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Article

Prediction of Standard Enthalpy of Formation by a QSPR Model

Department of Chemical Engineering, Faculty of Engineering, University of Tehran, P.O.Box: 11365-4563, Tehran, Iran
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2007, 8(5), 407-432; https://doi.org/10.3390/i8050407
Submission received: 1 March 2007 / Accepted: 27 March 2007 / Published: 22 May 2007
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)

Abstract

:
The standard enthalpy of formation of 1115 compounds from all chemical groups, were predicted using genetic algorithm-based multivariate linear regression (GA-MLR). The obtained multivariate linear five descriptors model by GA-MLR has correlation coefficient (R2 = 0.9830). All molecular descriptors which have entered in this model are calculated from chemical structure of any molecule. As a result, application of this model for any compound is easy and accurate.

1. Introduction

Physical and thermodynamic properties data of compounds are needed in the design and operation of industrial chemical processes. Of them, standard enthalpy of formation or standard heat of formation, ΔHf° is an important fundamental physical property of compounds which is defined as change of enthalpy that accompanies the formation of 1 mole of compound in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atm of pressure and the specified temperature usually 298 K or 25 degrees Celsius). All elements in their standard states (such as hydrogen gas, solid carbon in the form of graphite, etc.) have standard enthalpy of formation of zero, as there is no change involved in their formation.
The standard enthalpy change of formation is used in thermo-chemistry to find the standard enthalpy change of reaction. This is done by subtracting the summation of the standard enthalpies of formation of the reactants from the summation of the standard enthalpies of formation of the products, as shown in the equation below.
Δ H r e a c t i o n = p Δ H f - r Δ H f
where ΔHreaction, p Δ H f, and r Δ H f are standard enthalpy change of reaction, standard enthalpies of formation of the products, and standard enthalpies of formation of the reactants, respectively.
There are many methods for calculation of ΔHf° in the literature, but of them, only three methods are widely used. These three methods are the Benson method [1], Jobak and Reid method [2], and Constantinou and Gani method [3]. All of these methods are classified in the field of group contribution methods which in these methods, the property of a compound is estimated as a summation of the contributions of simple chemical groups which can occur in the molecular structure. They provide the important advantage of rapid estimates without requiring substantial computational resources.
Application of quantitative structure-property relationship (QSPR) models in prediction and estimation of physical properties of materials is widely developing [45]. In QSPR, advanced mathematical methods (Genetic algorithm, neural networks, and etc.) are used to find a relation between property of interest and the basic molecular properties which are obtained solely from the chemical structure of compounds and called “molecular descriptors”.
In this study, a new QSPR model for prediction of ΔHf° of 1115 organic compounds is presented. These 1115 compounds belong to all families of materials, as a result the obtained model can be applied for prediction of ΔHf° for any compound.

2. Procedures and Methods

2.1. Data set

Many compilations for ΔHf° have been published in the literature, but of them, we selected the DIPPR 801 [6] compilation for our problem. This compilation has been recommended by AIChE (American Institute of Chemical Engineers). From this compilation, 1115 compounds were selected and ΔHf° of them were extracted from this database.

2.2. Calculation of Molecular Descriptors

In the calculation of molecular descriptors, the optimized chemical structures of compounds are needed. The chemical structures of all 1115 compounds in our data set, were drawn in Hyperchem software [7], and pre-optimized using MM+ mechanical fore field. A more precise optimization was done with PM3 semi empirical method in Hyperchem.
In the next step for all 1115 compounds, molecular descriptors were calculated by Dragon software [8]. Dragon can calculate 1664 molecular descriptors for any chemical structure. After calculating molecular descriptors for all 1115 chemical structures, we must reject non informative descriptors from output of Dragon. First the descriptors with standard deviation lower than 0.0001, have been rejected because these descriptors were near constant. In second step, the descriptors with only one value different from the remaining ones are rejected. In the third step, the pair correlation of each two descriptors was checked and one of two descriptors with a correlation coefficient equal one (as a threshold value) was excluded. For each pair of correlated descriptors, the one showing the highest pair correlation with the other descriptors rejected from the pool of descriptors.
Finally, the pool of molecular descriptors was reduced by deleting descriptors which could not be calculated for every structure in our data set.
As a result, from the calculated 1664 molecular descriptors, in the first step, only 1477 molecular descriptors remained in the pool of molecular descriptors.

2.3. Methods of calculation and results

In this step, 20% of our database (223 compounds) is randomly removed and entered to test set as an excluded data set. This test set was used in next steps, only for testing the prediction power of obtained model and are not used for developing model. The remaining 80% (892 compounds) of our data set was used for training set.
In this step our problem is to find the best multivariate linear model which has the most accuracy as well as the minimum number of possible molecular descriptors. One of the best algorithms for these types of problems has been proposed by Leardi et al. [9]. In order to perform this algorithm, a program was written based on MATLAB (Mathworks Inc. software). This program finds the best multivariate linear model by genetic algorithm based multivariate linear regression (GA-MLR) which has proposed by Leardi et al. [9] and we have used it to our previous works, successfully [1012]. The input of this program is the molecular descriptors which have been obtained in previous section and the desired number of parameter of multivariate linear model. The fitness function of our program was the cross validated coefficient. For obtaining the best model, we must consider the effect of increase in the number of molecular descriptors on the increase in the value of the cross validated coefficient. When the cross validated coefficient was quite constant with increasing the number of molecular descriptors, we must stop our search, and the best result has been obtained.
For obtaining the best multivariate linear model, first, we started with one molecular descriptor model and found the best multivariate linear model, then the two molecular descriptors model were tested, and the best multivariate linear two descriptors model was found. This work was repeated and the number of descriptors was increased, till, we found that increase in the number of molecular descriptors does not affect the accuracy of the best model. The best obtained model has six parameters and is presented below:
Δ H f = 50.1688 - 80.52012 n S K + 5364546 S C B O - 169.21889 S C B O - 174.75477 n F - 266.57659 n H M
where the molecular descriptors of Eq.(2) and their meaning are presented in Table 1.
The statistical parameters of fitting for Eq.(1) are the following: R2 = 0.9830, F = 10239.02, s = 58.541, Q2 = 0.9826, where R2 is the squared correlation coefficient, F is the Fisher factor, s is the standard deviation, and Q2 is the squared cross validated correlation coefficient. The statistical parameters of coefficients of the Eq. (2) are presented in the Table 2.

2.4. Validation of Model

There are many validation techniques for checking the validation of the obtained model [13].
Todeschini et al. [13] presented a quick rule for checking the validity of obtained model. This rule compares the multivariate correlation index KX of X-block of the predictor variables with the multivariate correlation index KXY obtained by the augmented X-block matrix by adding the column of the response variable. This rule says that if KXY is greater than KX, the model is predictive [13]. Obtained values of these two indexes in our problem are = 31.62 KX and = 40.81 KXY, as a result, with respect to this quick rule, obtained model is predictive (KXY > KX).
Cross-validation technique is the most common validation technique [13]. In this technique each member of our data set is deleted, then, with the other members a model is produced, and the value of the deleted object is predicted. This technique is performed for all members of the data set and finally, a squared cross validated correlation is obtained. In our problem this work was done and the values of squared cross validated correlation (Q2) was 0.9826. The difference between R2 and Q2 is promising and thus validity of this model is confirmed by this technique.
Another validation technique is bootstrap technique [13]. By this technique, validation is performed by randomly generating training sets with sample repetitions and then evaluating the predicted responses of the samples not included in the training set. This work usually repeated thousands of times. After 5000 times repetition of this technique, the parameter QBoot2 was 0.9823. As can be found, the difference between the QBoot2, Q2, and R2 is promising and thus the predictive power of model is confirmed.
Ultimately, the last validation technique which we used was external validation. In this section by means of test set which we had separated from the original data set, the prediction power of the Eq.(2) was checked. The squared cross validated coefficient for the test (Qext2 ) set is 0.9894, which the promising difference between this value and the value of Q2 shows the prediction power of the Eq. (2).
The calculated and DIPPR 801 values of ΔHf° for training set are presented in the Table-3. Also, the predicted and DIPPR 801 values of ΔHf° for test set are presented in Table 4. The comparison between the results of Eq.(2) and the DIPPR 801 values for training set and test set are shown in the Figure 1.

3. Discussion

In the formation of a molecule from its constituent elements, ΔHf°, is the difference between the enthalpy of this molecule and the elements which conform it. This enthalpy is a result of breaking bonds of the elements in the free form (breaking reaction) and formation of new bonds in the molecule of product (formation reaction). Breaking reaction is endothermic, but the formation reaction is exothermic.
Any thing which can affect the bond properties and strength of the bonds in the molecule can affect the value of ΔHf° of that molecule. Of them, the number of atoms and number of the bonds and order of the bonds and number of non-organic elements (heavy atoms) in a molecule directly affect on the value of ΔHf°.
Increase in the values of number of atoms in the H-depleted chemical structure of molecule decreases ΔHf° of a molecule. Increase in the order of bonds in a molecule increases ΔHf°. Also the number of atoms which are commonly existed in all molecules such as oxygen and fluorine atoms, and even heavy atoms affect ΔHf° of a molecule. Increase in the number of these atoms in a molecule, decreases ΔHf° of that molecule.

4. Conclusions

In this present study, a simple five descriptors linear model was presented. This model was the result of a QSPR study on the standard enthalpy of formation of 1115 compounds. These compounds have been selected from all families of compounds as a result there are no specific limit in application of this model. Also the simplicity of the use of it is one of the advantages of this model.
All molecular descriptors of this model can be easily calculated from the chemical structure of a molecule.
Figure 1. Comparison between the results of Eq. (2) for training set and predicted values for training set.
Figure 1. Comparison between the results of Eq. (2) for training set and predicted values for training set.
Ijms 08 00407f1
Table 1. The molecular descriptors of Eq. (2) and their meaning.
Table 1. The molecular descriptors of Eq. (2) and their meaning.
VariableMolecular descriptor meaning
nSKNumber of non-H atoms
SCBOSum of conventional bond orders (H-depleted)
nONumber of Oxygen atoms
nFNumber of Fluorine atoms
nHMNumber of Heavy atoms
Table 2. The values of the constants of Eq. (2) and their statistical interpretations.
Table 2. The values of the constants of Eq. (2) and their statistical interpretations.
IDVariableRegression CoefficientErrors Regression CoefficientConfidence Intervals (0.95)Standard Regression Coefficient
0intercept50.160882674.07569600
1nSK−80.520124891.175295−1.0813259193.60196
2SCBO53.645456270.98372230.8586966673.593514
3nO−169.21888951.424115−0.5528559741.061814
4nF−174.75477181.178939−0.6806697491.047946
5nHM−266.57658856.857063−0.1713898921.006101
Table 3. The obtained results from Eq. (2) for training set.
Table 3. The obtained results from Eq. (2) for training set.
IDNameΔHf° (kJ/mol)Res

DIPPR 801Calculated from Eq. (2)
1n-BUTANE−125.79−110.9814.81
2n-HEXANE−198.66−164.7333.93
33-METHYLPENTANE−202.38−164.7337.65
4n-HEPTANE−224.05−191.6132.44
53-METHYLHEXANE−226.44−191.6134.83
63-ETHYLPENTANE−224.56−191.6132.95
72,2-DIMETHYLPENTANE−238.28−191.6146.67
82,3-DIMETHYLPENTANE−233.09−191.6141.48
92,4-DIMETHYLPENTANE−234.6−191.6142.99
103,3-DIMETHYLPENTANE−234.18−191.6142.57
112,2,3-TRIMETHYLBUTANE−236.52−191.6144.91
122-METHYLHEPTANE−255.01−218.4836.53
134-METHYLHEPTANE−251.63−218.4833.15
143-ETHYLHEXANE−250.41−218.4831.93
152,2-DIMETHYLHEXANE−261.88−218.4843.4
162,3-DIMETHYLHEXANE−252.59−218.4834.11
172,4-DIMETHYLHEXANE−257.02−218.4838.54
183,3-DIMETHYLHEXANE−257.53−218.4839.05
192-METHYL-3-ETHYLPENTANE−249.58−218.4831.1
202,2,3-TRIMETHYLPENTANE−256.9−218.4838.42
212,2,4-TRIMETHYLPENTANE−259.16−218.4840.68
222,3,3-TRIMETHYLPENTANE−253.51−218.4835.03
232,3,4-TRIMETHYLPENTANE−255.01−218.4836.53
24n-NONANE−274.68−245.3629.32
253,3,5-TRIMETHYLHEPTANE−304.76−272.2332.53
262,4,4-TRIMETHYLHEXANE−280.2−245.3634.84
273,3-DIETHYLPENTANE−275.39−245.3630.03
282,2,3,3-TETRAMETHYLPENTANE−278.28−245.3632.92
292,2,4,4-TETRAMETHYLPENTANE−279.99−245.3634.63
30SQUALANE−806.3−809.72−3.42
31n-DECANE−300.62−272.2328.39
322,2,5,5-TETRAMETHYLHEXANE−323.51−272.2351.28
33n-UNDECANE−326.6−299.1127.49
34n-DODECANE−352.13−325.9826.15
35n-TRIDECANE−377.69−352.8624.83
36n-TETRADECANE−403.25−379.7323.52
37n-PENTADECANE−428.82−406.622.22
38n-HEXADECANE−456.14−433.4822.66
39n-OCTADECANE−567.14−487.2379.91
40n-NONADECANE−596.21−514.182.11
41n-HENEICOSANE−653.45−567.8585.6
42n-DOCOSANE−682.07−594.7387.34
43n-TRICOSANE−710.69−621.689.09
44n-PENTACOSANE−767.93−675.3592.58
45n-HEXACOSANE−796.55−702.2394.32
46n-HEPTACOSANE−825.17−729.196.07
47n-OCTACOSANE−853.79−755.9897.81
48n-NONACOSANE−882.41−782.8599.56
492-METHYLNONANE−311.9−272.2339.67
505-METHYLNONANE−310−272.2337.77
512,2,4,4,6,8,8-HEPTAMETHYLNONANE−476.87−433.4843.39
523-METHYLOCTANE−278.53−245.3633.17
534-METHYLOCTANE−279.6−245.3634.24
543-ETHYLHEPTANE−275.48−245.3630.12
552,2-DIMETHYLHEPTANE−288.2−245.3642.84
563-METHYLUNDECANE−355.2−325.9829.22
57ETHYLCYCLOPENTANE−163.43−137.9625.47
58cis-1,2-DIMETHYLCYCLOPENTANE−165.27−137.9627.31
59trans-1,3-DIMETHYLCYCLOPENTANE−168.07−137.9630.11
60n-PROPYLCYCLOPENTANE−189.07−164.8424.23
611-METHYL-1-ETHYLCYCLOPENTANE−193.8−164.8428.96
62n-PROPYLCYCLOHEXANE−237.4−191.7145.69
63ISOPROPYLCYCLOHEXANE−239.45−191.7147.74
641,1-DIETHYLCYCLOHEXANE−277.11−218.5958.52
65n-DECYLCYCLOHEXANE−417−379.8337.17
66CYCLOHEPTANE−156.61−137.9618.65
67CYCLOOCTANE−167.74−164.842.9
68trans-1,4-DIETHYLCYCLOHEXANE−266.1−218.5947.51
692,6-DIMETHYLHEPTANE−286.12−245.3640.76
702,2-DIMETHYL-3-ETHYLPENTANE−272.7−245.3627.34
712,4-DIMETHYL-3-ETHYLPENTANE−269.7−245.3624.34
721-TRIACONTENE−761.6−756.085.52
732-METHYL-1-BUTENE−60.96−84.21−23.25
74cis-2-HEXENE−80.11−111.09−30.98
75trans-2-HEXENE−85.52−111.09−25.57
76cis-3-HEXENE−78.95−111.09−32.14
772-METHYL-1-PENTENE−89.96−111.09−21.13
783-METHYL-1-PENTENE−78.16−111.09−32.93
794-METHYL-1-PENTENE−80.04−111.09−31.05
802-METHYL-2-PENTENE−98.53−111.09−12.56
814-METHYL-1-HEXENE−101.5−137.96−36.46
824-METHYL-cis-2-PENTENE−87.03−111.09−24.06
834-METHYL-trans-2-PENTENE−91.55−111.09−19.54
842-ETHYL-1-BUTENE−87.11−111.09−23.98
852,3-DIMETHYL-1-BUTENE−95.6−111.09−15.49
863,3-DIMETHYL-1-BUTENE−88.28−111.09−22.81
872-ETHYL-1-PENTENE−109.9−137.96−28.06
881-HEPTENE−98.37−137.96−39.59
89cis-2-HEPTENE−105.1−137.96−32.86
90trans-2-HEPTENE−109.5−137.96−28.46
91trans-3-HEPTENE−109.33−137.96−28.63
922-METHYL-1-HEXENE−112.6−137.96−25.36
933-ETHYL-1-PENTENE−98.49−137.96−39.47
943-METHYL-1-HEXENE−101.1−137.96−36.86
953-ETHYL-1-HEXENE−124.6−164.84−40.24
962,3,3-TRIMETHYL-1-BUTENE−117.7−137.96−20.26
97cis-3-HEPTENE−104.35−137.96−33.61
981-OCTENE−122−164.84−42.84
992,4,4-TRIMETHYL-1-PENTENE−146.15−164.84−18.69
1002-ETHYL-1-HEXENE−136.42−164.84−28.42
1011-NONENE−148.8−191.71−42.91
1021-UNDECENE−200.8−245.46−44.66
1031-DODECENE−226.2−272.34−46.14
1041-TRIDECENE−253.5−299.21−45.71
1051-TETRADECENE−280.3−326.08−45.78
1061-HEXADECENE−329.24−379.83−50.59
1071-OCTADECENE−374.77−433.58−58.81
1086-METHYL-1-HEPTENE−129.5−164.84−35.34
109CYCLOHEXENE−38.2−57.44−19.24
110trans-2-EICOSENE−446.6−487.33−40.73
111trans-2-PENTADECENE−319.5−352.96−33.46
112cis-2-OCTENE−129.4−164.84−35.44
113trans-3-OCTENE−134.38−164.84−30.46
114cis-4-OCTENE−128.49−164.84−36.35
115trans-4-OCTENE−134.61−164.84−30.23
116cis-3-OCTENE−129.14−164.84−35.7
1171-EICOSENE−459.21−487.33−28.12
1181-METHYLCYCLOPENTENE−36.44−57.44−21
1192,3-DIMETHYL-1-HEXENE−136−164.84−28.84
1201,4-DI-tert-BUTYLBENZENE−188.9−165.1523.75
121alpha-TOCOPHEROL−873.4−879.94−6.54
1221,2,3-TRIETHYLBENZENE−130.32−111.418.92
123n-HEPTYLBENZENE−140.6−138.272.33
1241,2,3,5-TETRAETHYLBENZENE−196.36−165.1531.21
125n-DECYLBENZENE−217.5−218.9−1.4
126PENTAETHYLBENZENE−258.1−218.939.2
127m-TERPHENYL165.58156.52−9.06
128n-PENTYLBENZENE−89.5−84.524.98
129n-HEXYLBENZENE−115−111.43.6
130n-OCTYLBENZENE−166.1−165.150.95
131n-NONYLBENZENE−190.4−192.02−1.62
132n-UNDECYLBENZENE−241.18−245.77−4.59
133n-TRIDECYLBENZENE−288.73−299.52−10.79
134n-TETRADECYLBENZENE−311.49−326.4−14.91
135n-DODECYLBENZENE−264.79−272.65−7.86
1362,3-DIMETHYL-2,3-DIPHENYLBUTANE−59.68−58.061.62
1371,1,2-TRIPHENYLETHANE130.2102.77−27.43
138TETRAPHENYLMETHANE247.1182.98−64.12
1391,1,2,2-TETRAPHENYLETHANE216156.1−59.9
1401-(4-ETHYLPHENYL)-2-PHENYLETHANE12.03−4.32−16.35
141STYRENE103.4749.75−53.72
1421-n-NONYLNAPHTHALENE−132.57−111.7620.81
1431-n-DECYLNAPHTHALENE−156.26−138.6417.62
1441-n-HEXYL-1,2,3,4-TETRAHYDRONAPHTHALENE−179.33−165.2514.08
1451-PHENYLINDENE148.61129.85−18.76
146TRIPHENYLETHYLENE233.38156.41−76.97
147TETRAPHENYLETHYLENE311.5209.75−101.75
148trans-STILBENE136.9103.08−33.82
149ACENAPHTHALENE186.6183.65−2.95
150sec-BUTYLCYCLOHEXANE−263.7−218.5945.11
151PIMARIC ACID−634.1−611.2922.81
152ISOPIMARIC ACID−670.4−611.2959.11
153SULFUR DIOXIDE−296.84−315.26−18.42
154SULFUR TRIOXIDE−441.04−457.7−16.66
155ACETALDEHYDE−166.4−199.68−33.28
156PROPANAL−215.3−226.56−11.26
1571,2,3,6-TETRAHYDROBENZALDEHYDE−162.1−226.76−64.66
158BUTANAL−239.2−253.43−14.23
159HEPTANAL−311.5−334.06−22.56
160HEXANAL−291.83−307.18−15.35
161OCTANAL−342.7−360.93−18.23
162NONANAL−367.93−387.8−19.87
1632-ETHYLHEXANAL−348.5−360.93−12.43
1642-METHYLHEXANAL−317.47−334.06−16.59
1652-METHYL-2-PENTENAL−201.8−253.54−51.74
1662-ETHYL-2-HEXENAL−244.6−307.28−62.68
167DECANAL−393.84−414.68−20.84
168UNDECANAL−419.06−441.55−22.49
169DODECANAL−445.25−468.43−23.18
1702-METHYLBUTYRALDEHYDE−271.5−280.31−8.81
1713-METHYLBUTYRALDEHYDE−276.5−280.31−3.81
172cis-CROTONALDEHYDE−137.7−199.79−62.09
173trans-CROTONALDEHYDE−138.7−199.79−61.09
174o-TOLUALDEHYDE−113.18−146.35−33.17
175p-HYDROXYBENZALDEHYDE−310.82−315.57−4.75
176TEREPHTHALDEHYDE−243.43−288.8−45.37
1772-METHYL OCTANAL−370.2−387.8−17.6
178METHYL ETHYL KETONE−273.3−253.4319.87
179METHYL ISOBUTYL KETONE−328.4−307.1821.22
1803-METHYL-2-PENTANONE−323.8−307.1816.62
1813-HEPTANONE−348.6−334.0614.54
1824-HEPTANONE−346.2−334.0612.14
1833-HEXANONE−320.2−307.1813.02
1842-HEXANONE−322.01−307.1814.83
185MESITYL OXIDE−238.14−253.54−15.4
1863,3-DIMETHYL-2-BUTANONE−328.6−307.1821.42
187DIISOBUTYL KETONE−408.5−387.820.7
188DIISOPROPYL KETONE−352.92−334.0618.86
1892-PYRROLIDONE−266.04−226.6639.38
190N-METHYL-2-PYRROLIDONE−262.2−253.548.66
191ETHYL ISOAMYL KETONE−374.4−360.9313.47
1925-NONANONE−398.24−387.810.44
1932-NONANONE−396.8−387.89
194ACETYLACETONE−423.8−422.751.05
195CYCLOPENTANONE−235.7−226.669.04
196CYCLOHEXANONE−271.2−253.5417.66
1972-OCTANONE−372.7−360.9311.77
198BENZOPHENONE−37.3−66.14−28.84
199ACETOPHENONE−142.5−146.35−3.85
200beta-PROPIOLACTONE−329.9−369−39.1
2012-CYCLOHEXYL CYCLOHEXANONE−390.98−361.1429.84
202METHANOL−239.1−226.4512.65
203ETHANOL−276.98−253.3323.65
2041-PROPANOL−302.6−280.222.4
205ISOPROPANOL−318.1−280.237.9
2061-BUTANOL−327.2−307.0820.12
2072-BUTANOL−342.6−307.0835.52
2082-METHYL-2-PROPANOL−365.9−307.0858.82
2091-PENTANOL−351.6−333.9517.65
2102-PENTANOL−365.2−333.9531.25
2112-METHYL-1-BUTANOL−356.6−333.9522.65
2122,2-DIMETHYL-1-PROPANOL−382.01−333.9548.06
2131-HEXANOL−377.5−360.8316.67
2142-HEXANOL−392−360.8331.17
2153-METHYL-1-PENTANOL−380.9−360.8320.07
2163-PENTANOL−370.33−333.9536.38
2172-ETHYL-1-HEXANOL−432.8−414.5818.22
2182-METHYL-1-HEXANOL−404.5−387.716.8
2193-METHYL-1-BUTANOL−356.4−333.9522.45
2201-HEPTANOL−403.3−387.715.6
2211-NONANOL−453.6−441.4512.15
2221-DECANOL−478.1−468.329.78
2231-UNDECANOL−504.8−495.29.6
2248-METHYL-1-NONANOL−483.13−468.3214.81
2251-DODECANOL−528.5−522.076.43
2261-TRIDECANOL−599.4−548.9550.45
2271-TETRADECANOL−628.18−575.8252.36
2281-PENTADECANOL−658.2−602.755.5
2291-HEPTADECANOL−722.85−656.4566.4
2302-ETHYL-1-BUTANOL−382.41−360.8321.58
2311-METHYLCYCLOHEXANOL−388.17−334.0654.11
232cis-2-METHYLCYCLOHEXANOL−390.2−334.0656.14
233cis-3-METHYLCYCLOHEXANOL−416.1−334.0682.04
234trans-3-METHYLCYCLOHEXANOL−394.4−334.0660.34
235cis-4-METHYLCYCLOHEXANOL−413.2−334.0679.14
236trans-4-METHYLCYCLOHEXANOL−433.3−334.0699.24
237AGATHADIOL−685.7−718.58−32.88
238alpha-TERPINEOL−316.7−361.03−44.33
2392-BUTYL-NONAN-1-OL−540.1−548.95−8.85
240TETRAHYDROFURFURYL ALCOHOL−435.7−476.4−40.7
2412-PHENYL-2-PROPANOL−244.43−226.8717.56
2422-BUTYL-OCTAN-1-OL−512.2−522.07−9.87
2432,6-XYLENOL−237.4−199.9937.41
244BENZYL ALCOHOL−160.71−173.12−12.41
245m-CRESOL−194−173.1220.88
246o-ETHYLPHENOL−208.82−199.998.83
247p-HYDROQUINONE−371.1−342.3428.76
248p-ETHYLPHENOL−224.39−199.9924.4
249p-tert-BUTYLPHENOL−276.66−253.7422.92
250BISPHENOL A−368.5−369.63−1.13
251NONYLPHENOL−387.33−388.12−0.79
252ETHYLENE GLYCOL−460−449.4210.58
253DIETHYLENE GLYCOL−628.5−699.26−70.76
254TETRAETHYLENE GLYCOL−981.7−1198.95−217.25
2551,2-PROPYLENE GLYCOL−499.99−476.323.69
2561,3-PROPYLENE GLYCOL−480.8−476.34.5
257DIPROPYLENE GLYCOL−718.46−753.01−34.55
2582-METHYL-1,3-PROPANEDIOL−505.9−503.172.73
2591,2-BUTANEDIOL−523.6−503.1720.43
2601,3-BUTANEDIOL−501−503.17−2.17
261HEXYLENE GLYCOL−602.92−556.9246
262GLYCEROL−669.6−672.39−2.79
263p-tert-BUTYLCATECHOL−474−449.8424.16
2642,2,4-TRIMETHYL-1,3-PENTANEDIOL−497.18−610.67−113.49
2652-METHYL-1,3-PENTANEDIOL−577.5−556.9220.58
2662,3-BUTANEDIOL−541.5−503.1738.33
267cis-2-BUTENE-1,4-DIOL−372.9−449.52−76.62
268trans-2-BUTENE-1,4-DIOL−401.6−449.52−47.92
2691,5-PENTANEDIOL−531.49−530.051.44
2701,6-HEXANEDIOL−583.86−556.9226.94
2711,2-BENZENEDIOL−354.1−342.3411.76
2721,3-BENZENEDIOL−368−342.3425.66
273PENTAERYTHRITOL−920.6−922.23−1.63
274TRIMETHYLOLPROPANE−751.61−753.01−1.4
2751,2,3-BENZENETRIOL−551.1−538.4312.67
276SORBITOL−1354.2−1341.2912.91
277FORMIC ACID−425.5−368.956.6
278ACETIC ACID−484.5−395.7888.72
279PROPIONIC ACID−508.5−422.6585.85
280n-DECANOIC ACID−713.7−610.77102.93
281OXALIC ACID−829.7−734.3295.38
282n-BUTYRIC ACID−533.8−449.5284.28
283n-PENTANOIC ACID−558.7−476.482.3
284n-NONANOIC ACID−661.8−583.977.9
285ISOBUTYRIC ACID−531−449.5281.48
286ISOVALERIC ACID−561.6−476.485.2
287n-HEXANOIC ACID−583.8−503.2780.53
2882-METHYLHEXANOIC ACID−613.9−530.1583.75
2891,4-CYCLOHEXANEDICARBOXYLIC ACID−998.5−841.92156.58
290n-OCTANOIC ACID−636.8−557.0279.78
291n-UNDECANOIC ACID−735.9−637.6598.25
292CYCLOPENTYLACETIC ACID−551.73−476.575.23
293DILACTIC ACID−1122.8−1037.9184.89
294n-DODECANOIC ACID−774.6−664.52110.08
295n-HEXADECANOIC ACID−891.5−772.02119.48
296trans-CROTONIC ACID−446.23−395.8850.35
297STEARIC ACID−948−825.77122.23
298ACRYLIC ACID−383.88−36914.88
299OLEIC ACID−802.49−772.1230.37
300LINOLEIC ACID−674.04−718.48−44.44
301SALICYLIC ACID−589.9−511.6678.24
302ADIPIC ACID−994.3−841.82152.48
303MALEIC ACID−789.4−734.4254.98
304TEREPHTHALIC ACID−816.18−680.98135.2
305ACETIC ANHYDRIDE−624.4−591.9732.43
306PROPIONIC ANHYDRIDE−679.1−645.7233.38
307BUTYRIC ANHYDRIDE−719.12−699.4719.65
308PALUSTRIC ACID−852.4−664.94187.46
309SUCCINIC ANHYDRIDE−607.8−538.3369.47
310GLUTARIC ANHYDRIDE−618.5−565.253.3
311PHTHALIC ANHYDRIDE−460.1−431.2428.86
312MALEIC ANHYDRIDE−469.8−484.68−14.88
313TRIMELLITIC ANHYDRIDE−894.81−796.6698.15
314METHYL FORMATE−386.1−395.78−9.68
315n-PROPYL FORMATE−445.2−449.52−4.32
316n-BUTYL FORMATE−469.2−476.4−7.2
317ISOBUTYL FORMATE−475.87−476.4−0.53
318n-PENTYL FORMATE−493.28−503.27−9.99
319n-OCTYL FORMATE−566.45−583.9−17.45
320n-NONYL FORMATE−588.93−610.77−21.84
321n-DECYL FORMATE−613.73−637.65−23.92
322VINYL FORMATE−293.36−369−75.64
323ETHYL ACETATE−478.8−449.5229.28
324n-PROPYL ACETATE−504.32−476.427.92
325n-BUTYL ACETATE−529.2−503.2725.93
326ISOBUTYL ACETATE−536.06−503.2732.79
327ISOPENTYL ACETATE−558.69−530.1528.54
328ALLYL ACETATE−386.3−422.75−36.45
329ISOPROPYL ACETATE−518.8−476.442.4
330sec-BUTYL ACETATE−544.04−503.2740.77
331VINYL ACETATE−349.7−395.88−46.18
332METHYL PROPIONATE−463.3−449.5213.78
333ETHYL PROPIONATE−502.7−476.426.3
334n-PROPYL PROPIONATE−527.5−503.2724.23
335n-BUTYL PROPIONATE−549.9−530.1519.75
336VINYL PROPIONATE−385.46−422.75−37.29
337ETHYL n-BUTYRATE−514.63−503.2711.36
338n-PROPYL ISOBUTYRATE−564.5−530.1534.35
339METHYL ACRYLATE−362.2−395.88−33.68
340ETHYL ACRYLATE−379.59−422.75−43.16
341n-PROPYL ACRYLATE−407.17−449.63−42.46
342n-BUTYL NONANOATE−697.78−691.46.38
343n-BUTYL VALERATE−613.3−583.929.4
344ETHYL ISOVALERATE−570.9−530.1540.75
345METHYL METHACRYLATE−399.13−422.75−23.62
346ETHYL METHACRYLATE−421.34−449.63−28.29
347n-PROPYL METHACRYLATE−446.7−476.5−29.8
348DIOCTYL PHTHALATE−1084.1−1110.98−26.88
349DIISOOCTYL PHTHALATE−1087.3−1110.98−23.68
3501,2-BENZENEDICARBOXYLIC ACID, HEPTYL, NONYL ESTER−1085−1110.98−25.98
351n-PENTYL ACETATE−553−530.1522.85
3522-ETHYLHEXYL ACETATE−627.99−610.7717.22
353BENZYL ACETATE−368.8−369.32−0.52
354ISOBUTYL ISOBUTYRATE−594.07−557.0237.05
355ISOPENTYL ISOVALERATE−644.74−610.7733.97
356METHYL OLEATE−734.5−799−64.5
357n-HEXYL ACETATE−577.9−557.0220.88
358n-BUTYL BENZOATE−429.06−423.075.99
359n-HEPTYL ACETATE−602.67−583.918.77
360n-OCTYL ACETATE−628.25−610.7717.48
361n-DECYL ACETATE−679.25−664.5214.73
362DIISODECYL PHTHALATE−1196.9−1218.48−21.58
363METHYL SALICYLATE−531.79−538.54−6.75
364DI-n-NONYL PHTHALATE−1134.8−1164.73−29.93
365DI-n-PROPYL PHTHALATE−811.89−842.23−30.34
366DIISOBUTYL PHTHALATE−890−895.98−5.98
367DIMETHYL ISOPHTHALATE−730.9−734.73−3.83
368DI-n-DECYL PHTHALATE−1197−1218.48−21.48
369DI-n-UNDECYL PHTHALATE−1248−1325.98−77.98
370DI-n-HEXYL PHTHALATE−987.8−1003.48−15.68
371DIMETHYL TEREPHTHALATE−732.6−734.73−2.13
372DI-n-OCTYL TEREPHTHALATE−1181.2−1110.9870.22
373n-BUTYL STEARATE−978.16−933.2744.89
374DIBUTYL SEBACATE−1156.7−1164.31−7.61
375n-BUTYL n-BUTYRATE−575.39−557.0218.37
376n-BUTYL METHACRYLATE−471.39−503.38−31.99
377METHYL BENZOATE−343.5−342.441.06
378ETHYL BENZOATE−379.91−369.3210.59
379DIETHYL CARBONATE−682.65−672.4910.16
380DIETHYL OXALATE−806.28−841.82−35.54
381DIETHYL MALONATE−838.02−868.69−30.67
382ISOPROPYL MYRISTATE−820.33−798.921.43
383TRI-n-HEPTYL TRIMELLITATE−1697−1610.7786.23
3841,2-BENZENE DICARBOXYLIC ACID, HEPTYL, UNDECYL ESTER−1137−1164.73−27.73
385DIMETHYL ETHER−184.1−253.33−69.23
386DIETHYL ETHER−279.4−307.08−27.68
387DIISOPROPYL ETHER−351.5−360.83−9.33
388DI-n-BUTYL ETHER−377.9−414.58−36.68
389METHYL tert-BUTYL ETHER−313.6−333.95−20.35
390DI-sec-BUTYL ETHER−401.5−414.58−13.08
391METHYL ETHYL ETHER−216.4−280.2−63.8
392METHYL n-PROPYL ETHER−265.89−307.08−41.19
393ISOPROPYL BUTYL ETHER−365.64−387.7−22.06
394METHYL ISOBUTYL ETHER−296.13−333.95−37.82
395DI-n-HEXYL ETHER−481.96−522.07−40.11
396METHYL n-BUTYL ETHER−290.6−333.95−43.35
397ETHYL PROPYL ETHER−303.59−333.95−30.36
3981,4-DIOXANE−355.1−449.52−94.42
399TRIOXANE−522.5−618.74−96.24
400DI-tert-BUTYL ETHER−399.61−414.58−14.97
401DI-n-OCTYL ETHER−582.75−629.57−46.82
402DI-n-PENTYL ETHER−425.12−468.32−43.2
403METHYL sec-BUTYL ETHER−305.24−333.95−28.71
404tert-BUTYL ETHYL ETHER−346.83−360.83−14
405METHYL n-PENTYL ETHER−315.1−360.83−45.73
406ETHYL tert-PENTYL ETHER−369.07−387.7−18.63
407METHYLAL−378.2−476.3−98.1
408ACETAL−491.41−556.92−65.51
409ETHYL ISOBUTYL ETHER−333.5−360.83−27.33
410DI-n-PROPYL ETHER−328.82−360.83−32.01
411n-BUTYL ETHYL ETHER−328.7−360.83−32.13
412DIETHYLENE GLYCOL DI-n-BUTYL ETHER−723.58−914.26−190.68
413BENZYL ETHYL ETHER−165.78−226.87−61.09
414PHENETOLE−152.6−199.99−47.39
4151-METHYL-3-(METHYLETHOXY)BENZENE−221.6−253.74−32.14
4161,1-DIMETHOXYETHANE−420.1−503.17−83.07
4172,5-DIHYDROFURAN−141.36−199.79−58.43
418TETRAHYDROFURAN−216.19−253.43−37.24
4191-tert-BUTOXY-2-[2-(tert-BUTOXY)PROPOXY]PROPANE−810.3−968.01−157.71
4201,2-DIMETHOXYPROPANE−422.3−530.05−107.75
421sec-BUTYL-tert-BUTYL ETHER−417.5−414.582.92
422ISOBUTYL-tert-BUTYL ETHER−407−414.58−7.58
4231,4-DICHLORO-trans-2-BUTENE−112.53−111.091.44
424HEXACHLOROETHANE−202.8−218.48−15.68
4251,1,1,2-TETRACHLOROETHANE−191−164.7326.27
4261,1,2,2-TETRACHLOROETHANE−194.6−164.7329.87
427HEXACHLOROCYCLOPENTADIENE−159.78−138.1721.61
428PENTACHLOROETHANE−187.6−191.61−4.01
4293,4-DICHLORO-1-BUTENE−106.91−111.09−4.18
430DICHLORODIFLUOROMETHANE−491.62−487.374.25
431TRICHLOROFLUOROMETHANE−288.7−312.61−23.91
432CHLOROTRIFLUOROMETHANE−707.93−662.1245.81
4332-CHLORO-1,1,1-TRIFLUOROETHANE−741.8−68952.8
4341,2-DICHLOROTETRAFLUOROETHANE−916.3−917.5−1.2
4351,2-DIBROMOTETRAFLUOROETHANE−807.1−917.5−110.4
436METHYL FLUORIDE−234.3−231.992.31
437DIFLUOROMETHANE−452.3−433.6218.68
438TRIFLUOROMETHANE−697.05−635.2561.8
439CARBON TETRAFLUORIDE−933.15−836.8896.27
440ETHYL FLUORIDE−264.4−258.865.54
4411,1,1-TRIFLUOROETHANE−736.4−662.1274.28
442DECAFLUOROBUTANE−2149.7−2127.2822.42
443PERFLUORO-n-DECANE−4710−4708.081.92
4441,1-DIFLUOROETHYLENE−328.96−406.85−77.89
445TETRAFLUOROETHYLENE−658.56−810.11−151.55
446BROMODIFLUOROMETHANE−424.9−460.49−35.59
4471,1-DIFLUOROETHANE−497−460.4936.51
4481-BROMOPROPANE−121.8−110.9810.82
4491-BROMOBUTANE−143.8−137.865.94
4501-BROMOHEPTANE−218.4−218.48−0.08
4511,2-DIBROMOETHANE−79.2−110.98−31.78
4521,1,1-TRICHLOROTRIFLUOROETHANE−822−742.7579.25
453ISOPROPYL IODIDE−74.8−110.98−36.18
4542,2-DICHLORO-1,1,1-TRIFLUOROETHANE−770.3−715.8754.43
455HEXAFLUOROPROPYLENE−1079−1240.24−161.24
4562-METHYL-2-AMINOBUTANE−171.4−164.736.67
457DI-n-PROPYLAMINE−156.11−191.61−35.5
458DIETHYLAMINE−103.7−137.86−34.16
459n-PROPYLAMINE−101.47−110.98−9.51
460n-PENTYLAMINE−152.62−164.73−12.11
461ISOBUTYLAMINE−132.6−137.86−5.26
462DIISOBUTYLAMINE−218.5−245.36−26.86
463PYRROLE63.1149.9−13.21
464METHYL DIETHANOLAMINE−473.77−556.92−83.15
465DIETHANOLAMINE−493.8−530.05−36.25
466TRIETHANOLAMINE−667.35−779.89−112.54
467sec-BUTYLAMINE−137.49−137.86−0.37
468tert-BUTYLAMINE−150.6−137.8612.74
469CYCLOHEXYLAMINE−147.7−137.969.74
470HEXAMETHYLENEDIAMINE−192.42−218.48−26.06
471DIISOPROPYLAMINE−178.5−191.61−13.11
472DI-n-BUTYLAMINE−206−245.36−39.36
473PIPERIDINE−86.4−111.09−24.69
474QUINOLINE141.22130.11−11.11
475FORMANILIDE−151.46−146.355.11
4761,2-PROPANEDIAMINE−97.8−137.86−40.06
477N-METHYLPYRROLE62.3823.03−39.35
478DIPHENYLAMINE13076.31−53.69
479HYDRACRYLONITRILE−161.2−199.79−38.59
480HYDROGEN CYANIDE108.1950.06−58.13
481ACETONITRILE40.5623.18−17.38
482METHACRYLONITRILE64.7823.08−41.7
483VALERONITRILE−33.1−57.44−24.34
484BENZONITRILE163.18103.39−59.79
485PYRIDINE100.249.85−50.35
486HEXAMETHYLENEIMINE−103.82−137.96−34.14
4872-METHYLPYRIDINE56.722.97−33.73
488tert-BUTYL MERCAPTAN−140.5−137.862.64
489ISOBUTYL MERCAPTAN−132−137.86−5.86
490sec-BUTYL MERCAPTAN−131−137.86−6.86
491n-HEXYL MERCAPTAN−175.7−191.61−15.91
492n-NONYL MERCAPTAN−248.66−272.23−23.57
493n-OCTYL MERCAPTAN−224.47−245.36−20.89
494CYCLOHEXYL MERCAPTAN−140.7−137.962.74
495METHYL ETHYL SULFIDE−91.6−110.98−19.38
496METHYL n-PROPYL SULFIDE−118.5−137.86−19.36
497METHYL t-BUTYL SULFIDE−157.1−164.73−7.63
498DI-n-PROPYL SULFIDE−169.9−191.61−21.71
499ETHYL n-OCTYL SULFIDE−273.3−299.11−25.81
500DIMETHYL SULFIDE−65.4−84.11−18.71
501THIOPHENE80.249.9−30.3
502DIETHYL DISULFIDE−120.1−164.73−44.63
503UNDECYL MERCAPTAN−302.87−325.98−23.11
504n-DECYL MERCAPTAN−276.5−299.11−22.61
505n-PENTYL MERCAPTAN−149.69−164.73−15.04
506DICYCLOHEXYL SULFIDE−241.8−245.56−3.76
507THIAINDAN59.2622.87−36.39
508n-DODECYL MERCAPTAN−327.18−352.86−25.68
509tert-OCTYL MERCAPTAN−245.23−245.36−0.13
510n-HEPTYL MERCAPTAN−200.5−218.48−17.98
511n-BUTYL MERCAPTAN−124.7−137.86−13.16
512TETRAHYDROTHIOPHENE−72.9−84.21−11.31
513DIMETHYL SULFOXIDE−204.2−226.56−22.36
5143-METHYL SULFOLANE−488−395.9892.02
515DI-n-BUTYL SULFONE−609.86−530.2579.61
516ACETYL CHLORIDE−272.8−226.5646.24
517CHLOROACETIC ACID−510.5−422.6587.85
518CHLOROACETYL CHLORIDE−283.7−253.4330.27
519TRICHLOROACETYL CHLORIDE−280.8−307.18−26.38
520BENZOYL CHLORIDE−158−146.3511.65
521p-CHLOROBENZOTRIFLUORIDE−663.63−608.7954.84
5222,4-DICHLOROBENZOTRIFLUORIDE−702.75−635.6667.09
523FLUOROBENZENE−150.6−151.78−1.18
5243-CHLORO-1,2-PROPANEDIOL−525.3−503.1722.13
5251,3-DICHLORO-2-PROPANOL−385.3−333.9551.35
5262,3-DICHLORO-1-PROPANOL−381.5−333.9547.55
527DI(2-CHLOROETHYL)ETHER−356.2−360.83−4.63
5283-(METHYLMERCAPTO)PROPANAL−211.1−280.31−69.21
529TRIFLUOROACETIC ACID−1069.9−1000.6669.24
530GLYCINE−528.1−422.65105.45
5314-METHOXYPHENYLACETIC ACID−578.4−565.4112.99
532N,N-DIMETHYLFORMAMIDE−239.2−253.43−14.23
5332-METHACRYLAMIDE−269.68−226.6643.02
534ACRYLAMIDE−212.08−199.7912.29
535epsilon-CAPROLACTAM−328.5−280.4148.09
536HEXAMETHYL PHOSPHORAMIDE−533.9−414.68119.22
537ACETALDOL−433.62−449.52−15.9
538FURFURAL−201.6−288.64−87.04
539CARBONYL SULFIDE−142−146.04−4.04
540PHOSGENE−218.9−226.56−7.66
541ACETOMETHOXANE−873.7−895.57−21.87
542ETHYLENE GLYCOL DIACRYLATE−662.81−788.27−125.46
543PROPYLENE GLYCOL MONOMETHYL ETHER ACETATE−663.23−699.37−36.14
544DIPROPYLENE GLYCOL MONOMETHYL ETHER ACETATE−878.99−976.09−97.1
545SULFURIC ACID−813.99−707.44106.55
546SULFUR HEXAFLUORIDE−1220.5−1240.14−19.64
547SULFURYL CHLORIDE−394.1−36925.1
548THIONYL CHLORIDE−245.6−226.5619.04
549HEXAMETHYLCYCLOTRISILOXANE−1622−1579.7242.28
550DODECAMETHYLPENTASILOXANE−2621−2577.6143.39
551METHYL VINYL DICHLOROSILANE−380.8−377.663.14
552[3-(MERCAPTO)PROPYL]TRIETHOXYSILANE−1054−1153.96−99.96
5533-(TRIMETHOXYSILYL)-1-PROPANETHIOL−933.1−1073.34−140.24
554OCTAMETHYLCYCLOTETRASILOXANE−2195−2123.0271.98
555GLUTARALDEHYDE−365.87−422.75−56.88
556n-TRIACONTANE−911.03−809.72101.31
557n-DOTRIACONTANE−969.93−863.47106.46
5583-OCTANONE−371.8−360.9310.87
5594-OCTANONE−373.1−360.9312.17
560n-HEXATRIACONTANE−1082.8−970.97111.83
5612-CYCLOHEXENE-1-ONE−170.9−199.89−28.99
5622,3-DIMETHYLOCTANE−304.31−272.2332.08
5632,4-DIMETHYLOCTANE−307.95−272.2335.72
5642,5-DIMETHYLOCTANE−308.42−272.2336.19
5652,6-DIMETHYLOCTANE−307.95−272.2335.72
566m-ETHYLPHENOL−214.3−199.9914.31
5672-PHENYLETHANOL−181.61−199.99−18.38
5682,6-DIMETHYL-4-HEPTANOL−469.54−441.4528.09
5691-PHENYL-1-PROPANOL−219.78−226.87−7.09
5703-PHENYL-1-PROPANOL−217.9−226.87−8.97
571beta-CHOLESTEROL−726.92−656.9769.95
572alpha-METHYLBENZYL ALCOHOL−197.43−199.99−2.56
573o-TOLUALCOHOL−206.7−199.996.71
574m-TOLUALCOHOL−197.3−199.99−2.69
575p-tert-OCTYLPHENOL−392.44−361.2431.2
576p-tert-AMYLPHENOL−300.85−280.6220.23
577p-CUMYLPHENOL−172.25−173.53−1.28
5782,4-PENTANEDIOL−556.35−530.0526.3
5793-METHYL-trans-2-PENTENE−94.56−111.09−16.53
5805-METHYL-1-HEXENE−100−137.96−37.96
581DECAN-1,10-DIOL−699.71−664.4235.29
5821,4-CYCLOHEXANEDIMETHANOL−584.6−557.0227.58
5832-METHYL-1-OCTENE−165.1−191.71−26.61
5842-METHYL-1-HEPTENE−134.18−164.84−30.66
585TRIMELLITIC ACID−1179.2−1046.4132.8
586TRILACTIC ACID−1547−1457.0889.92
587LINOLENIC ACID−526.43−664.83−138.4
588AZELAIC ACID−1059.3−922.44136.86
589NEOPENTANOIC ACID−564−476.487.6
590PENTADECANOIC ACID−861.7−745.15116.55
5912-ETHYL HEXANOIC ACID−635.1−557.0278.08
592n-HEPTANOIC ACID−611.4−530.1581.25
593NEOHEXANOIC ACID−595−503.2791.73
594NEOHEPTANOIC ACID−613.53−530.1583.38
595n-HEPTADECANOIC ACID−924.4−798.9125.5
596NONADECANOIC ACID−984−852.64131.36
597n-EICOSANIC ACID−1011.9−879.52132.38
598FUMARIC ACID−812.2−734.4277.78
599PIMELIC ACID−1009.8−868.69141.11
600SUBERIC ACID−1038−895.57142.43
601CINNAMIC ACID−336.9−315.6721.23
602ACETOXYACETIC ACID−879.7−788.0791.63
603SEBACIC ACID−1082.6−949.31133.29
604ITACONIC ACID−841.1−761.379.8
605SUCCINIC ACID−940.4−788.07152.33
606GLUTARIC ACID−959.9−814.94144.96
607PYROMELLITIC ACID−1570.8−1411.82158.98
608IBUPROFEN−559.53−476.8282.71
609METHYL MALEIC ANHYDRIDE−504.55−511.56−7.01
610sec-BUTYL FORMATE−482.76−476.46.36
611tert-BUTYL FORMATE−499.65−476.423.25
612n-HEXYL FORMATE−518.49−530.15−11.66
613n-HEPTYL FORMATE−542.98−557.02−14.04
614CYCLOHEXYL FORMATE−495.52−476.519.02
615tert-BUTYL ACETATE−561.02−503.2757.75
616METHYL ISOBUTYRATE−501.76−476.425.36
617ETHYL ISOBUTYRATE−538.74−503.2735.47
618ISOPROPYL ACRYLATE−419.4−449.63−30.23
619BENZYL FORMATE−305.13−342.44−37.31
620CETYL METHACRYLATE−742.81−825.87−83.06
621DIMETHYL-2,6-NAPHTHALENEDICARBOXYLATE−709.5−654.4755.03
622CYCLOHEXYL ACETATE−553.48−503.3850.1
623n-NONYL n-UNDECYL PHTHALATE−1140−1218.48−78.48
624DIISONONYL PHTHALATE−1237−1164.7372.27
625DIETHYL PHTHALATE−776.6−788.48−11.88
626DIMETHYL PHTHALATE−677.81−734.73−56.92
627DIETHYL SUCCINATE−913.07−895.5717.5
628DIHEXYL ADIPATE−1161.6−1164.31−2.71
629ETHYLIDENE DIACETATE−865.97−841.8224.15
630DIBUTYL MALEATE−772.2−949.42−177.22
631METHYL DODECANOATE−693−691.41.6
632DIETHYL MALEATE−798.18−841.92−43.74
633DIMETHYL MALEATE−680.85−788.17−107.32
634DIPROPYL MALEATE−785.11−895.67−110.56
635sec-BUTYL ACRYLATE−436.8−476.5−39.7
636VINYL PIVALATE−429.1−476.5−47.4
637DIMETHYL CARBONATE−607.27−618.74−11.47
638n-PROPYL BENZOATE−397.7−396.191.51
639ETHYL ISOPROPYL ETHER−315.8−333.95−18.15
640ETHYL n-HEXYL ETHER−381.01−414.58−33.57
6411,3-DIOXANE−377.5−449.52−72.02
6421,2-DIETHOXYETHANE−451.43−556.92−105.49
6432,3-DICHLOROPROPENE−73.3−84.21−10.91
644n-PENTADECYLBENZENE−335.24−353.27−18.03
645n-HEXADECYLBENZENE−414.67−380.1534.52
646n-HEPTADECYLBENZENE−442.5−407.0235.48
647n-OCTADECYLBENZENE−469.9−433.8936.01
6481,3-DICHLOROHEXAFLUOROPROPANE−1321.8−1347.63−25.83
6491,2-DICHLOROHEXAFLUOROCYCLOBUTANE−1282.7−1320.86−38.16
6503,3,3-TRIFLUOROPROPENE−614.2−635.35−21.15
6511,1,2-TRIFLUOROETHANE−675.9−662.1213.78
652PERFLUORO-n-HEXADECANE−7251−7288.88−37.88
653PERFLUOROMETHYLCYCLOPENTANE−2533−2530.642.36
6541,1,1,2,2-PENTAFLUOROPROPANE−1111−1092.2618.74
6551,1,1,2,3,3-HEXAFLUOROPROPANE−1333−1293.8939.11
656BENZOTRIFLUORIDE−636.7−581.9154.79
6572-BROMOBUTANE−155.1−137.8617.24
658BROMOCHLOROMETHANE−76.01−84.11−8.1
659HALOTHANE−720−715.874.13
6601,2-DIFLUOROETHANE−447.7−460.49−12.79
661PENTACHLOROFLUOROETHANE−382−393.24−11.24
6621,2-DICHLORO-1,1,2-TRIFLUOROETHANE−735.55−715.8719.68
6632-CHLORO-1,1,1,2-TETRAFLUOROETHANE−924.7−890.6334.07
6641,1-DICHLORO-1-FLUOROETHANE−366.4−312.6153.79
6651,1,1,2-TETRAFLUOROETHANE−895.79−863.7532.04
666HEXAFLUOROACETONE−1460−1436.3323.67
667OCTAFLUOROPROPANE−1783.2−1697.1486.06
668OCTAFLUORO-2-BUTENE−1648−1670.37−22.37
669OCTAFLUOROCYCLOBUTANE−1528−1670.37−142.37
6701,1,1-TRICHLOROFLUOROETHANE−337.1−339.49−2.39
6711,1,2,2-TETRAFLUOROETHANE−892.4−863.7528.65
672p-BROMOTOLUENE17.14−3.9−21.04
673n-HEXYL IODIDE−146.4−191.61−45.21
674BROMOTRIFLUOROMETHANE−648.98−662.12−13.14
675DIBROMODIFLUOROMETHANE−386.6−487.37−100.77
676CHLOROTRIFLUOROETHYLENE−555.3−635.35−80.05
677HEXAFLUOROETHANE−1343.9−1267.0176.89
6781-CHLORO-1,1-DIFLUOROETHANE−529.7−487.3742.33
679n-HEXYLAMINE−177.12−191.61−14.49
680n-HEPTYLAMINE−201.33−218.48−17.15
681n-OCTYLAMINE−226.02−245.36−19.34
682n-NONYLAMINE−250.44−272.23−21.79
683n-DECYLAMINE−275.19−299.11−23.92
684n-DODECYLAMINE−368.18−352.8615.32
685CYCLOHEXYL ISOCYANATE−200.64−253.64−53
686N,N′-DI-tert-BUTYLETHYLENEDIAMINE−264.9−325.98−61.08
687DICYCLOHEXYLAMINE−246.4−245.560.84
688N-METHYLCYCLOHEXYLAMINE−149.52−164.84−15.32
689N-AMINOETHYL ETHANOLAMINE−280.19−360.83−80.64
690PHENYL ISOCYANATE−61.08−92.7−31.62
691ISOQUINOLINE134.2130.11−4.09
692p-AMINODIPHENYL8176.31−4.69
6932,6-DIETHYLANILINE−84.23−84.52−0.29
6943-METHYLPYRIDINE61.922.97−38.93
6954-METHYLPYRIDINE59.222.97−36.23
696ETHYL t-BUTYL SULFIDE−187.3−191.61−4.31
697tert-NONYL MERCAPTAN−266.22−272.23−6.01
6982-METHYLTHIOPHENE44.623.03−21.57
6993-METHYLTHIOPHENE43.123.03−20.07
700CAMPHOR−319.4−307.3912.01
701N-METHYLFORMAMIDE−241.48−226.5614.92
702DIACETONE ALCOHOL−592.79−503.2789.52
703FURFURYL ALCOHOL−276.2−342.29−66.09
704N,N-DIMETHYLACETAMIDE−278.3−280.31−2.01
705ACETAMINOPHEN−396.04−369.3226.72
706p-METHOXYPHENOL−335.51−369.21−33.7
7072-METHOXYETHANOL−416.32−476.3−59.98
7082-ETHOXYETHANOL−448.22−503.17−54.95
7092-BUTOXYETHANOL−497.4−556.92−59.52
7102-(2-METHOXYETHOXY)ETHANOL−589.99−726.14−136.15
7112-(2-ETHOXYETHOXY)ETHANOL−626.28−753.01−126.73
7122-AMINOETHOXYETHANOL−438.01−530.05−92.04
713ETHYLCHLOROACETATE−509.3−476.432.9
7142-(2-(2-METHOXYETHOXY)ETHOXY)ETHANOL−786.4−975.98−189.58
715SUCCINIMIDE−460.25−369.1191.14
7164-CARBOXYBENZALDEHYDE−544.91−484.8960.02
717THIOGLYCOLIC ACID−454.56−422.6531.91
7182-HYDROXYETHYL METHACRYLATE−576.15−645.72−69.57
719METHYL LACTATE−643.1−645.62−2.52
7202-METHOXY PROPANOL-1−449.47−503.17−53.7
721alpha-METHYLBENZYL ALCOHOL FORMATE−347.1−369.32−22.22
7222-FORMYL BENZOIC ACID−531.54−484.8946.65
7232-HYDROXYACETOPHENONE−342.2−342.44−0.24
7244-HYDROXYACETOPHENONE−364.3−342.4421.86
7254-HYDROXYSTYRENE−109.67−146.35−36.68
726ACETYLSALICYLIC ACID−815.6−707.86107.74
727p-PHENETIDINE−172.6−226.87−54.27
728ACETOL−414.15−422.65−8.5
729o-CHLOROPHENOL−172.35−173.12−0.77
7301-ISOPROPOXY-2-PROPANOL−529.6−556.92−27.32
731ISOPHTHALOYL CHLORIDE−367.5−342.5524.95
7324-FORMYLMORPHOLINE−369.9−449.63−79.73
733FLUOSULFONIC ACID−795.78−712.9882.8
734CHLOROSULFONIC ACID−651.14−538.22112.92
735FERRIC OXIDE−825.5−1071.38−245.88
736ZINC SULFATE−980.14−947.2532.89
7373-ETHYL HEPTANAL−369.5−387.8−18.3
738DIAMYL KETONE−446.5−441.554.95
7392-BUTYL-1-DECANOL−567.6−575.82−8.22
7402-METHYL-1-TRIDECANOL−566.9−575.82−8.92
7412-METHYL-DODECAN-1-OL−552.6−548.953.65
7424-METHYL-1-OCTANOL−462.6−441.4521.15
7433-ETHYL-1-HEPTANOL−440.7−441.45−0.75
744THYMOL−277.9−253.7424.16
7451-METHYL-3-HYDROXY-5-ISOPROPYL BENZENE−300−253.7446.26
7461-METHYL-3-HYDROXY-6-ISOPROPYL BENZENE−295−253.7441.26
747trans-1,8-TERPIN−706.9−610.7796.13
7487-METHYL-1-OCTENE−154.5−191.71−37.21
7492-METHYL-1-NONENE−188.7−218.59−29.89
7508-METHYL-1-NONENE−180.2−218.59−38.39
751trans-2-DECENE−187.1−218.59−31.49
752cis-2-DODECENE−233.7−272.34−38.64
753trans-2-DODECENE−239−272.34−33.34
754CYCLOPROPANE CARBOXYLIC ACID−396.5−395.880.62
755MALONIC ACID−891−761.19129.81
756n-CROTYL ACETATE−410.1−449.63−39.53
757sec-BUTENYL ACETATE−409−449.63−40.63
758VINYLETHYLENE CARBONATE−555.4−565.2−9.8
759DIOCTYL ADIPATE−1266−1271.81−5.81
760DI(2-ETHYLHEXYL)ADIPATE−1265.3−1271.81−6.51
761DODECYL BROMIDE−344.7−352.86−8.16
7621,2-DIBROMODODECANE−367.8−379.73−11.93
763TRIFLUOROIODOMETHANE−589.1−662.12−73.02
764DIFLUOROMETHYL TRIFLUOROMETHYL ETHER−1316−1261.4754.53
765CYCLOPROPANECARBOXAMIDE−190.5−226.66−36.16
7666-AMINOHEXANAMIDE−400.7−360.9339.77
767HEXANAMIDE−423.1−334.0689.04
768TRI-n-OCTYLAMINE−585.01−675.35−90.34
769DIAMYLAMINE−262.21−299.11−36.9
770TRIAMYLAMINE−366.82−433.48−66.66
771UNDECYLAMINE−299.52−325.98−26.46
772NIACIN−344.9−315.5729.33
773L-PHENYLALANINE−466.9−396.1970.71
774DI-2-ETHYLHEXYLAMINE−415.9−460.35−44.45
775BENZIDINE70.749.43−21.27
776DICYANDIAMIDE24.9−3.8−28.7
777DI-tert-BUTYL DISULFIDE−253−272.23−19.23
778DI-tert-BUTYL SULFIDE−232.3−245.36−13.06
7792-METHYLTHIACYCLOPENTANE−105−111.09−6.09
780METHYL ISOPROPYL SULFIDE−123.5−137.86−14.36
7812-ETHYLTHIOPHENE16.61−3.85−20.46
7822-n-PROPYLTHIOPHENE−8.96−30.72−21.76
783ETHYL PROPYL DISULFIDE−146.2−191.61−45.41
784DIISOPENTYLSULFIDE−282−299.11−17.11
785ETHYLENE GLYCOL 2-ETHYLHEXYL ETHER−597.87−637.54−39.67
786PROPYLENE GLYCOL ETHYL ETHER ACETATE−608.2−726.24−118.04
787DIPROPYLENE GLYCOL t-BUTYL ETHER−801.39−860.51−59.12
788DICHLOROACETIC ACID−496.3−449.5246.78
789PROPYLENE GLYCOL MONOMETHYL ETHER−447.74−503.17−55.43
790DIPROPYLENE GLYCOL MONOMETHYL ETHER−660.85−779.89−119.04
791PROPYLENE GLYCOL 1-tert-BUTYL ETHER−610.36−583.7926.57
792TRIPROPYLENE GLYCOL MONOMETHYL ETHER−884.09−1056.61−172.52
793DIETHYLENE GLYCOL MONOPROPYL ETHER−647.93−779.89−131.96
7942-(2-(2-BUTOXYETHOXY)ETHOXY)ETHANOL−844.47−1056.61−212.14
7952-(2-(2-ETHOXYETHOXY)ETHOXY)ETHANOL−796.01−1002.86−206.85
7962-HEXOXYETHANOL−560.3−610.67−50.37
797MONOOLEIN−1175−1244.94−69.94
798PROPYLENE GLYCOL n-PROPYL ETHER−506−556.92−50.92
799DIETHYLENE GLYCOL MONOBUTYL ETHER ACETATE−883.71−1002.96−119.25
8003-HYDROXY-2-METHYL PROPIONALDEHYDE−427.87−476.4−48.53
801HYDROXYACETONITRILE−141.77−172.91−31.14
802DIOLEIN−1670−1817.48−147.48
803TRIOLEIN−2161−2390.03−229.03
804sec-BUTENYL GLYCOL ETHER−385.3−503.27−117.97
805SUCROSE−2226.1−2375.72−149.62
806PENTAFLUOROETHYL TRIFLUOROVINYL ETHER−1900−1866.4733.53
807TRIFLUOROMETHYL TRIFLUOROVINYL ETHER−1521−1463.157.9
808DIPROPYLENE GLYCOL MONOETHYL ETHER−721.6−806.76−85.16
809TRIPROPYLENE GLYCOL MONOETHYL ETHER−957.4−1083.48−126.08
8101-ETHOXY-2-PROPANOL−492.7−530.05−37.35
8111-tert-BUTOXY-2-[2-(HYDROXY)PROPOXY]PROPANE−774.9−860.51−85.61
812METHYL GLYCOLATE−609.4−618.74−9.34
813tert-BUTYL METHACRYLATE−498.2−557.02−58.82
814gamma-AMINOPROPYLTRIETHOXYSILANE−1022−1153.96−131.96
815(3-METHYLACRYLOXYPROPYL)TRICHLOROSILANE−921−850.5870.42
816METHYL DICHLOROSILANE−435.55−377.5657.99
817FERROUS CHLORIDE−341.83−350.69−8.86
818FERRIC CHLORIDE−399.41−377.5621.85
819DIMETHYLCHLOROSILANE−326.35−377.56−51.21
820TRIMETHYLCHLOROSILANE−382.61−404.43−21.82
821DIMETHYLDICHLOROSILANE−480.4−404.4375.97
822DIPHENYLDICHLOROSILANE−238−244.02−6.02
823DICHLORODIETHYLSILANE−530.7−458.1872.52
824ACETOVANILLONE−529.56−565.41−35.85
825VANILLIN−453.4−538.54−85.14
826DIGLYCOLIC ACID−1080.4−984.1696.24
827LEVULINIC ACID−697.05−618.8578.2
828MALIC ACID−1105.4−984.16121.24
829GUAIACOL−325.78−369.21−43.43
830ETHYLENE GLYCOL MONOPROPYL ETHER−473.09−530.05−56.96
8312-(2-BUTOXYETHOXY)ETHANOL−674.4−806.76−132.36
832ETHYLENEDIAMINETETRAACETIC ACID−1759.5−1680.1579.35
833TRICHLOROACETALDEHYDE−234.5−280.31−45.81
834TRICHLOROACETIC ACID−503.3−476.426.9
835CHLOROACETALDEHYDE−252.69−226.5626.13
836DICHLOROACETALDEHYDE−218.07−253.43−35.36
837ETHYL CHLOROFORMATE−505.2−449.5255.68
838METHOXYACETIC ACID−627.04−618.748.3
839METHYL CHLOROFORMATE−460.74−422.6538.09
840DEXTROSE−1273.3−1287.65−14.35
841VINYLTRIMETHOXYSILANE−835.9−965.94−130.04
842TRIMETHOXYSILANE−833−965.84−132.84
843TRIMETHYL SILANOL−545.2−573.65−28.45
844ETHYL ALUMINUM SESQUICHLORIDE−970.6−832.26138.34
845SULFAMIC ACID−674.88−538.22136.66
846BIS(CHLOROMETHYL)ETHER−280.58−307.08−26.5
8473-AMINO-1-PROPANOL−291.34−307.08−15.74
8481-AMINO-2-PROPANOL−294.1−307.08−12.98
849ETHYL THIOLACETATE−231.1−280.31−49.21
850ACETOACETANILIDE−403.33−369.4233.91
851LYSINE−678.69−557.02121.67
852DIMETHYL SULFATE−735.5−761.19−25.69
853DIETHYL SULFATE−813.2−814.94−1.74
854L-GLUTAMIC ACID−1009.7−841.82167.88
855ASCORBIC ACID−1164.6−1180.36−15.76
8566-HYDROXYHEXANOIC ACID−779.32−699.3779.95
857CITRIC ACID−1543.8−1376.45167.35
858LACTIC ACID−682.96−618.7464.22
859TARTARIC ACID−1289.5−1180.25109.25
860HYDROXYCAPROIC ACID−794.19−699.3794.82
861ETHYL LACTATE−695.08−672.4922.59
8622-ETHOXYETHYL ACETATE−663−699.37−36.37
863DIETHYLENE GLYCOL ETHYL ETHER ACETATE−833.64−949.21−115.57
864METHYL ACETOACETATE−642.4−618.8523.55
865ETHYL ACETOACETATE−612.24−645.72−33.48
866METHYL CYANOACETATE−298.3−369.11−70.81
867ETHYL CYANOACETATE−386.49−395.98−9.49
868ETHYL HYDROGEN SULFATE−887.3−761.19126.11
869ACRYLOXY PROPIONIC ACID−786.6−788.17−1.57
870THIODIGLYCOL−477.92−530.05−52.13
8712-MERCAPTOETHANOL−248.94−280.2−31.26
872ETHYLTHIOETHANOL−290.46−333.95−43.49
873DIETHYLETHANOLAMINE−309.5−387.7−78.2
874DIMETHYLETHANOLAMINE−256.97−333.95−76.98
875DIISOPROPANOLAMINE−572.82−583.79−10.97
8763-METHOXYISOPROPYLAMINE−256.2−333.95−77.75
877ETHYLENE GLYCOL MONOBUTYL ETHER ACETATE−710.3−753.12−42.82
878ETHYL VANILLIN−532.3−565.41−33.11
8792-HYDROXYETHYL ACRYLATE−559.87−618.85−58.98
880ETHYL-3-ETHOXYPROPIONATE−684.7−726.24−41.54
881BIS-(2-HYDROXYETHYL) TEREPHTHALATE−1200−1180.6719.33
882DI-(2-CHLOROETHOXY)METHANE−536.2−583.79−47.59
8831-METHYLVINYL ACETATE−390.1−422.75−32.65
8842-PENTOXYETHANOL−528.2−610.67−82.47
8851-CHLORO-3-PROPANOL−343.7−307.0836.62
886TRIFLUOROACETAMIDE−935.3−831.45103.85
887DILACTIDE (dl)−792.1−788.173.93
8882-(2-PENTOXYETHOXY)ETHANOL−725.7−833.64−107.94
889METHYL-4-FORMYLBENZOATE−476.1−511.76−35.66
890HYDROXYPIVALYL HYDROXYPIVALATE−1003−1002.960.04
891TETRAETHYLENE GLYCOL MONOBUTYL ETHER−1032−1306.45−274.45
892METHYL para-TOLUATE−390.7−369.3221.38
Table 4. The predicted ΔHf° by the Eq. (2) for test set as an excluded data set.
Table 4. The predicted ΔHf° by the Eq. (2) for test set as an excluded data set.
IDNameΔHf° (kJ/mol)Res

DIPPR 801Calculated from Eq. (2)
12-METHYLPENTANE−204.64−164.7339.91
22-METHYLHEXANE−229.49−191.6137.88
3n-OCTANE−249.78−218.4831.3
43-METHYLHEPTANE−252.34−218.4833.86
52,5-DIMETHYLHEXANE−260.37−218.4841.89
63,4-DIMETHYLHEXANE−251.83−218.4833.35
72,2,3,3-TETRAMETHYLBUTANE−268.61−218.4850.13
82,2,5-TRIMETHYLHEXANE−293.3−245.3647.94
92,2,3,4-TETRAMETHYLPENTANE−277.7−245.3632.34
102,3,3,4-TETRAMETHYLPENTANE−277.9−245.3632.54
112,2,3,3-TETRAMETHYLHEXANE−303.47−272.2331.24
12n-HEPTADECANE−479.86−460.3519.51
132,2-DIMETHYLOCTANE−313.12−272.2340.89
14n-EICOSANE−623.61−540.9882.63
15n-TETRACOSANE−739.31−648.4890.83
163-METHYLNONANE−303.59−272.2331.36
174-METHYLNONANE−304.1−272.2331.87
182-METHYLOCTANE−280.6−245.3635.24
19ISOPROPYLCYCLOPENTANE−190.09−164.8425.25
20n-BUTYLCYCLOPENTANE−214.2−191.7122.49
21n-BUTYLCYCLOHEXANE−263.09−218.5944.5
22BICYCLOHEXYL−273.7−218.6955.01
23cis-2-PENTENE−53.49−84.21−30.72
24trans-2-PENTENE−57.98−84.21−26.23
252-METHYL-2-BUTENE−68.07−84.21−16.14
26trans-3-HEXENE−86.06−111.09−25.03
273-METHYL-cis-2-PENTENE−94.47−111.09−16.62
282,3-DIMETHYL-2-BUTENE−102.42−111.09−8.67
294-METHYL-1-HEPTENE−126.1−164.84−38.74
30trans-2-OCTENE−135−164.84−29.84
312,4,4-TRIMETHYL-2-PENTENE−142.42−164.84−22.42
321-DECENE−172.3−218.59−46.29
331-PENTADECENE−301.12−352.96−51.84
341-HEPTADECENE−349.83−406.71−56.88
351-NONADECENE−399.59−460.46−60.87
36p-tert-BUTYL ETHYLBENZENE−131.46−111.420.06
37m-DIISOPROPYLBENZENE−132.4−111.421
381,2,4-TRIETHYLBENZENE−134.05−111.422.65
39HEXAETHYLBENZENE−329.6−272.6556.95
40p-TERPHENYL150.25156.526.27
41TRIPHENYLMETHANE171.2129.64−41.56
422-METHYLINDENE60.7849.64−11.14
43INDENE110.4276.52−33.9
44PENTANAL−267.3−280.31−13.01
453-METHYLHEXANAL−315.39−334.06−18.67
46TRIDECANAL−470.62−495.3−24.68
47GLYCOL ALDEHYDE−404.2−395.788.42
48METHACROLEIN−145.04−199.79−54.75
49p-TOLUALDEHYDE−120.56−146.35−25.79
50BENZALDEHYDE−86.82−119.47−32.65
51SALICYLALDEHYDE−265.7−315.57−49.87
52m-TOLUALDEHYDE−123.4−146.35−22.95
53PARALDEHYDE−673.2−699.37−26.17
54ACETONE−248.1−226.5621.54
553-PENTANONE−296.51−280.3116.2
565-HEXEN-2-ONE−197.4−253.54−56.14
572-PENTANONE−297.29−280.3116.98
58METHYL ISOPROPYL KETONE−299.5−280.3119.19
592-HEPTANONE−348.2−334.0614.14
605-METHYL-2-HEXANONE−350.93−334.0616.87
61ISOPHORONE−301.4−280.5120.89
62gamma-BUTYROLACTONE−420.9−395.8825.02
63epsilon-CAPROLACTONE−477.36−449.6327.73
64gamma-VALEROLACTONE−461.3−422.7538.55
65ETHYL ISOPROPYL KETONE−325.9−307.1818.72
66METHYL ISOPROPENYL KETONE−216.79−226.66−9.87
672-METHYL-1-PROPANOL−334.7−307.0827.62
682-METHYL-2-BUTANOL−379.5−333.9545.55
692-METHYL-1-PENTANOL−383.8−360.8322.97
703-METHYL-3-PENTANOL−404.93−360.8344.1
713-METHYL-2-BUTANOL−366.64−333.9532.69
722-HEPTANOL−410.72−387.723.02
735-METHYL-1-HEXANOL−404.31−387.716.61
744-METHYL-2-PENTANOL−394.7−360.8333.87
751-OCTANOL−426.5−414.5811.92
762-OCTANOL−442.92−414.5828.34
772-NONANOL−467.91−441.4526.46
781-HEXADECANOL−686.3−629.5756.73
791-OCTADECANOL−750−683.3266.68
801-EICOSANOL−827−737.0789.93
811-NONADECANOL−785.33−710.275.13
82CYCLOHEXANOL−348.6−307.1841.42
83trans-2-METHYLCYCLOHEXANOL−416.1−334.0682.04
84L-MENTHOL−479.43−414.6864.75
85beta-TERPINEOL−369.2−361.038.17
862-METHYL-1-UNDECANOL−514.5−522.07−7.57
87ALLYL ALCOHOL−171.1−226.56−55.46
882,4-XYLENOL−228.78−199.9928.79
89p-CRESOL−199.28−173.1226.16
90TRIETHYLENE GLYCOL−804.2−949.11−144.91
91NEOPENTYL GLYCOL−551.2−530.0521.15
92TRIPROPYLENE GLYCOL−921.41−1029.73−108.32
931,2,3-BUTANETRIOL−764.1−699.2664.84
941,2,4-BUTANETRIOL−745.1−699.2645.84
951,4-BUTANEDIOL−503.3−503.170.13
96INOSITOL−1362.1−1287.6574.45
972-METHYLBUTYRIC ACID−554.5−476.478.1
98n-TRIDECANOIC ACID−806.6−691.4115.2
99n-TETRADECANOIC ACID−833.5−718.27115.23
100cis-CROTONIC ACID−347.27−395.88−48.61
1012-METHYLOCTANOIC ACID−661.6−583.977.7
102METHACRYLIC ACID−408.09−395.8812.21
103BENZOIC ACID−385.2−315.5769.63
104o-TOLUIC ACID−416.5−342.4474.06
105PHTHALIC ACID−782.07−680.98101.09
106ISOPHTHALIC ACID−803−680.98122.02
107ETHYL FORMATE−420.5−422.65−2.15
108METHYL ACETATE−445.8−422.6523.15
109n-PROPYL n-BUTYRATE−554.1−530.1523.95
110METHYL n-BUTYRATE−490−476.413.6
111n-BUTYL ACRYLATE−433.45−476.5−43.05
112BENZYL BENZOATE−273.1−289.11−16.01
113ETHYLENE CARBONATE−586.3−565.121.2
114n-NONYL ACETATE−654.12−637.6516.47
1152-ETHYLHEXYL ACRYLATE−526.06−584−57.94
116ETHYLENE GLYCOL DIACETATE−865.43−841.8223.61
117ISOBUTYL METHACRYLATE−465.16−503.38−38.22
118METHYL DECANOATE−640.5−637.652.85
119DIMETHYL-1,4-CYCLOHEXANEDICARBOXYLATE−948.9−895.6753.23
120METHYL ISOPROPYL ETHER−278.7−307.08−28.38
121METHYL tert-PENTYL ETHER−339.86−360.83−20.97
122ISOPROPYL ISOBUTYL ETHER−370.63−387.7−17.07
123DIETHYLENE GLYCOL DIETHYL ETHER−638.4−806.76−168.36
1242,3,4,5,2′,3′,4′,5′-OCTAHYDRO-BIFURYL-(3,3′)−390.5−503.38−112.88
125CARBON TETRACHLORIDE−128.41−137.86−9.45
1263-CHLOROPROPENE−30.8−57.34−26.54
1271,4-DICHLORO-cis-2-BUTENE−105.65−111.09−5.44
128m-CHLOROBENZOYL CHLORIDE−189.7−173.2216.48
1291,3-DICHLORO-trans-2-BUTENE−122.25−111.0911.16
130CHLOROFLUOROMETHANE−264−258.865.14
131CHLORODIFLUOROMETHANE−481.6−460.4921.11
1322-CHLORO-1,1-DIFLUOROETHYLENE−329−433.72−104.72
133PERFLUORO-n-OCTANE−3860−3847.8112.19
134METHYL BROMIDE−37.7−57.23−19.53
135PENTAFLUOROETHANE−1100.4−1065.3835.02
136BROMOBENZENE60.722.97−37.73
1371,1-DICHLOROTETRAFLUOROETHANE−926.8−917.59.3
138DICHLOROFLUOROMETHANE−283.3−285.74−2.44
1391-BROMONAPHTHALENE116.39103.23−13.16
140n-BUTYLAMINE−127.7−137.86−10.16
141ISOPROPYLAMINE−112.3−110.981.32
142n-TETRADECYLAMINE−424.7−406.618.1
143MONOETHANOLAMINE−274.47−280.2−5.73
144HEXANENITRILE−57.29−84.32−27.03
145ETHYL MERCAPTAN−73.6−84.11−10.51
146n-PROPYL MERCAPTAN−99.9−110.98−11.08
147ISOPROPYL MERCAPTAN−105.9−110.98−5.08
148METHYL t-PENTYL SULFIDE−179.99−191.61−11.62
149DIETHYL SULFIDE−119.4−137.86−18.46
150DI-n-PROPYL DISULFIDE−171.5−218.48−46.98
151PHENYL MERCAPTAN63.722.97−40.73
152SULFOLANE−441.64−369.1172.53
153CARBONYL FLUORIDE−638.9−576.0762.83
154DICHLOROACETYL CHLORIDE−280.4−280.310.09
155CHLOROMETHYL METHYL ETHER−236−280.2−44.2
1566-AMINOHEXANOL−400−387.712.3
1573-MERCAPTOPROPIONIC ACID−468.36−449.5218.84
158o-CHLOROBENZOIC ACID−404.83−342.4462.39
159ACETONE CYANOHYDRIN−196.28−226.66−30.38
160DICHLOROSILANE−320.49−350.69−30.2
161BIS[3-(TRIETHOXYSILYL)PROPYL]DISULFIDE−2158−2304.44−146.44
1623-NONANONE−397.4−387.89.6
1634-NONANONE−398.3−387.810.5
1642,6,8-TRIMETHYL-4-NONANONE−490.9−468.4322.47
1652,7-DIMETHYLOCTANE−311.3−272.2339.07
1661-PHENYL-2-PROPANOL−220.17−226.87−6.7
1672-PHENYL-1-PROPANOL−223−226.87−3.87
168p-TOLUALCOHOL−209.27−199.999.28
169DINONYLPHENOL−682.28−629.9952.29
170CITRACONIC ACID−824.46−761.363.16
1712-ETHYL BUTYRIC ACID−599.99−503.2796.72
172PROPYLENE CARBONATE−613.2−591.9721.23
173GLYCERYL TRIACETATE−1330.8−1260.9869.82
174DI-n-BUTYL PHTHALATE−842.6−895.98−53.38
175ISOBUTYL ACRYLATE−438.95−476.5−37.55
176DIISOBUTYL ETHER−387.92−414.58−26.66
177ETHYLAL−450.41−530.05−79.64
178PERFLUORO-n-PENTANE−2608−2557.4150.59
179PERFLUORO-n-HEPTANE−3338−3417.68−79.68
1801,1,1,2,3,3,3-HEPTAFLUOROPROPANE−1552−1495.5156.49
1812,2-DICHLORO-1,1,2-TRIFLUOROETHANE−728.38−715.8712.51
1821,1,2-TRICHLOROTRIFLUOROETHANE−805.8−742.7563.05
183BROMOCHLORODIFLUOROMETHANE−431.37−487.37−56
184CHLOROPENTAFLUOROETHANE−1123−1092.2630.74
185CYCLOPENTYLAMINE−95.14−111.09−15.95
186N,N′-DIPHENYL-p-PHENYLENEDIAMINE169.08102.77−66.31
187ISOPHORONE DIISOCYANATE−429−503.69−74.69
188METHYL n-BUTYL SULFIDE−142.9−164.73−21.83
189tert-DODECYL MERCAPTAN−338.83−352.86−14.03
190TRIACETONE ALCOHOL−690.06−779.99−89.93
1914-HYDROXYBUTYRALDEHYDE−417.22−449.52−32.3
1922,2,4-TRIMETHYL-1,3-PENTANEDIOL MONOISOBUTYRATE−903−860.6242.38
193p-CHLOROPHENOL−197.7−173.1224.58
1942-CHLOROETHANOL−307.85−280.227.65
195CHROMIUM TRIOXIDE−578.23−724.28−146.05
196FERROUS SULFATE−928.85−947.25−18.4
197ZINC OXIDE−347.82−439.38−91.56
1986-METHYL-1-OCTANOL−463.5−441.4522.05
199cis-1,8-TERPIN−709.6−610.7798.83
200cis-2-DECENE−182.9−218.59−35.69
2012,2,4-TRIMETHYL-1,3-PENTANEDIOL DIISOBUTYRATE−1118−1110.567.44
202DIMETHYL SUCCINATE−845.1−841.823.28
203BENZENE-1,2,4-TRICARBOXYLIC ACID TRIMETHYL ESTER−1055−1127.02−72.02
204DIMETHYLMALONATE−784.8−814.94−30.14
205DIFLUOROMETHYL METHYL ETHER−642.8−656.59−13.79
206DI-n-OCTYLAMINE−407.3−460.35−53.05
2072-PENTANETHIOL−151.6−164.73−13.13
208DI-n-BUTYL SULFIDE−220.5−245.36−24.86
209PROPYLENE GLYCOL 2-tert-BUTYL ETHER−573.91−583.79−9.88
2102-(2-HEXOXYETHOXY)ETHANOL−742.7−860.51−117.81
211DIPROPYLENE GLYCOL n-PROPYL ETHER−737.7−833.64−95.94
212CROTYL GLYCOL ETHER−386.6−503.27−116.67
213DIETHYLSULFITE−600.43−672.49−72.06
214DIMETHYLDIMETHOXYSILANE−715.46−796.62−81.16
215PYRUVIC ACID−581.41−565.116.31
216METHYL CHLOROACETATE−495.6−449.5246.08
217PERFLUOROBUTANOIC ACID−1924−1860.9363.07
218TRIDECAFLUOROHEPTANOIC ACID−3215−3151.3363.67
219tert-BUTYLFORMAMIDE−340.98−307.1833.8
220METHYLETHANOLAMINE−254.59−307.08−52.49
2212-HYDROXYPROPYL METHACRYLATE−629.34−530.1599.19
2222-HYDROXYPROPYL ACRYLATE−582.5−645.72−63.22
223METHOXYACETONE−383.4−449.52−66.12

Acknowledgment

The authors gratefully acknowledge Mr. Reza Barzin from University of California (San Diego) for his helps, in this project.

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Vatani, A.; Mehrpooya, M.; Gharagheizi, F. Prediction of Standard Enthalpy of Formation by a QSPR Model. Int. J. Mol. Sci. 2007, 8, 407-432. https://doi.org/10.3390/i8050407

AMA Style

Vatani A, Mehrpooya M, Gharagheizi F. Prediction of Standard Enthalpy of Formation by a QSPR Model. International Journal of Molecular Sciences. 2007; 8(5):407-432. https://doi.org/10.3390/i8050407

Chicago/Turabian Style

Vatani, Ali, Mehdi Mehrpooya, and Farhad Gharagheizi. 2007. "Prediction of Standard Enthalpy of Formation by a QSPR Model" International Journal of Molecular Sciences 8, no. 5: 407-432. https://doi.org/10.3390/i8050407

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