadecanediol | 442.50 | −3.83 | 426.18 | −4.06 | 443.50 |
MAPD | 4.00 | 5.16 |
Molecule Name | Cp(sol,298) GA-Calc. | Dev. (%) | Cp(sol,298) exp. | Dev. (%) | Cp(sol,298) Vm-Calc. [1] |
---|---|---|---|---|---|
Nortricyclene | 130.70 | −1.32 | 129.00 | −9.15 | 140.80 |
Norbornane | 163.80 | −8.48 | 151.00 | 0.93 | 149.60 |
Bicyclo[2.2.2]octane | 163.80 | −3.87 | 157.69 | −8.44 | 171.00 |
Adamantane | 183.30 | 3.53 | 190.00 | −5.95 | 201.30 |
Bicyclo[3.3.3]undecane | 236.10 | −10.74 | 213.20 | −9.19 | 232.80 |
Diamantane | 222.10 | 0.58 | 223.40 | −17.32 | 262.10 |
Perhydrophenanthrene | 279.60 | 3.42 | 289.50 | −0.73 | 291.60 |
Tri-t-butylmethane | 339.50 | 4.31 | 354.80 | 15.30 | 300.50 |
Cetane | 431.00 | 2.44 | 441.80 | 13.26 | 383.20 |
Octadecane | 481.90 | 0.77 | 485.64 | 11.70 | 428.80 |
Docosane | 583.80 | −3.58 | 563.60 | 7.59 | 520.80 |
2,11-Dicyclohexyldodecane | 563.40 | −1.09 | 557.30 | 4.65 | 531.40 |
1,1-Dicyclohexyldodecane | 565.20 | −0.46 | 562.60 | 5.44 | 532.00 |
Hexacosane | 685.60 | −3.69 | 661.20 | 7.43 | 612.10 |
Triacontane | 787.40 | 2.65 | 808.80 | 13.03 | 703.40 |
Dotriacontane | 838.40 | −4.02 | 806.00 | 7.07 | 749.00 |
Tetratriacontane | 889.30 | −0.21 | 887.40 | 10.45 | 794.70 |
Pentatriacontane | 914.70 | 0.13 | 915.90 | 10.74 | 817.50 |
MAPD | 3.07 | 8.80 |
Molecule name | Cp(sol,298) GA-calc. | Cp(sol,298) Exp. | Cp(sol,298) Vm-Calc. [1] | ||
---|---|---|---|---|---|
Non-Ionic | Zwitter-Ionic | Zwitter-Ionic | Non-Ionic | ||
Glycine | 120.20 | 89.90 | 99.30 | 95.90 | 91.30 |
Alanine | 147.60 | 116.50 | 119.90 | 118.50 | 116.10 |
N-Methylglycine | 136.00 | 122.40 | 118.20 | 119.10 | 116.90 |
Serine | 152.70 | 121.70 | 135.60 | 126.20 | 126.50 |
Aminobutyric acid | 173.00 | 142.00 | 146.40 | 140.90 | 140.70 |
Proline | 162.20 | 137.30 | 150.40 | 149.80 | 150.90 |
Threonine | 183.00 | 152.00 | 155.31 | 153.30 | 154.70 |
Aspartic acid | 193.00 | 162.00 | 155.18 | 155.10 | 156.00 |
Asparagine | 189.80 | 158.70 | 159.80 | 157.60 | 159.30 |
Valine | 196.70 | 165.60 | 165.00 | 162.90 | 165.40 |
5-Aminopentanoic acid | 196.60 | 166.30 | 163.70 | 164.30 | 166.60 |
Ornithine | 225.40 | 194.40 | 191.20 | 179.20 | 183.60 |
Glutamine | 214.00 | 183.00 | 184.18 | 182.30 | 186.50 |
Leucine | 222.10 | 191.10 | 200.80 | 183.90 | 188.20 |
Isoleucine | 222.10 | 191.10 | 188.28 | 184.70 | 189.90 |
Methionine | 238.50 | 207.40 | 205.16 | 189.10 | 194.30 |
N-Phenylglycine | 196.10 | 162.20 | 177.40 | 194.60 | 198.60 |
Phenylalanine | 232.20 | 201.10 | 203.10 | 215.50 | 221.60 |
8-Aminooctanoic acid | 273.00 | 242.70 | 251.70 | 232.80 | 241.90 |
Tyrosine | 248.20 | 217.10 | 216.44 | 236.20 | 238.10 |
Tryptophane | 268.30 | 237.20 | 238.15 | 252.00 | 263.90 |
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Naef, R. Calculation of the Isobaric Heat Capacities of the Liquid and Solid Phase of Organic Compounds at 298.15K by Means of the Group-Additivity Method. Molecules 2020, 25, 1147. https://doi.org/10.3390/molecules25051147
Naef R. Calculation of the Isobaric Heat Capacities of the Liquid and Solid Phase of Organic Compounds at 298.15K by Means of the Group-Additivity Method. Molecules. 2020; 25(5):1147. https://doi.org/10.3390/molecules25051147
Chicago/Turabian StyleNaef, Rudolf. 2020. "Calculation of the Isobaric Heat Capacities of the Liquid and Solid Phase of Organic Compounds at 298.15K by Means of the Group-Additivity Method" Molecules 25, no. 5: 1147. https://doi.org/10.3390/molecules25051147