Int. J. Mol. Sci.

2007, 8, 407-432
International Journal of
Molecular Sciences
ISSN 1422-0067
© 2007 by MDPI
www.mdpi.org/ijms/
Full Research Paper

Prediction of Standard Enthalpy of Formation by a QSPR Model

Ali Vatani, Mehdi Mehrpooya* and Farhad Gharagheizi

Department of Chemical Engineering, Faculty of Engineering, University of Tehran,

P.O.Box: 11365-4563, Tehran, Iran.

* Author to whom correspondence should be addressed; E-mail: m.mehrpooya@gmail.com

Received: 1 March 2007 / Accepted: 27 March 2007 / Published: 22 May 2007

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 ( R 2 = 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.

Keywords: QSPR; Enthalpy of formation; GA-MLR.

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, ∆H f is an important fundamental physical property of compounds which is defined as
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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.
Int. J. Mol. Sci. 2007, 8 408

∆H reaction = ∑ ∆H f − ∑ ∆H f (1)
p r

where ∆H reaction , ∑ ∆H f , and ∑ ∆H f are standard enthalpy change of reaction, standard enthalpies of
p r

formation of the products, and standard enthalpies of formation of the reactants, respectively.
There are many methods for calculation of ∆H f in the literature, but of them, only three methods
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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 [4-5]. 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 ∆H f of 1115 organic compounds is presented.
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These 1115 compounds belong to all families of materials, as a result the obtained model can be
applied for prediction of ∆H f for any compound.
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2. Procedures and Methods

2.1. Data set

Many compilations for ∆H f have been published in the literature, but of them, we selected the
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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 ∆H f of them were extracted from this database.
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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
Int. J. Mol. Sci. 2007, 8 409

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 [10-12]. 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:

∆H f = 50.1688 − 80.52012nSK + 5364546 SCBO − 169.21889 SCBO − 174.75477 nF

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(2)
− 266.57659nHM

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: R 2 = 0.9830 , F = 10239 .02 ,
s = 58.541 , Q 2 = 0.9826 , where R 2 is the squared correlation coefficient, F is the Fisher factor, s is
the standard deviation, and Q 2 is the squared cross validated correlation coefficient. The statistical
parameters of coefficients of the Eq. (2) are presented in the Table 2.
Int. J. Mol. Sci. 2007, 8 410

Table 1. The molecular descriptors of Eq. (2) and their meaning.

Variable Molecular descriptor meaning

nSK Number of non-H atoms

SCBO Sum of conventional bond orders (H-depleted)
nO Number of Oxygen atoms
nF Number of Fluorine atoms
nHM Number of Heavy atoms

Table 2. The values of the constants of Eq. (2) and their statistical interpretations.

Regression Errors Regression Confidence Standard Regression

ID Variable
Coefficient Coefficient Intervals (0.95) Coefficient
0 intercept 50.16088267 4.075696 0 0
1 nSK -80.52012489 1.175295 -1.081325919 3.60196
2 SCBO 53.64545627 0.9837223 0.858696667 3.593514
3 nO -169.2188895 1.424115 -0.552855974 1.061814
4 nF -174.7547718 1.178939 -0.680669749 1.047946
5 nHM -266.5765885 6.857063 -0.171389892 1.006101

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 K X of X-block of the predictor variables with the
multivariate correlation index K XY obtained by the augmented X-block matrix by adding the column
of the response variable. This rule says that if K XY is greater than K X , the model is predictive [13].
Obtained values of these two indexes in our problem are K X = 31.62 and K XY = 40.81 , as a result,
with respect to this quick rule, obtained model is predictive ( K XY > K X ).
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 ( Q 2 ) was 0.9826. The difference between R 2 and Q 2 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
2
times. After 5000 times repetition of this technique, the parameter QBoot was 0.9823. As can be found,
Int. J. Mol. Sci. 2007, 8 411

2
the difference between the QBoot , Q 2 ,and R 2 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)
2
was checked. The squared cross validated coefficient for the test ( Qext ) set is 0.9894, which the
promising difference between this value and the value of Q 2 shows the prediction power of the Eq. (2).
The calculated and DIPPR 801 values of ∆H f for training set are presented in the Table-3. Also,
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the predicted and DIPPR 801 values of ∆H f for test set are presented in Table 4. The comparison
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between the results of Eq.(2) and the DIPPR 801 values for training set and test set are shown in the
Figure 1.

1000

0
Training set

Prediction set
−1000
∆Hof calculated from Eq.(2) [KJ/mol]

−2000

−3000

−4000

−5000

−6000

−7000

−8000
−8000 −7000 −6000 −5000 −4000 −3000 −2000 −1000 0 1000
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∆Hf from DIPPR 801 [KJ/mol]

Figure 1. Comparison between the results of Eq. (2) for training set and predicted values
for training set.

3. Discussion

In the formation of a molecule from its constituent elements, ∆H f , is the difference between the
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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 ∆H f of that molecule. Of them, the number of atoms and number of the bonds and order
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Int. J. Mol. Sci. 2007, 8 412

of the bonds and number of non-organic elements (heavy atoms) in a molecule directly affect on the
value of ∆H f .
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Increase in the values of number of atoms in the H-depleted chemical structure of molecule
decreases ∆H f of a molecule. Increase in the order of bonds in a molecule increases ∆H f . Also the
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number of atoms which are commonly existed in all molecules such as oxygen and fluorine atoms, and
even heavy atoms affect ∆H f of a molecule. Increase in the number of these atoms in a molecule,
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decreases ∆H f of that molecule.

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Table 3. The obtained results from Eq. (2) for training set.

ID Name ∆Hfo(kJ/mol) Res

DIPPR 801 Calculated from Eq. (2)
1 n-BUTANE -125.79 -110.98 14.81
2 n-HEXANE -198.66 -164.73 33.93
3 3-METHYLPENTANE -202.38 -164.73 37.65
4 n-HEPTANE -224.05 -191.61 32.44
5 3-METHYLHEXANE -226.44 -191.61 34.83
6 3-ETHYLPENTANE -224.56 -191.61 32.95
7 2,2-DIMETHYLPENTANE -238.28 -191.61 46.67
8 2,3-DIMETHYLPENTANE -233.09 -191.61 41.48
9 2,4-DIMETHYLPENTANE -234.6 -191.61 42.99
10 3,3-DIMETHYLPENTANE -234.18 -191.61 42.57
11 2,2,3-TRIMETHYLBUTANE -236.52 -191.61 44.91
12 2-METHYLHEPTANE -255.01 -218.48 36.53
13 4-METHYLHEPTANE -251.63 -218.48 33.15
14 3-ETHYLHEXANE -250.41 -218.48 31.93
15 2,2-DIMETHYLHEXANE -261.88 -218.48 43.4
16 2,3-DIMETHYLHEXANE -252.59 -218.48 34.11
17 2,4-DIMETHYLHEXANE -257.02 -218.48 38.54
18 3,3-DIMETHYLHEXANE -257.53 -218.48 39.05
19 2-METHYL-3-ETHYLPENTANE -249.58 -218.48 31.1
20 2,2,3-TRIMETHYLPENTANE -256.9 -218.48 38.42
21 2,2,4-TRIMETHYLPENTANE -259.16 -218.48 40.68
22 2,3,3-TRIMETHYLPENTANE -253.51 -218.48 35.03
23 2,3,4-TRIMETHYLPENTANE -255.01 -218.48 36.53
24 n-NONANE -274.68 -245.36 29.32
25 3,3,5-TRIMETHYLHEPTANE -304.76 -272.23 32.53
26 2,4,4-TRIMETHYLHEXANE -280.2 -245.36 34.84
27 3,3-DIETHYLPENTANE -275.39 -245.36 30.03
28 2,2,3,3-TETRAMETHYLPENTANE -278.28 -245.36 32.92
29 2,2,4,4-TETRAMETHYLPENTANE -279.99 -245.36 34.63
30 SQUALANE -806.3 -809.72 -3.42
31 n-DECANE -300.62 -272.23 28.39
32 2,2,5,5-TETRAMETHYLHEXANE -323.51 -272.23 51.28
33 n-UNDECANE -326.6 -299.11 27.49
34 n-DODECANE -352.13 -325.98 26.15
35 n-TRIDECANE -377.69 -352.86 24.83
36 n-TETRADECANE -403.25 -379.73 23.52
37 n-PENTADECANE -428.82 -406.6 22.22
38 n-HEXADECANE -456.14 -433.48 22.66
39 n-OCTADECANE -567.14 -487.23 79.91
40 n-NONADECANE -596.21 -514.1 82.11
41 n-HENEICOSANE -653.45 -567.85 85.6
42 n-DOCOSANE -682.07 -594.73 87.34
43 n-TRICOSANE -710.69 -621.6 89.09
Int. J. Mol. Sci. 2007, 8 413

44 n-PENTACOSANE -767.93 -675.35 92.58

45 n-HEXACOSANE -796.55 -702.23 94.32
46 n-HEPTACOSANE -825.17 -729.1 96.07
47 n-OCTACOSANE -853.79 -755.98 97.81
48 n-NONACOSANE -882.41 -782.85 99.56
49 2-METHYLNONANE -311.9 -272.23 39.67
50 5-METHYLNONANE -310 -272.23 37.77
51 2,2,4,4,6,8,8-HEPTAMETHYLNONANE -476.87 -433.48 43.39
52 3-METHYLOCTANE -278.53 -245.36 33.17
53 4-METHYLOCTANE -279.6 -245.36 34.24
54 3-ETHYLHEPTANE -275.48 -245.36 30.12
55 2,2-DIMETHYLHEPTANE -288.2 -245.36 42.84
56 3-METHYLUNDECANE -355.2 -325.98 29.22
57 ETHYLCYCLOPENTANE -163.43 -137.96 25.47
58 cis-1,2-DIMETHYLCYCLOPENTANE -165.27 -137.96 27.31
59 trans-1,3-DIMETHYLCYCLOPENTANE -168.07 -137.96 30.11
60 n-PROPYLCYCLOPENTANE -189.07 -164.84 24.23
61 1-METHYL-1-ETHYLCYCLOPENTANE -193.8 -164.84 28.96
62 n-PROPYLCYCLOHEXANE -237.4 -191.71 45.69
63 ISOPROPYLCYCLOHEXANE -239.45 -191.71 47.74
64 1,1-DIETHYLCYCLOHEXANE -277.11 -218.59 58.52
65 n-DECYLCYCLOHEXANE -417 -379.83 37.17
66 CYCLOHEPTANE -156.61 -137.96 18.65
67 CYCLOOCTANE -167.74 -164.84 2.9
68 trans-1,4-DIETHYLCYCLOHEXANE -266.1 -218.59 47.51
69 2,6-DIMETHYLHEPTANE -286.12 -245.36 40.76
70 2,2-DIMETHYL-3-ETHYLPENTANE -272.7 -245.36 27.34
71 2,4-DIMETHYL-3-ETHYLPENTANE -269.7 -245.36 24.34
72 1-TRIACONTENE -761.6 -756.08 5.52
73 2-METHYL-1-BUTENE -60.96 -84.21 -23.25
74 cis-2-HEXENE -80.11 -111.09 -30.98
75 trans-2-HEXENE -85.52 -111.09 -25.57
76 cis-3-HEXENE -78.95 -111.09 -32.14
77 2-METHYL-1-PENTENE -89.96 -111.09 -21.13
78 3-METHYL-1-PENTENE -78.16 -111.09 -32.93
79 4-METHYL-1-PENTENE -80.04 -111.09 -31.05
80 2-METHYL-2-PENTENE -98.53 -111.09 -12.56
81 4-METHYL-1-HEXENE -101.5 -137.96 -36.46
82 4-METHYL-cis-2-PENTENE -87.03 -111.09 -24.06
83 4-METHYL-trans-2-PENTENE -91.55 -111.09 -19.54
84 2-ETHYL-1-BUTENE -87.11 -111.09 -23.98
85 2,3-DIMETHYL-1-BUTENE -95.6 -111.09 -15.49
86 3,3-DIMETHYL-1-BUTENE -88.28 -111.09 -22.81
87 2-ETHYL-1-PENTENE -109.9 -137.96 -28.06
88 1-HEPTENE -98.37 -137.96 -39.59
89 cis-2-HEPTENE -105.1 -137.96 -32.86
90 trans-2-HEPTENE -109.5 -137.96 -28.46
91 trans-3-HEPTENE -109.33 -137.96 -28.63
92 2-METHYL-1-HEXENE -112.6 -137.96 -25.36
93 3-ETHYL-1-PENTENE -98.49 -137.96 -39.47
94 3-METHYL-1-HEXENE -101.1 -137.96 -36.86
95 3-ETHYL-1-HEXENE -124.6 -164.84 -40.24
96 2,3,3-TRIMETHYL-1-BUTENE -117.7 -137.96 -20.26
97 cis-3-HEPTENE -104.35 -137.96 -33.61
98 1-OCTENE -122 -164.84 -42.84
99 2,4,4-TRIMETHYL-1-PENTENE -146.15 -164.84 -18.69
100 2-ETHYL-1-HEXENE -136.42 -164.84 -28.42
101 1-NONENE -148.8 -191.71 -42.91
102 1-UNDECENE -200.8 -245.46 -44.66
103 1-DODECENE -226.2 -272.34 -46.14
104 1-TRIDECENE -253.5 -299.21 -45.71
105 1-TETRADECENE -280.3 -326.08 -45.78
106 1-HEXADECENE -329.24 -379.83 -50.59
Int. J. Mol. Sci. 2007, 8 414

107 1-OCTADECENE -374.77 -433.58 -58.81

108 6-METHYL-1-HEPTENE -129.5 -164.84 -35.34
109 CYCLOHEXENE -38.2 -57.44 -19.24
110 trans-2-EICOSENE -446.6 -487.33 -40.73
111 trans-2-PENTADECENE -319.5 -352.96 -33.46
112 cis-2-OCTENE -129.4 -164.84 -35.44
113 trans-3-OCTENE -134.38 -164.84 -30.46
114 cis-4-OCTENE -128.49 -164.84 -36.35
115 trans-4-OCTENE -134.61 -164.84 -30.23
116 cis-3-OCTENE -129.14 -164.84 -35.7
117 1-EICOSENE -459.21 -487.33 -28.12
118 1-METHYLCYCLOPENTENE -36.44 -57.44 -21
119 2,3-DIMETHYL-1-HEXENE -136 -164.84 -28.84
120 1,4-DI-tert-BUTYLBENZENE -188.9 -165.15 23.75
121 alpha-TOCOPHEROL -873.4 -879.94 -6.54
122 1,2,3-TRIETHYLBENZENE -130.32 -111.4 18.92
123 n-HEPTYLBENZENE -140.6 -138.27 2.33
124 1,2,3,5-TETRAETHYLBENZENE -196.36 -165.15 31.21
125 n-DECYLBENZENE -217.5 -218.9 -1.4
126 PENTAETHYLBENZENE -258.1 -218.9 39.2
127 m-TERPHENYL 165.58 156.52 -9.06
128 n-PENTYLBENZENE -89.5 -84.52 4.98
129 n-HEXYLBENZENE -115 -111.4 3.6
130 n-OCTYLBENZENE -166.1 -165.15 0.95
131 n-NONYLBENZENE -190.4 -192.02 -1.62
132 n-UNDECYLBENZENE -241.18 -245.77 -4.59
133 n-TRIDECYLBENZENE -288.73 -299.52 -10.79
134 n-TETRADECYLBENZENE -311.49 -326.4 -14.91
135 n-DODECYLBENZENE -264.79 -272.65 -7.86
136 2,3-DIMETHYL-2,3-DIPHENYLBUTANE -59.68 -58.06 1.62
137 1,1,2-TRIPHENYLETHANE 130.2 102.77 -27.43
138 TETRAPHENYLMETHANE 247.1 182.98 -64.12
139 1,1,2,2-TETRAPHENYLETHANE 216 156.1 -59.9
140 1-(4-ETHYLPHENYL)-2-PHENYLETHANE 12.03 -4.32 -16.35
141 STYRENE 103.47 49.75 -53.72
142 1-n-NONYLNAPHTHALENE -132.57 -111.76 20.81
143 1-n-DECYLNAPHTHALENE -156.26 -138.64 17.62
144 1-n-HEXYL-1,2,3,4-TETRAHYDRONAPHTHALENE -179.33 -165.25 14.08
145 1-PHENYLINDENE 148.61 129.85 -18.76
146 TRIPHENYLETHYLENE 233.38 156.41 -76.97
147 TETRAPHENYLETHYLENE 311.5 209.75 -101.75
148 trans-STILBENE 136.9 103.08 -33.82
149 ACENAPHTHALENE 186.6 183.65 -2.95
150 sec-BUTYLCYCLOHEXANE -263.7 -218.59 45.11
151 PIMARIC ACID -634.1 -611.29 22.81
152 ISOPIMARIC ACID -670.4 -611.29 59.11
153 SULFUR DIOXIDE -296.84 -315.26 -18.42
154 SULFUR TRIOXIDE -441.04 -457.7 -16.66
155 ACETALDEHYDE -166.4 -199.68 -33.28
156 PROPANAL -215.3 -226.56 -11.26
157 1,2,3,6-TETRAHYDROBENZALDEHYDE -162.1 -226.76 -64.66
158 BUTANAL -239.2 -253.43 -14.23
159 HEPTANAL -311.5 -334.06 -22.56
160 HEXANAL -291.83 -307.18 -15.35
161 OCTANAL -342.7 -360.93 -18.23
162 NONANAL -367.93 -387.8 -19.87
163 2-ETHYLHEXANAL -348.5 -360.93 -12.43
164 2-METHYLHEXANAL -317.47 -334.06 -16.59
165 2-METHYL-2-PENTENAL -201.8 -253.54 -51.74
166 2-ETHYL-2-HEXENAL -244.6 -307.28 -62.68
167 DECANAL -393.84 -414.68 -20.84
168 UNDECANAL -419.06 -441.55 -22.49
169 DODECANAL -445.25 -468.43 -23.18
Int. J. Mol. Sci. 2007, 8 415

170 2-METHYLBUTYRALDEHYDE -271.5 -280.31 -8.81

171 3-METHYLBUTYRALDEHYDE -276.5 -280.31 -3.81
172 cis-CROTONALDEHYDE -137.7 -199.79 -62.09
173 trans-CROTONALDEHYDE -138.7 -199.79 -61.09
174 o-TOLUALDEHYDE -113.18 -146.35 -33.17
175 p-HYDROXYBENZALDEHYDE -310.82 -315.57 -4.75
176 TEREPHTHALDEHYDE -243.43 -288.8 -45.37
177 2-METHYL OCTANAL -370.2 -387.8 -17.6
178 METHYL ETHYL KETONE -273.3 -253.43 19.87
179 METHYL ISOBUTYL KETONE -328.4 -307.18 21.22
180 3-METHYL-2-PENTANONE -323.8 -307.18 16.62
181 3-HEPTANONE -348.6 -334.06 14.54
182 4-HEPTANONE -346.2 -334.06 12.14
183 3-HEXANONE -320.2 -307.18 13.02
184 2-HEXANONE -322.01 -307.18 14.83
185 MESITYL OXIDE -238.14 -253.54 -15.4
186 3,3-DIMETHYL-2-BUTANONE -328.6 -307.18 21.42
187 DIISOBUTYL KETONE -408.5 -387.8 20.7
188 DIISOPROPYL KETONE -352.92 -334.06 18.86
189 2-PYRROLIDONE -266.04 -226.66 39.38
190 N-METHYL-2-PYRROLIDONE -262.2 -253.54 8.66
191 ETHYL ISOAMYL KETONE -374.4 -360.93 13.47
192 5-NONANONE -398.24 -387.8 10.44
193 2-NONANONE -396.8 -387.8 9
194 ACETYLACETONE -423.8 -422.75 1.05
195 CYCLOPENTANONE -235.7 -226.66 9.04
196 CYCLOHEXANONE -271.2 -253.54 17.66
197 2-OCTANONE -372.7 -360.93 11.77
198 BENZOPHENONE -37.3 -66.14 -28.84
199 ACETOPHENONE -142.5 -146.35 -3.85
200 beta-PROPIOLACTONE -329.9 -369 -39.1
201 2-CYCLOHEXYL CYCLOHEXANONE -390.98 -361.14 29.84
202 METHANOL -239.1 -226.45 12.65
203 ETHANOL -276.98 -253.33 23.65
204 1-PROPANOL -302.6 -280.2 22.4
205 ISOPROPANOL -318.1 -280.2 37.9
206 1-BUTANOL -327.2 -307.08 20.12
207 2-BUTANOL -342.6 -307.08 35.52
208 2-METHYL-2-PROPANOL -365.9 -307.08 58.82
209 1-PENTANOL -351.6 -333.95 17.65
210 2-PENTANOL -365.2 -333.95 31.25
211 2-METHYL-1-BUTANOL -356.6 -333.95 22.65
212 2,2-DIMETHYL-1-PROPANOL -382.01 -333.95 48.06
213 1-HEXANOL -377.5 -360.83 16.67
214 2-HEXANOL -392 -360.83 31.17
215 3-METHYL-1-PENTANOL -380.9 -360.83 20.07
216 3-PENTANOL -370.33 -333.95 36.38
217 2-ETHYL-1-HEXANOL -432.8 -414.58 18.22
218 2-METHYL-1-HEXANOL -404.5 -387.7 16.8
219 3-METHYL-1-BUTANOL -356.4 -333.95 22.45
220 1-HEPTANOL -403.3 -387.7 15.6
221 1-NONANOL -453.6 -441.45 12.15
222 1-DECANOL -478.1 -468.32 9.78
223 1-UNDECANOL -504.8 -495.2 9.6
224 8-METHYL-1-NONANOL -483.13 -468.32 14.81
225 1-DODECANOL -528.5 -522.07 6.43
226 1-TRIDECANOL -599.4 -548.95 50.45
227 1-TETRADECANOL -628.18 -575.82 52.36
228 1-PENTADECANOL -658.2 -602.7 55.5
229 1-HEPTADECANOL -722.85 -656.45 66.4
230 2-ETHYL-1-BUTANOL -382.41 -360.83 21.58
231 1-METHYLCYCLOHEXANOL -388.17 -334.06 54.11
232 cis-2-METHYLCYCLOHEXANOL -390.2 -334.06 56.14
Int. J. Mol. Sci. 2007, 8 416

233 cis-3-METHYLCYCLOHEXANOL -416.1 -334.06 82.04

234 trans-3-METHYLCYCLOHEXANOL -394.4 -334.06 60.34
235 cis-4-METHYLCYCLOHEXANOL -413.2 -334.06 79.14
236 trans-4-METHYLCYCLOHEXANOL -433.3 -334.06 99.24
237 AGATHADIOL -685.7 -718.58 -32.88
238 alpha-TERPINEOL -316.7 -361.03 -44.33
239 2-BUTYL-NONAN-1-OL -540.1 -548.95 -8.85
240 TETRAHYDROFURFURYL ALCOHOL -435.7 -476.4 -40.7
241 2-PHENYL-2-PROPANOL -244.43 -226.87 17.56
242 2-BUTYL-OCTAN-1-OL -512.2 -522.07 -9.87
243 2,6-XYLENOL -237.4 -199.99 37.41
244 BENZYL ALCOHOL -160.71 -173.12 -12.41
245 m-CRESOL -194 -173.12 20.88
246 o-ETHYLPHENOL -208.82 -199.99 8.83
247 p-HYDROQUINONE -371.1 -342.34 28.76
248 p-ETHYLPHENOL -224.39 -199.99 24.4
249 p-tert-BUTYLPHENOL -276.66 -253.74 22.92
250 BISPHENOL A -368.5 -369.63 -1.13
251 NONYLPHENOL -387.33 -388.12 -0.79
252 ETHYLENE GLYCOL -460 -449.42 10.58
253 DIETHYLENE GLYCOL -628.5 -699.26 -70.76
254 TETRAETHYLENE GLYCOL -981.7 -1198.95 -217.25
255 1,2-PROPYLENE GLYCOL -499.99 -476.3 23.69
256 1,3-PROPYLENE GLYCOL -480.8 -476.3 4.5
257 DIPROPYLENE GLYCOL -718.46 -753.01 -34.55
258 2-METHYL-1,3-PROPANEDIOL -505.9 -503.17 2.73
259 1,2-BUTANEDIOL -523.6 -503.17 20.43
260 1,3-BUTANEDIOL -501 -503.17 -2.17
261 HEXYLENE GLYCOL -602.92 -556.92 46
262 GLYCEROL -669.6 -672.39 -2.79
263 p-tert-BUTYLCATECHOL -474 -449.84 24.16
264 2,2,4-TRIMETHYL-1,3-PENTANEDIOL -497.18 -610.67 -113.49
265 2-METHYL-1,3-PENTANEDIOL -577.5 -556.92 20.58
266 2,3-BUTANEDIOL -541.5 -503.17 38.33
267 cis-2-BUTENE-1,4-DIOL -372.9 -449.52 -76.62
268 trans-2-BUTENE-1,4-DIOL -401.6 -449.52 -47.92
269 1,5-PENTANEDIOL -531.49 -530.05 1.44
270 1,6-HEXANEDIOL -583.86 -556.92 26.94
271 1,2-BENZENEDIOL -354.1 -342.34 11.76
272 1,3-BENZENEDIOL -368 -342.34 25.66
273 PENTAERYTHRITOL -920.6 -922.23 -1.63
274 TRIMETHYLOLPROPANE -751.61 -753.01 -1.4
275 1,2,3-BENZENETRIOL -551.1 -538.43 12.67
276 SORBITOL -1354.2 -1341.29 12.91
277 FORMIC ACID -425.5 -368.9 56.6
278 ACETIC ACID -484.5 -395.78 88.72
279 PROPIONIC ACID -508.5 -422.65 85.85
280 n-DECANOIC ACID -713.7 -610.77 102.93
281 OXALIC ACID -829.7 -734.32 95.38
282 n-BUTYRIC ACID -533.8 -449.52 84.28
283 n-PENTANOIC ACID -558.7 -476.4 82.3
284 n-NONANOIC ACID -661.8 -583.9 77.9
285 ISOBUTYRIC ACID -531 -449.52 81.48
286 ISOVALERIC ACID -561.6 -476.4 85.2
287 n-HEXANOIC ACID -583.8 -503.27 80.53
288 2-METHYLHEXANOIC ACID -613.9 -530.15 83.75
289 1,4-CYCLOHEXANEDICARBOXYLIC ACID -998.5 -841.92 156.58
290 n-OCTANOIC ACID -636.8 -557.02 79.78
291 n-UNDECANOIC ACID -735.9 -637.65 98.25
292 CYCLOPENTYLACETIC ACID -551.73 -476.5 75.23
293 DILACTIC ACID -1122.8 -1037.91 84.89
294 n-DODECANOIC ACID -774.6 -664.52 110.08
295 n-HEXADECANOIC ACID -891.5 -772.02 119.48
Int. J. Mol. Sci. 2007, 8 417

296 trans-CROTONIC ACID -446.23 -395.88 50.35

297 STEARIC ACID -948 -825.77 122.23
298 ACRYLIC ACID -383.88 -369 14.88
299 OLEIC ACID -802.49 -772.12 30.37
300 LINOLEIC ACID -674.04 -718.48 -44.44
301 SALICYLIC ACID -589.9 -511.66 78.24
302 ADIPIC ACID -994.3 -841.82 152.48
303 MALEIC ACID -789.4 -734.42 54.98
304 TEREPHTHALIC ACID -816.18 -680.98 135.2
305 ACETIC ANHYDRIDE -624.4 -591.97 32.43
306 PROPIONIC ANHYDRIDE -679.1 -645.72 33.38
307 BUTYRIC ANHYDRIDE -719.12 -699.47 19.65
308 PALUSTRIC ACID -852.4 -664.94 187.46
309 SUCCINIC ANHYDRIDE -607.8 -538.33 69.47
310 GLUTARIC ANHYDRIDE -618.5 -565.2 53.3
311 PHTHALIC ANHYDRIDE -460.1 -431.24 28.86
312 MALEIC ANHYDRIDE -469.8 -484.68 -14.88
313 TRIMELLITIC ANHYDRIDE -894.81 -796.66 98.15
314 METHYL FORMATE -386.1 -395.78 -9.68
315 n-PROPYL FORMATE -445.2 -449.52 -4.32
316 n-BUTYL FORMATE -469.2 -476.4 -7.2
317 ISOBUTYL FORMATE -475.87 -476.4 -0.53
318 n-PENTYL FORMATE -493.28 -503.27 -9.99
319 n-OCTYL FORMATE -566.45 -583.9 -17.45
320 n-NONYL FORMATE -588.93 -610.77 -21.84
321 n-DECYL FORMATE -613.73 -637.65 -23.92
322 VINYL FORMATE -293.36 -369 -75.64
323 ETHYL ACETATE -478.8 -449.52 29.28
324 n-PROPYL ACETATE -504.32 -476.4 27.92
325 n-BUTYL ACETATE -529.2 -503.27 25.93
326 ISOBUTYL ACETATE -536.06 -503.27 32.79
327 ISOPENTYL ACETATE -558.69 -530.15 28.54
328 ALLYL ACETATE -386.3 -422.75 -36.45
329 ISOPROPYL ACETATE -518.8 -476.4 42.4
330 sec-BUTYL ACETATE -544.04 -503.27 40.77
331 VINYL ACETATE -349.7 -395.88 -46.18
332 METHYL PROPIONATE -463.3 -449.52 13.78
333 ETHYL PROPIONATE -502.7 -476.4 26.3
334 n-PROPYL PROPIONATE -527.5 -503.27 24.23
335 n-BUTYL PROPIONATE -549.9 -530.15 19.75
336 VINYL PROPIONATE -385.46 -422.75 -37.29
337 ETHYL n-BUTYRATE -514.63 -503.27 11.36
338 n-PROPYL ISOBUTYRATE -564.5 -530.15 34.35
339 METHYL ACRYLATE -362.2 -395.88 -33.68
340 ETHYL ACRYLATE -379.59 -422.75 -43.16
341 n-PROPYL ACRYLATE -407.17 -449.63 -42.46
342 n-BUTYL NONANOATE -697.78 -691.4 6.38
343 n-BUTYL VALERATE -613.3 -583.9 29.4
344 ETHYL ISOVALERATE -570.9 -530.15 40.75
345 METHYL METHACRYLATE -399.13 -422.75 -23.62
346 ETHYL METHACRYLATE -421.34 -449.63 -28.29
347 n-PROPYL METHACRYLATE -446.7 -476.5 -29.8
348 DIOCTYL PHTHALATE -1084.1 -1110.98 -26.88
349 DIISOOCTYL PHTHALATE -1087.3 -1110.98 -23.68
1,2-BENZENEDICARBOXYLIC ACID, HEPTYL, NONYL
350 ESTER -1085 -1110.98 -25.98
351 n-PENTYL ACETATE -553 -530.15 22.85
352 2-ETHYLHEXYL ACETATE -627.99 -610.77 17.22
353 BENZYL ACETATE -368.8 -369.32 -0.52
354 ISOBUTYL ISOBUTYRATE -594.07 -557.02 37.05
355 ISOPENTYL ISOVALERATE -644.74 -610.77 33.97
356 METHYL OLEATE -734.5 -799 -64.5
357 n-HEXYL ACETATE -577.9 -557.02 20.88
Int. J. Mol. Sci. 2007, 8 418

358 n-BUTYL BENZOATE -429.06 -423.07 5.99

359 n-HEPTYL ACETATE -602.67 -583.9 18.77
360 n-OCTYL ACETATE -628.25 -610.77 17.48
361 n-DECYL ACETATE -679.25 -664.52 14.73
362 DIISODECYL PHTHALATE -1196.9 -1218.48 -21.58
363 METHYL SALICYLATE -531.79 -538.54 -6.75
364 DI-n-NONYL PHTHALATE -1134.8 -1164.73 -29.93
365 DI-n-PROPYL PHTHALATE -811.89 -842.23 -30.34
366 DIISOBUTYL PHTHALATE -890 -895.98 -5.98
367 DIMETHYL ISOPHTHALATE -730.9 -734.73 -3.83
368 DI-n-DECYL PHTHALATE -1197 -1218.48 -21.48
369 DI-n-UNDECYL PHTHALATE -1248 -1325.98 -77.98
370 DI-n-HEXYL PHTHALATE -987.8 -1003.48 -15.68
371 DIMETHYL TEREPHTHALATE -732.6 -734.73 -2.13
372 DI-n-OCTYL TEREPHTHALATE -1181.2 -1110.98 70.22
373 n-BUTYL STEARATE -978.16 -933.27 44.89
374 DIBUTYL SEBACATE -1156.7 -1164.31 -7.61
375 n-BUTYL n-BUTYRATE -575.39 -557.02 18.37
376 n-BUTYL METHACRYLATE -471.39 -503.38 -31.99
377 METHYL BENZOATE -343.5 -342.44 1.06
378 ETHYL BENZOATE -379.91 -369.32 10.59
379 DIETHYL CARBONATE -682.65 -672.49 10.16
380 DIETHYL OXALATE -806.28 -841.82 -35.54
381 DIETHYL MALONATE -838.02 -868.69 -30.67
382 ISOPROPYL MYRISTATE -820.33 -798.9 21.43
383 TRI-n-HEPTYL TRIMELLITATE -1697 -1610.77 86.23
1,2-BENZENE DICARBOXYLIC ACID, HEPTYL,
384 UNDECYL ESTER -1137 -1164.73 -27.73
385 DIMETHYL ETHER -184.1 -253.33 -69.23
386 DIETHYL ETHER -279.4 -307.08 -27.68
387 DIISOPROPYL ETHER -351.5 -360.83 -9.33
388 DI-n-BUTYL ETHER -377.9 -414.58 -36.68
389 METHYL tert-BUTYL ETHER -313.6 -333.95 -20.35
390 DI-sec-BUTYL ETHER -401.5 -414.58 -13.08
391 METHYL ETHYL ETHER -216.4 -280.2 -63.8
392 METHYL n-PROPYL ETHER -265.89 -307.08 -41.19
393 ISOPROPYL BUTYL ETHER -365.64 -387.7 -22.06
394 METHYL ISOBUTYL ETHER -296.13 -333.95 -37.82
395 DI-n-HEXYL ETHER -481.96 -522.07 -40.11
396 METHYL n-BUTYL ETHER -290.6 -333.95 -43.35
397 ETHYL PROPYL ETHER -303.59 -333.95 -30.36
398 1,4-DIOXANE -355.1 -449.52 -94.42
399 TRIOXANE -522.5 -618.74 -96.24
400 DI-tert-BUTYL ETHER -399.61 -414.58 -14.97
401 DI-n-OCTYL ETHER -582.75 -629.57 -46.82
402 DI-n-PENTYL ETHER -425.12 -468.32 -43.2
403 METHYL sec-BUTYL ETHER -305.24 -333.95 -28.71
404 tert-BUTYL ETHYL ETHER -346.83 -360.83 -14
405 METHYL n-PENTYL ETHER -315.1 -360.83 -45.73
406 ETHYL tert-PENTYL ETHER -369.07 -387.7 -18.63
407 METHYLAL -378.2 -476.3 -98.1
408 ACETAL -491.41 -556.92 -65.51
409 ETHYL ISOBUTYL ETHER -333.5 -360.83 -27.33
410 DI-n-PROPYL ETHER -328.82 -360.83 -32.01
411 n-BUTYL ETHYL ETHER -328.7 -360.83 -32.13
412 DIETHYLENE GLYCOL DI-n-BUTYL ETHER -723.58 -914.26 -190.68
413 BENZYL ETHYL ETHER -165.78 -226.87 -61.09
414 PHENETOLE -152.6 -199.99 -47.39
415 1-METHYL-3-(METHYLETHOXY)BENZENE -221.6 -253.74 -32.14
416 1,1-DIMETHOXYETHANE -420.1 -503.17 -83.07
417 2,5-DIHYDROFURAN -141.36 -199.79 -58.43
418 TETRAHYDROFURAN -216.19 -253.43 -37.24
419 1-tert-BUTOXY-2-[2-(tert-BUTOXY)PROPOXY]PROPANE -810.3 -968.01 -157.71
Int. J. Mol. Sci. 2007, 8 419

420 1,2-DIMETHOXYPROPANE -422.3 -530.05 -107.75

421 sec-BUTYL-tert-BUTYL ETHER -417.5 -414.58 2.92
422 ISOBUTYL-tert-BUTYL ETHER -407 -414.58 -7.58
423 1,4-DICHLORO-trans-2-BUTENE -112.53 -111.09 1.44
424 HEXACHLOROETHANE -202.8 -218.48 -15.68
425 1,1,1,2-TETRACHLOROETHANE -191 -164.73 26.27
426 1,1,2,2-TETRACHLOROETHANE -194.6 -164.73 29.87
427 HEXACHLOROCYCLOPENTADIENE -159.78 -138.17 21.61
428 PENTACHLOROETHANE -187.6 -191.61 -4.01
429 3,4-DICHLORO-1-BUTENE -106.91 -111.09 -4.18
430 DICHLORODIFLUOROMETHANE -491.62 -487.37 4.25
431 TRICHLOROFLUOROMETHANE -288.7 -312.61 -23.91
432 CHLOROTRIFLUOROMETHANE -707.93 -662.12 45.81
433 2-CHLORO-1,1,1-TRIFLUOROETHANE -741.8 -689 52.8
434 1,2-DICHLOROTETRAFLUOROETHANE -916.3 -917.5 -1.2
435 1,2-DIBROMOTETRAFLUOROETHANE -807.1 -917.5 -110.4
436 METHYL FLUORIDE -234.3 -231.99 2.31
437 DIFLUOROMETHANE -452.3 -433.62 18.68
438 TRIFLUOROMETHANE -697.05 -635.25 61.8
439 CARBON TETRAFLUORIDE -933.15 -836.88 96.27
440 ETHYL FLUORIDE -264.4 -258.86 5.54
441 1,1,1-TRIFLUOROETHANE -736.4 -662.12 74.28
442 DECAFLUOROBUTANE -2149.7 -2127.28 22.42
443 PERFLUORO-n-DECANE -4710 -4708.08 1.92
444 1,1-DIFLUOROETHYLENE -328.96 -406.85 -77.89
445 TETRAFLUOROETHYLENE -658.56 -810.11 -151.55
446 BROMODIFLUOROMETHANE -424.9 -460.49 -35.59
447 1,1-DIFLUOROETHANE -497 -460.49 36.51
448 1-BROMOPROPANE -121.8 -110.98 10.82
449 1-BROMOBUTANE -143.8 -137.86 5.94
450 1-BROMOHEPTANE -218.4 -218.48 -0.08
451 1,2-DIBROMOETHANE -79.2 -110.98 -31.78
452 1,1,1-TRICHLOROTRIFLUOROETHANE -822 -742.75 79.25
453 ISOPROPYL IODIDE -74.8 -110.98 -36.18
454 2,2-DICHLORO-1,1,1-TRIFLUOROETHANE -770.3 -715.87 54.43
455 HEXAFLUOROPROPYLENE -1079 -1240.24 -161.24
456 2-METHYL-2-AMINOBUTANE -171.4 -164.73 6.67
457 DI-n-PROPYLAMINE -156.11 -191.61 -35.5
458 DIETHYLAMINE -103.7 -137.86 -34.16
459 n-PROPYLAMINE -101.47 -110.98 -9.51
460 n-PENTYLAMINE -152.62 -164.73 -12.11
461 ISOBUTYLAMINE -132.6 -137.86 -5.26
462 DIISOBUTYLAMINE -218.5 -245.36 -26.86
463 PYRROLE 63.11 49.9 -13.21
464 METHYL DIETHANOLAMINE -473.77 -556.92 -83.15
465 DIETHANOLAMINE -493.8 -530.05 -36.25
466 TRIETHANOLAMINE -667.35 -779.89 -112.54
467 sec-BUTYLAMINE -137.49 -137.86 -0.37
468 tert-BUTYLAMINE -150.6 -137.86 12.74
469 CYCLOHEXYLAMINE -147.7 -137.96 9.74
470 HEXAMETHYLENEDIAMINE -192.42 -218.48 -26.06
471 DIISOPROPYLAMINE -178.5 -191.61 -13.11
472 DI-n-BUTYLAMINE -206 -245.36 -39.36
473 PIPERIDINE -86.4 -111.09 -24.69
474 QUINOLINE 141.22 130.11 -11.11
475 FORMANILIDE -151.46 -146.35 5.11
476 1,2-PROPANEDIAMINE -97.8 -137.86 -40.06
477 N-METHYLPYRROLE 62.38 23.03 -39.35
478 DIPHENYLAMINE 130 76.31 -53.69
479 HYDRACRYLONITRILE -161.2 -199.79 -38.59
480 HYDROGEN CYANIDE 108.19 50.06 -58.13
481 ACETONITRILE 40.56 23.18 -17.38
482 METHACRYLONITRILE 64.78 23.08 -41.7
Int. J. Mol. Sci. 2007, 8 420

483 VALERONITRILE -33.1 -57.44 -24.34

484 BENZONITRILE 163.18 103.39 -59.79
485 PYRIDINE 100.2 49.85 -50.35
486 HEXAMETHYLENEIMINE -103.82 -137.96 -34.14
487 2-METHYLPYRIDINE 56.7 22.97 -33.73
488 tert-BUTYL MERCAPTAN -140.5 -137.86 2.64
489 ISOBUTYL MERCAPTAN -132 -137.86 -5.86
490 sec-BUTYL MERCAPTAN -131 -137.86 -6.86
491 n-HEXYL MERCAPTAN -175.7 -191.61 -15.91
492 n-NONYL MERCAPTAN -248.66 -272.23 -23.57
493 n-OCTYL MERCAPTAN -224.47 -245.36 -20.89
494 CYCLOHEXYL MERCAPTAN -140.7 -137.96 2.74
495 METHYL ETHYL SULFIDE -91.6 -110.98 -19.38
496 METHYL n-PROPYL SULFIDE -118.5 -137.86 -19.36
497 METHYL t-BUTYL SULFIDE -157.1 -164.73 -7.63
498 DI-n-PROPYL SULFIDE -169.9 -191.61 -21.71
499 ETHYL n-OCTYL SULFIDE -273.3 -299.11 -25.81
500 DIMETHYL SULFIDE -65.4 -84.11 -18.71
501 THIOPHENE 80.2 49.9 -30.3
502 DIETHYL DISULFIDE -120.1 -164.73 -44.63
503 UNDECYL MERCAPTAN -302.87 -325.98 -23.11
504 n-DECYL MERCAPTAN -276.5 -299.11 -22.61
505 n-PENTYL MERCAPTAN -149.69 -164.73 -15.04
506 DICYCLOHEXYL SULFIDE -241.8 -245.56 -3.76
507 THIAINDAN 59.26 22.87 -36.39
508 n-DODECYL MERCAPTAN -327.18 -352.86 -25.68
509 tert-OCTYL MERCAPTAN -245.23 -245.36 -0.13
510 n-HEPTYL MERCAPTAN -200.5 -218.48 -17.98
511 n-BUTYL MERCAPTAN -124.7 -137.86 -13.16
512 TETRAHYDROTHIOPHENE -72.9 -84.21 -11.31
513 DIMETHYL SULFOXIDE -204.2 -226.56 -22.36
514 3-METHYL SULFOLANE -488 -395.98 92.02
515 DI-n-BUTYL SULFONE -609.86 -530.25 79.61
516 ACETYL CHLORIDE -272.8 -226.56 46.24
517 CHLOROACETIC ACID -510.5 -422.65 87.85
518 CHLOROACETYL CHLORIDE -283.7 -253.43 30.27
519 TRICHLOROACETYL CHLORIDE -280.8 -307.18 -26.38
520 BENZOYL CHLORIDE -158 -146.35 11.65
521 p-CHLOROBENZOTRIFLUORIDE -663.63 -608.79 54.84
522 2,4-DICHLOROBENZOTRIFLUORIDE -702.75 -635.66 67.09
523 FLUOROBENZENE -150.6 -151.78 -1.18
524 3-CHLORO-1,2-PROPANEDIOL -525.3 -503.17 22.13
525 1,3-DICHLORO-2-PROPANOL -385.3 -333.95 51.35
526 2,3-DICHLORO-1-PROPANOL -381.5 -333.95 47.55
527 DI(2-CHLOROETHYL)ETHER -356.2 -360.83 -4.63
528 3-(METHYLMERCAPTO)PROPANAL -211.1 -280.31 -69.21
529 TRIFLUOROACETIC ACID -1069.9 -1000.66 69.24
530 GLYCINE -528.1 -422.65 105.45
531 4-METHOXYPHENYLACETIC ACID -578.4 -565.41 12.99
532 N,N-DIMETHYLFORMAMIDE -239.2 -253.43 -14.23
533 2-METHACRYLAMIDE -269.68 -226.66 43.02
534 ACRYLAMIDE -212.08 -199.79 12.29
535 epsilon-CAPROLACTAM -328.5 -280.41 48.09
536 HEXAMETHYL PHOSPHORAMIDE -533.9 -414.68 119.22
537 ACETALDOL -433.62 -449.52 -15.9
538 FURFURAL -201.6 -288.64 -87.04
539 CARBONYL SULFIDE -142 -146.04 -4.04
540 PHOSGENE -218.9 -226.56 -7.66
541 ACETOMETHOXANE -873.7 -895.57 -21.87
542 ETHYLENE GLYCOL DIACRYLATE -662.81 -788.27 -125.46
PROPYLENE GLYCOL MONOMETHYL ETHER
543 ACETATE -663.23 -699.37 -36.14
DIPROPYLENE GLYCOL MONOMETHYL ETHER
544 ACETATE -878.99 -976.09 -97.1
Int. J. Mol. Sci. 2007, 8 421

545 SULFURIC ACID -813.99 -707.44 106.55

546 SULFUR HEXAFLUORIDE -1220.5 -1240.14 -19.64
547 SULFURYL CHLORIDE -394.1 -369 25.1
548 THIONYL CHLORIDE -245.6 -226.56 19.04
549 HEXAMETHYLCYCLOTRISILOXANE -1622 -1579.72 42.28
550 DODECAMETHYLPENTASILOXANE -2621 -2577.61 43.39
551 METHYL VINYL DICHLOROSILANE -380.8 -377.66 3.14
552 [3-(MERCAPTO)PROPYL]TRIETHOXYSILANE -1054 -1153.96 -99.96
553 3-(TRIMETHOXYSILYL)-1-PROPANETHIOL -933.1 -1073.34 -140.24
554 OCTAMETHYLCYCLOTETRASILOXANE -2195 -2123.02 71.98
555 GLUTARALDEHYDE -365.87 -422.75 -56.88
556 n-TRIACONTANE -911.03 -809.72 101.31
557 n-DOTRIACONTANE -969.93 -863.47 106.46
558 3-OCTANONE -371.8 -360.93 10.87
559 4-OCTANONE -373.1 -360.93 12.17
560 n-HEXATRIACONTANE -1082.8 -970.97 111.83
561 2-CYCLOHEXENE-1-ONE -170.9 -199.89 -28.99
562 2,3-DIMETHYLOCTANE -304.31 -272.23 32.08
563 2,4-DIMETHYLOCTANE -307.95 -272.23 35.72
564 2,5-DIMETHYLOCTANE -308.42 -272.23 36.19
565 2,6-DIMETHYLOCTANE -307.95 -272.23 35.72
566 m-ETHYLPHENOL -214.3 -199.99 14.31
567 2-PHENYLETHANOL -181.61 -199.99 -18.38
568 2,6-DIMETHYL-4-HEPTANOL -469.54 -441.45 28.09
569 1-PHENYL-1-PROPANOL -219.78 -226.87 -7.09
570 3-PHENYL-1-PROPANOL -217.9 -226.87 -8.97
571 beta-CHOLESTEROL -726.92 -656.97 69.95
572 alpha-METHYLBENZYL ALCOHOL -197.43 -199.99 -2.56
573 o-TOLUALCOHOL -206.7 -199.99 6.71
574 m-TOLUALCOHOL -197.3 -199.99 -2.69
575 p-tert-OCTYLPHENOL -392.44 -361.24 31.2
576 p-tert-AMYLPHENOL -300.85 -280.62 20.23
577 p-CUMYLPHENOL -172.25 -173.53 -1.28
578 2,4-PENTANEDIOL -556.35 -530.05 26.3
579 3-METHYL-trans-2-PENTENE -94.56 -111.09 -16.53
580 5-METHYL-1-HEXENE -100 -137.96 -37.96
581 DECAN-1,10-DIOL -699.71 -664.42 35.29
582 1,4-CYCLOHEXANEDIMETHANOL -584.6 -557.02 27.58
583 2-METHYL-1-OCTENE -165.1 -191.71 -26.61
584 2-METHYL-1-HEPTENE -134.18 -164.84 -30.66
585 TRIMELLITIC ACID -1179.2 -1046.4 132.8
586 TRILACTIC ACID -1547 -1457.08 89.92
587 LINOLENIC ACID -526.43 -664.83 -138.4
588 AZELAIC ACID -1059.3 -922.44 136.86
589 NEOPENTANOIC ACID -564 -476.4 87.6
590 PENTADECANOIC ACID -861.7 -745.15 116.55
591 2-ETHYL HEXANOIC ACID -635.1 -557.02 78.08
592 n-HEPTANOIC ACID -611.4 -530.15 81.25
593 NEOHEXANOIC ACID -595 -503.27 91.73
594 NEOHEPTANOIC ACID -613.53 -530.15 83.38
595 n-HEPTADECANOIC ACID -924.4 -798.9 125.5
596 NONADECANOIC ACID -984 -852.64 131.36
597 n-EICOSANIC ACID -1011.9 -879.52 132.38
598 FUMARIC ACID -812.2 -734.42 77.78
599 PIMELIC ACID -1009.8 -868.69 141.11
600 SUBERIC ACID -1038 -895.57 142.43
601 CINNAMIC ACID -336.9 -315.67 21.23
602 ACETOXYACETIC ACID -879.7 -788.07 91.63
603 SEBACIC ACID -1082.6 -949.31 133.29
604 ITACONIC ACID -841.1 -761.3 79.8
605 SUCCINIC ACID -940.4 -788.07 152.33
606 GLUTARIC ACID -959.9 -814.94 144.96
607 PYROMELLITIC ACID -1570.8 -1411.82 158.98
Int. J. Mol. Sci. 2007, 8 422

608 IBUPROFEN -559.53 -476.82 82.71

609 METHYL MALEIC ANHYDRIDE -504.55 -511.56 -7.01
610 sec-BUTYL FORMATE -482.76 -476.4 6.36
611 tert-BUTYL FORMATE -499.65 -476.4 23.25
612 n-HEXYL FORMATE -518.49 -530.15 -11.66
613 n-HEPTYL FORMATE -542.98 -557.02 -14.04
614 CYCLOHEXYL FORMATE -495.52 -476.5 19.02
615 tert-BUTYL ACETATE -561.02 -503.27 57.75
616 METHYL ISOBUTYRATE -501.76 -476.4 25.36
617 ETHYL ISOBUTYRATE -538.74 -503.27 35.47
618 ISOPROPYL ACRYLATE -419.4 -449.63 -30.23
619 BENZYL FORMATE -305.13 -342.44 -37.31
620 CETYL METHACRYLATE -742.81 -825.87 -83.06
621 DIMETHYL-2,6-NAPHTHALENEDICARBOXYLATE -709.5 -654.47 55.03
622 CYCLOHEXYL ACETATE -553.48 -503.38 50.1
623 n-NONYL n-UNDECYL PHTHALATE -1140 -1218.48 -78.48
624 DIISONONYL PHTHALATE -1237 -1164.73 72.27
625 DIETHYL PHTHALATE -776.6 -788.48 -11.88
626 DIMETHYL PHTHALATE -677.81 -734.73 -56.92
627 DIETHYL SUCCINATE -913.07 -895.57 17.5
628 DIHEXYL ADIPATE -1161.6 -1164.31 -2.71
629 ETHYLIDENE DIACETATE -865.97 -841.82 24.15
630 DIBUTYL MALEATE -772.2 -949.42 -177.22
631 METHYL DODECANOATE -693 -691.4 1.6
632 DIETHYL MALEATE -798.18 -841.92 -43.74
633 DIMETHYL MALEATE -680.85 -788.17 -107.32
634 DIPROPYL MALEATE -785.11 -895.67 -110.56
635 sec-BUTYL ACRYLATE -436.8 -476.5 -39.7
636 VINYL PIVALATE -429.1 -476.5 -47.4
637 DIMETHYL CARBONATE -607.27 -618.74 -11.47
638 n-PROPYL BENZOATE -397.7 -396.19 1.51
639 ETHYL ISOPROPYL ETHER -315.8 -333.95 -18.15
640 ETHYL n-HEXYL ETHER -381.01 -414.58 -33.57
641 1,3-DIOXANE -377.5 -449.52 -72.02
642 1,2-DIETHOXYETHANE -451.43 -556.92 -105.49
643 2,3-DICHLOROPROPENE -73.3 -84.21 -10.91
644 n-PENTADECYLBENZENE -335.24 -353.27 -18.03
645 n-HEXADECYLBENZENE -414.67 -380.15 34.52
646 n-HEPTADECYLBENZENE -442.5 -407.02 35.48
647 n-OCTADECYLBENZENE -469.9 -433.89 36.01
648 1,3-DICHLOROHEXAFLUOROPROPANE -1321.8 -1347.63 -25.83
649 1,2-DICHLOROHEXAFLUOROCYCLOBUTANE -1282.7 -1320.86 -38.16
650 3,3,3-TRIFLUOROPROPENE -614.2 -635.35 -21.15
651 1,1,2-TRIFLUOROETHANE -675.9 -662.12 13.78
652 PERFLUORO-n-HEXADECANE -7251 -7288.88 -37.88
653 PERFLUOROMETHYLCYCLOPENTANE -2533 -2530.64 2.36
654 1,1,1,2,2-PENTAFLUOROPROPANE -1111 -1092.26 18.74
655 1,1,1,2,3,3-HEXAFLUOROPROPANE -1333 -1293.89 39.11
656 BENZOTRIFLUORIDE -636.7 -581.91 54.79
657 2-BROMOBUTANE -155.1 -137.86 17.24
658 BROMOCHLOROMETHANE -76.01 -84.11 -8.1
659 HALOTHANE -720 -715.87 4.13
660 1,2-DIFLUOROETHANE -447.7 -460.49 -12.79
661 PENTACHLOROFLUOROETHANE -382 -393.24 -11.24
662 1,2-DICHLORO-1,1,2-TRIFLUOROETHANE -735.55 -715.87 19.68
663 2-CHLORO-1,1,1,2-TETRAFLUOROETHANE -924.7 -890.63 34.07
664 1,1-DICHLORO-1-FLUOROETHANE -366.4 -312.61 53.79
665 1,1,1,2-TETRAFLUOROETHANE -895.79 -863.75 32.04
666 HEXAFLUOROACETONE -1460 -1436.33 23.67
667 OCTAFLUOROPROPANE -1783.2 -1697.14 86.06
668 OCTAFLUORO-2-BUTENE -1648 -1670.37 -22.37
669 OCTAFLUOROCYCLOBUTANE -1528 -1670.37 -142.37
670 1,1,1-TRICHLOROFLUOROETHANE -337.1 -339.49 -2.39
Int. J. Mol. Sci. 2007, 8 423

671 1,1,2,2-TETRAFLUOROETHANE -892.4 -863.75 28.65

672 p-BROMOTOLUENE 17.14 -3.9 -21.04
673 n-HEXYL IODIDE -146.4 -191.61 -45.21
674 BROMOTRIFLUOROMETHANE -648.98 -662.12 -13.14
675 DIBROMODIFLUOROMETHANE -386.6 -487.37 -100.77
676 CHLOROTRIFLUOROETHYLENE -555.3 -635.35 -80.05
677 HEXAFLUOROETHANE -1343.9 -1267.01 76.89
678 1-CHLORO-1,1-DIFLUOROETHANE -529.7 -487.37 42.33
679 n-HEXYLAMINE -177.12 -191.61 -14.49
680 n-HEPTYLAMINE -201.33 -218.48 -17.15
681 n-OCTYLAMINE -226.02 -245.36 -19.34
682 n-NONYLAMINE -250.44 -272.23 -21.79
683 n-DECYLAMINE -275.19 -299.11 -23.92
684 n-DODECYLAMINE -368.18 -352.86 15.32
685 CYCLOHEXYL ISOCYANATE -200.64 -253.64 -53
686 N,N'-DI-tert-BUTYLETHYLENEDIAMINE -264.9 -325.98 -61.08
687 DICYCLOHEXYLAMINE -246.4 -245.56 0.84
688 N-METHYLCYCLOHEXYLAMINE -149.52 -164.84 -15.32
689 N-AMINOETHYL ETHANOLAMINE -280.19 -360.83 -80.64
690 PHENYL ISOCYANATE -61.08 -92.7 -31.62
691 ISOQUINOLINE 134.2 130.11 -4.09
692 p-AMINODIPHENYL 81 76.31 -4.69
693 2,6-DIETHYLANILINE -84.23 -84.52 -0.29
694 3-METHYLPYRIDINE 61.9 22.97 -38.93
695 4-METHYLPYRIDINE 59.2 22.97 -36.23
696 ETHYL t-BUTYL SULFIDE -187.3 -191.61 -4.31
697 tert-NONYL MERCAPTAN -266.22 -272.23 -6.01
698 2-METHYLTHIOPHENE 44.6 23.03 -21.57
699 3-METHYLTHIOPHENE 43.1 23.03 -20.07
700 CAMPHOR -319.4 -307.39 12.01
701 N-METHYLFORMAMIDE -241.48 -226.56 14.92
702 DIACETONE ALCOHOL -592.79 -503.27 89.52
703 FURFURYL ALCOHOL -276.2 -342.29 -66.09
704 N,N-DIMETHYLACETAMIDE -278.3 -280.31 -2.01
705 ACETAMINOPHEN -396.04 -369.32 26.72
706 p-METHOXYPHENOL -335.51 -369.21 -33.7
707 2-METHOXYETHANOL -416.32 -476.3 -59.98
708 2-ETHOXYETHANOL -448.22 -503.17 -54.95
709 2-BUTOXYETHANOL -497.4 -556.92 -59.52
710 2-(2-METHOXYETHOXY)ETHANOL -589.99 -726.14 -136.15
711 2-(2-ETHOXYETHOXY)ETHANOL -626.28 -753.01 -126.73
712 2-AMINOETHOXYETHANOL -438.01 -530.05 -92.04
713 ETHYLCHLOROACETATE -509.3 -476.4 32.9
714 2-(2-(2-METHOXYETHOXY)ETHOXY)ETHANOL -786.4 -975.98 -189.58
715 SUCCINIMIDE -460.25 -369.11 91.14
716 4-CARBOXYBENZALDEHYDE -544.91 -484.89 60.02
717 THIOGLYCOLIC ACID -454.56 -422.65 31.91
718 2-HYDROXYETHYL METHACRYLATE -576.15 -645.72 -69.57
719 METHYL LACTATE -643.1 -645.62 -2.52
720 2-METHOXY PROPANOL-1 -449.47 -503.17 -53.7
721 alpha-METHYLBENZYL ALCOHOL FORMATE -347.1 -369.32 -22.22
722 2-FORMYL BENZOIC ACID -531.54 -484.89 46.65
723 2-HYDROXYACETOPHENONE -342.2 -342.44 -0.24
724 4-HYDROXYACETOPHENONE -364.3 -342.44 21.86
725 4-HYDROXYSTYRENE -109.67 -146.35 -36.68
726 ACETYLSALICYLIC ACID -815.6 -707.86 107.74
727 p-PHENETIDINE -172.6 -226.87 -54.27
728 ACETOL -414.15 -422.65 -8.5
729 o-CHLOROPHENOL -172.35 -173.12 -0.77
730 1-ISOPROPOXY-2-PROPANOL -529.6 -556.92 -27.32
731 ISOPHTHALOYL CHLORIDE -367.5 -342.55 24.95
732 4-FORMYLMORPHOLINE -369.9 -449.63 -79.73
733 FLUOSULFONIC ACID -795.78 -712.98 82.8
Int. J. Mol. Sci. 2007, 8 424

734 CHLOROSULFONIC ACID -651.14 -538.22 112.92

735 FERRIC OXIDE -825.5 -1071.38 -245.88
736 ZINC SULFATE -980.14 -947.25 32.89
737 3-ETHYL HEPTANAL -369.5 -387.8 -18.3
738 DIAMYL KETONE -446.5 -441.55 4.95
739 2-BUTYL-1-DECANOL -567.6 -575.82 -8.22
740 2-METHYL-1-TRIDECANOL -566.9 -575.82 -8.92
741 2-METHYL-DODECAN-1-OL -552.6 -548.95 3.65
742 4-METHYL-1-OCTANOL -462.6 -441.45 21.15
743 3-ETHYL-1-HEPTANOL -440.7 -441.45 -0.75
744 THYMOL -277.9 -253.74 24.16
745 1-METHYL-3-HYDROXY-5-ISOPROPYL BENZENE -300 -253.74 46.26
746 1-METHYL-3-HYDROXY-6-ISOPROPYL BENZENE -295 -253.74 41.26
747 trans-1,8-TERPIN -706.9 -610.77 96.13
748 7-METHYL-1-OCTENE -154.5 -191.71 -37.21
749 2-METHYL-1-NONENE -188.7 -218.59 -29.89
750 8-METHYL-1-NONENE -180.2 -218.59 -38.39
751 trans-2-DECENE -187.1 -218.59 -31.49
752 cis-2-DODECENE -233.7 -272.34 -38.64
753 trans-2-DODECENE -239 -272.34 -33.34
754 CYCLOPROPANE CARBOXYLIC ACID -396.5 -395.88 0.62
755 MALONIC ACID -891 -761.19 129.81
756 n-CROTYL ACETATE -410.1 -449.63 -39.53
757 sec-BUTENYL ACETATE -409 -449.63 -40.63
758 VINYLETHYLENE CARBONATE -555.4 -565.2 -9.8
759 DIOCTYL ADIPATE -1266 -1271.81 -5.81
760 DI(2-ETHYLHEXYL)ADIPATE -1265.3 -1271.81 -6.51
761 DODECYL BROMIDE -344.7 -352.86 -8.16
762 1,2-DIBROMODODECANE -367.8 -379.73 -11.93
763 TRIFLUOROIODOMETHANE -589.1 -662.12 -73.02
764 DIFLUOROMETHYL TRIFLUOROMETHYL ETHER -1316 -1261.47 54.53
765 CYCLOPROPANECARBOXAMIDE -190.5 -226.66 -36.16
766 6-AMINOHEXANAMIDE -400.7 -360.93 39.77
767 HEXANAMIDE -423.1 -334.06 89.04
768 TRI-n-OCTYLAMINE -585.01 -675.35 -90.34
769 DIAMYLAMINE -262.21 -299.11 -36.9
770 TRIAMYLAMINE -366.82 -433.48 -66.66
771 UNDECYLAMINE -299.52 -325.98 -26.46
772 NIACIN -344.9 -315.57 29.33
773 L-PHENYLALANINE -466.9 -396.19 70.71
774 DI-2-ETHYLHEXYLAMINE -415.9 -460.35 -44.45
775 BENZIDINE 70.7 49.43 -21.27
776 DICYANDIAMIDE 24.9 -3.8 -28.7
777 DI-tert-BUTYL DISULFIDE -253 -272.23 -19.23
778 DI-tert-BUTYL SULFIDE -232.3 -245.36 -13.06
779 2-METHYLTHIACYCLOPENTANE -105 -111.09 -6.09
780 METHYL ISOPROPYL SULFIDE -123.5 -137.86 -14.36
781 2-ETHYLTHIOPHENE 16.61 -3.85 -20.46
782 2-n-PROPYLTHIOPHENE -8.96 -30.72 -21.76
783 ETHYL PROPYL DISULFIDE -146.2 -191.61 -45.41
784 DIISOPENTYLSULFIDE -282 -299.11 -17.11
785 ETHYLENE GLYCOL 2-ETHYLHEXYL ETHER -597.87 -637.54 -39.67
786 PROPYLENE GLYCOL ETHYL ETHER ACETATE -608.2 -726.24 -118.04
787 DIPROPYLENE GLYCOL t-BUTYL ETHER -801.39 -860.51 -59.12
788 DICHLOROACETIC ACID -496.3 -449.52 46.78
789 PROPYLENE GLYCOL MONOMETHYL ETHER -447.74 -503.17 -55.43
790 DIPROPYLENE GLYCOL MONOMETHYL ETHER -660.85 -779.89 -119.04
791 PROPYLENE GLYCOL 1-tert-BUTYL ETHER -610.36 -583.79 26.57
792 TRIPROPYLENE GLYCOL MONOMETHYL ETHER -884.09 -1056.61 -172.52
793 DIETHYLENE GLYCOL MONOPROPYL ETHER -647.93 -779.89 -131.96
794 2-(2-(2-BUTOXYETHOXY)ETHOXY)ETHANOL -844.47 -1056.61 -212.14
795 2-(2-(2-ETHOXYETHOXY)ETHOXY)ETHANOL -796.01 -1002.86 -206.85
796 2-HEXOXYETHANOL -560.3 -610.67 -50.37
Int. J. Mol. Sci. 2007, 8 425

797 MONOOLEIN -1175 -1244.94 -69.94

798 PROPYLENE GLYCOL n-PROPYL ETHER -506 -556.92 -50.92
799 DIETHYLENE GLYCOL MONOBUTYL ETHER ACETATE -883.71 -1002.96 -119.25
800 3-HYDROXY-2-METHYL PROPIONALDEHYDE -427.87 -476.4 -48.53
801 HYDROXYACETONITRILE -141.77 -172.91 -31.14
802 DIOLEIN -1670 -1817.48 -147.48
803 TRIOLEIN -2161 -2390.03 -229.03
804 sec-BUTENYL GLYCOL ETHER -385.3 -503.27 -117.97
805 SUCROSE -2226.1 -2375.72 -149.62
806 PENTAFLUOROETHYL TRIFLUOROVINYL ETHER -1900 -1866.47 33.53
807 TRIFLUOROMETHYL TRIFLUOROVINYL ETHER -1521 -1463.1 57.9
808 DIPROPYLENE GLYCOL MONOETHYL ETHER -721.6 -806.76 -85.16
809 TRIPROPYLENE GLYCOL MONOETHYL ETHER -957.4 -1083.48 -126.08
810 1-ETHOXY-2-PROPANOL -492.7 -530.05 -37.35
811 1-tert-BUTOXY-2-[2-(HYDROXY)PROPOXY]PROPANE -774.9 -860.51 -85.61
812 METHYL GLYCOLATE -609.4 -618.74 -9.34
813 tert-BUTYL METHACRYLATE -498.2 -557.02 -58.82
814 gamma-AMINOPROPYLTRIETHOXYSILANE -1022 -1153.96 -131.96
815 (3-METHYLACRYLOXYPROPYL)TRICHLOROSILANE -921 -850.58 70.42
816 METHYL DICHLOROSILANE -435.55 -377.56 57.99
817 FERROUS CHLORIDE -341.83 -350.69 -8.86
818 FERRIC CHLORIDE -399.41 -377.56 21.85
819 DIMETHYLCHLOROSILANE -326.35 -377.56 -51.21
820 TRIMETHYLCHLOROSILANE -382.61 -404.43 -21.82
821 DIMETHYLDICHLOROSILANE -480.4 -404.43 75.97
822 DIPHENYLDICHLOROSILANE -238 -244.02 -6.02
823 DICHLORODIETHYLSILANE -530.7 -458.18 72.52
824 ACETOVANILLONE -529.56 -565.41 -35.85
825 VANILLIN -453.4 -538.54 -85.14
826 DIGLYCOLIC ACID -1080.4 -984.16 96.24
827 LEVULINIC ACID -697.05 -618.85 78.2
828 MALIC ACID -1105.4 -984.16 121.24
829 GUAIACOL -325.78 -369.21 -43.43
830 ETHYLENE GLYCOL MONOPROPYL ETHER -473.09 -530.05 -56.96
831 2-(2-BUTOXYETHOXY)ETHANOL -674.4 -806.76 -132.36
832 ETHYLENEDIAMINETETRAACETIC ACID -1759.5 -1680.15 79.35
833 TRICHLOROACETALDEHYDE -234.5 -280.31 -45.81
834 TRICHLOROACETIC ACID -503.3 -476.4 26.9
835 CHLOROACETALDEHYDE -252.69 -226.56 26.13
836 DICHLOROACETALDEHYDE -218.07 -253.43 -35.36
837 ETHYL CHLOROFORMATE -505.2 -449.52 55.68
838 METHOXYACETIC ACID -627.04 -618.74 8.3
839 METHYL CHLOROFORMATE -460.74 -422.65 38.09
840 DEXTROSE -1273.3 -1287.65 -14.35
841 VINYLTRIMETHOXYSILANE -835.9 -965.94 -130.04
842 TRIMETHOXYSILANE -833 -965.84 -132.84
843 TRIMETHYL SILANOL -545.2 -573.65 -28.45
844 ETHYL ALUMINUM SESQUICHLORIDE -970.6 -832.26 138.34
845 SULFAMIC ACID -674.88 -538.22 136.66
846 BIS(CHLOROMETHYL)ETHER -280.58 -307.08 -26.5
847 3-AMINO-1-PROPANOL -291.34 -307.08 -15.74
848 1-AMINO-2-PROPANOL -294.1 -307.08 -12.98
849 ETHYL THIOLACETATE -231.1 -280.31 -49.21
850 ACETOACETANILIDE -403.33 -369.42 33.91
851 LYSINE -678.69 -557.02 121.67
852 DIMETHYL SULFATE -735.5 -761.19 -25.69
853 DIETHYL SULFATE -813.2 -814.94 -1.74
854 L-GLUTAMIC ACID -1009.7 -841.82 167.88
855 ASCORBIC ACID -1164.6 -1180.36 -15.76
856 6-HYDROXYHEXANOIC ACID -779.32 -699.37 79.95
857 CITRIC ACID -1543.8 -1376.45 167.35
858 LACTIC ACID -682.96 -618.74 64.22
859 TARTARIC ACID -1289.5 -1180.25 109.25
Int. J. Mol. Sci. 2007, 8 426

860 HYDROXYCAPROIC ACID -794.19 -699.37 94.82

861 ETHYL LACTATE -695.08 -672.49 22.59
862 2-ETHOXYETHYL ACETATE -663 -699.37 -36.37
863 DIETHYLENE GLYCOL ETHYL ETHER ACETATE -833.64 -949.21 -115.57
864 METHYL ACETOACETATE -642.4 -618.85 23.55
865 ETHYL ACETOACETATE -612.24 -645.72 -33.48
866 METHYL CYANOACETATE -298.3 -369.11 -70.81
867 ETHYL CYANOACETATE -386.49 -395.98 -9.49
868 ETHYL HYDROGEN SULFATE -887.3 -761.19 126.11
869 ACRYLOXY PROPIONIC ACID -786.6 -788.17 -1.57
870 THIODIGLYCOL -477.92 -530.05 -52.13
871 2-MERCAPTOETHANOL -248.94 -280.2 -31.26
872 ETHYLTHIOETHANOL -290.46 -333.95 -43.49
873 DIETHYLETHANOLAMINE -309.5 -387.7 -78.2
874 DIMETHYLETHANOLAMINE -256.97 -333.95 -76.98
875 DIISOPROPANOLAMINE -572.82 -583.79 -10.97
876 3-METHOXYISOPROPYLAMINE -256.2 -333.95 -77.75
877 ETHYLENE GLYCOL MONOBUTYL ETHER ACETATE -710.3 -753.12 -42.82
878 ETHYL VANILLIN -532.3 -565.41 -33.11
879 2-HYDROXYETHYL ACRYLATE -559.87 -618.85 -58.98
880 ETHYL-3-ETHOXYPROPIONATE -684.7 -726.24 -41.54
881 BIS-(2-HYDROXYETHYL) TEREPHTHALATE -1200 -1180.67 19.33
882 DI-(2-CHLOROETHOXY)METHANE -536.2 -583.79 -47.59
883 1-METHYLVINYL ACETATE -390.1 -422.75 -32.65
884 2-PENTOXYETHANOL -528.2 -610.67 -82.47
885 1-CHLORO-3-PROPANOL -343.7 -307.08 36.62
886 TRIFLUOROACETAMIDE -935.3 -831.45 103.85
887 DILACTIDE (dl) -792.1 -788.17 3.93
888 2-(2-PENTOXYETHOXY)ETHANOL -725.7 -833.64 -107.94
889 METHYL-4-FORMYLBENZOATE -476.1 -511.76 -35.66
890 HYDROXYPIVALYL HYDROXYPIVALATE -1003 -1002.96 0.04
891 TETRAETHYLENE GLYCOL MONOBUTYL ETHER -1032 -1306.45 -274.45
892 METHYL para-TOLUATE -390.7 -369.32 21.38

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.
Int. J. Mol. Sci. 2007, 8 427

Table 4. The predicted ∆H f by the Eq. (2) for test set as an excluded data set.
o

∆Hfo(kJ/mol)
ID Name Res
DIPPR 801 Calculated from Eq. (2)

1 2-METHYLPENTANE -204.64 -164.73 39.91

2 2-METHYLHEXANE -229.49 -191.61 37.88
3 n-OCTANE -249.78 -218.48 31.3
4 3-METHYLHEPTANE -252.34 -218.48 33.86
5 2,5-DIMETHYLHEXANE -260.37 -218.48 41.89
6 3,4-DIMETHYLHEXANE -251.83 -218.48 33.35
7 2,2,3,3-TETRAMETHYLBUTANE -268.61 -218.48 50.13
8 2,2,5-TRIMETHYLHEXANE -293.3 -245.36 47.94
9 2,2,3,4-TETRAMETHYLPENTANE -277.7 -245.36 32.34
10 2,3,3,4-TETRAMETHYLPENTANE -277.9 -245.36 32.54
11 2,2,3,3-TETRAMETHYLHEXANE -303.47 -272.23 31.24
12 n-HEPTADECANE -479.86 -460.35 19.51
13 2,2-DIMETHYLOCTANE -313.12 -272.23 40.89
14 n-EICOSANE -623.61 -540.98 82.63
15 n-TETRACOSANE -739.31 -648.48 90.83
16 3-METHYLNONANE -303.59 -272.23 31.36
17 4-METHYLNONANE -304.1 -272.23 31.87
18 2-METHYLOCTANE -280.6 -245.36 35.24
19 ISOPROPYLCYCLOPENTANE -190.09 -164.84 25.25
20 n-BUTYLCYCLOPENTANE -214.2 -191.71 22.49
21 n-BUTYLCYCLOHEXANE -263.09 -218.59 44.5
22 BICYCLOHEXYL -273.7 -218.69 55.01
23 cis-2-PENTENE -53.49 -84.21 -30.72
24 trans-2-PENTENE -57.98 -84.21 -26.23
25 2-METHYL-2-BUTENE -68.07 -84.21 -16.14
26 trans-3-HEXENE -86.06 -111.09 -25.03
27 3-METHYL-cis-2-PENTENE -94.47 -111.09 -16.62
28 2,3-DIMETHYL-2-BUTENE -102.42 -111.09 -8.67
29 4-METHYL-1-HEPTENE -126.1 -164.84 -38.74
30 trans-2-OCTENE -135 -164.84 -29.84
31 2,4,4-TRIMETHYL-2-PENTENE -142.42 -164.84 -22.42
32 1-DECENE -172.3 -218.59 -46.29
33 1-PENTADECENE -301.12 -352.96 -51.84
34 1-HEPTADECENE -349.83 -406.71 -56.88
35 1-NONADECENE -399.59 -460.46 -60.87
36 p-tert-BUTYL ETHYLBENZENE -131.46 -111.4 20.06
37 m-DIISOPROPYLBENZENE -132.4 -111.4 21
38 1,2,4-TRIETHYLBENZENE -134.05 -111.4 22.65
39 HEXAETHYLBENZENE -329.6 -272.65 56.95
40 p-TERPHENYL 150.25 156.52 6.27
41 TRIPHENYLMETHANE 171.2 129.64 -41.56
Int. J. Mol. Sci. 2007, 8 428

42 2-METHYLINDENE 60.78 49.64 -11.14

43 INDENE 110.42 76.52 -33.9
44 PENTANAL -267.3 -280.31 -13.01
45 3-METHYLHEXANAL -315.39 -334.06 -18.67
46 TRIDECANAL -470.62 -495.3 -24.68
47 GLYCOL ALDEHYDE -404.2 -395.78 8.42
48 METHACROLEIN -145.04 -199.79 -54.75
49 p-TOLUALDEHYDE -120.56 -146.35 -25.79
50 BENZALDEHYDE -86.82 -119.47 -32.65
51 SALICYLALDEHYDE -265.7 -315.57 -49.87
52 m-TOLUALDEHYDE -123.4 -146.35 -22.95
53 PARALDEHYDE -673.2 -699.37 -26.17
54 ACETONE -248.1 -226.56 21.54
55 3-PENTANONE -296.51 -280.31 16.2
56 5-HEXEN-2-ONE -197.4 -253.54 -56.14
57 2-PENTANONE -297.29 -280.31 16.98
58 METHYL ISOPROPYL KETONE -299.5 -280.31 19.19
59 2-HEPTANONE -348.2 -334.06 14.14
60 5-METHYL-2-HEXANONE -350.93 -334.06 16.87
61 ISOPHORONE -301.4 -280.51 20.89
62 gamma-BUTYROLACTONE -420.9 -395.88 25.02
63 epsilon-CAPROLACTONE -477.36 -449.63 27.73
64 gamma-VALEROLACTONE -461.3 -422.75 38.55
65 ETHYL ISOPROPYL KETONE -325.9 -307.18 18.72
66 METHYL ISOPROPENYL KETONE -216.79 -226.66 -9.87
67 2-METHYL-1-PROPANOL -334.7 -307.08 27.62
68 2-METHYL-2-BUTANOL -379.5 -333.95 45.55
69 2-METHYL-1-PENTANOL -383.8 -360.83 22.97
70 3-METHYL-3-PENTANOL -404.93 -360.83 44.1
71 3-METHYL-2-BUTANOL -366.64 -333.95 32.69
72 2-HEPTANOL -410.72 -387.7 23.02
73 5-METHYL-1-HEXANOL -404.31 -387.7 16.61
74 4-METHYL-2-PENTANOL -394.7 -360.83 33.87
75 1-OCTANOL -426.5 -414.58 11.92
76 2-OCTANOL -442.92 -414.58 28.34
77 2-NONANOL -467.91 -441.45 26.46
78 1-HEXADECANOL -686.3 -629.57 56.73
79 1-OCTADECANOL -750 -683.32 66.68
80 1-EICOSANOL -827 -737.07 89.93
81 1-NONADECANOL -785.33 -710.2 75.13
82 CYCLOHEXANOL -348.6 -307.18 41.42
83 trans-2-METHYLCYCLOHEXANOL -416.1 -334.06 82.04
84 L-MENTHOL -479.43 -414.68 64.75
85 beta-TERPINEOL -369.2 -361.03 8.17
86 2-METHYL-1-UNDECANOL -514.5 -522.07 -7.57
87 ALLYL ALCOHOL -171.1 -226.56 -55.46
88 2,4-XYLENOL -228.78 -199.99 28.79
Int. J. Mol. Sci. 2007, 8 429

89 p-CRESOL -199.28 -173.12 26.16

90 TRIETHYLENE GLYCOL -804.2 -949.11 -144.91
91 NEOPENTYL GLYCOL -551.2 -530.05 21.15
92 TRIPROPYLENE GLYCOL -921.41 -1029.73 -108.32
93 1,2,3-BUTANETRIOL -764.1 -699.26 64.84
94 1,2,4-BUTANETRIOL -745.1 -699.26 45.84
95 1,4-BUTANEDIOL -503.3 -503.17 0.13
96 INOSITOL -1362.1 -1287.65 74.45
97 2-METHYLBUTYRIC ACID -554.5 -476.4 78.1
98 n-TRIDECANOIC ACID -806.6 -691.4 115.2
99 n-TETRADECANOIC ACID -833.5 -718.27 115.23
100 cis-CROTONIC ACID -347.27 -395.88 -48.61
101 2-METHYLOCTANOIC ACID -661.6 -583.9 77.7
102 METHACRYLIC ACID -408.09 -395.88 12.21
103 BENZOIC ACID -385.2 -315.57 69.63
104 o-TOLUIC ACID -416.5 -342.44 74.06
105 PHTHALIC ACID -782.07 -680.98 101.09
106 ISOPHTHALIC ACID -803 -680.98 122.02
107 ETHYL FORMATE -420.5 -422.65 -2.15
108 METHYL ACETATE -445.8 -422.65 23.15
109 n-PROPYL n-BUTYRATE -554.1 -530.15 23.95
110 METHYL n-BUTYRATE -490 -476.4 13.6
111 n-BUTYL ACRYLATE -433.45 -476.5 -43.05
112 BENZYL BENZOATE -273.1 -289.11 -16.01
113 ETHYLENE CARBONATE -586.3 -565.1 21.2
114 n-NONYL ACETATE -654.12 -637.65 16.47
115 2-ETHYLHEXYL ACRYLATE -526.06 -584 -57.94
116 ETHYLENE GLYCOL DIACETATE -865.43 -841.82 23.61
117 ISOBUTYL METHACRYLATE -465.16 -503.38 -38.22
118 METHYL DECANOATE -640.5 -637.65 2.85
119 DIMETHYL-1,4-CYCLOHEXANEDICARBOXYLATE -948.9 -895.67 53.23
120 METHYL ISOPROPYL ETHER -278.7 -307.08 -28.38
121 METHYL tert-PENTYL ETHER -339.86 -360.83 -20.97
122 ISOPROPYL ISOBUTYL ETHER -370.63 -387.7 -17.07
123 DIETHYLENE GLYCOL DIETHYL ETHER -638.4 -806.76 -168.36
124 2,3,4,5,2',3',4',5'-OCTAHYDRO-BIFURYL-(3,3') -390.5 -503.38 -112.88
125 CARBON TETRACHLORIDE -128.41 -137.86 -9.45
126 3-CHLOROPROPENE -30.8 -57.34 -26.54
127 1,4-DICHLORO-cis-2-BUTENE -105.65 -111.09 -5.44
128 m-CHLOROBENZOYL CHLORIDE -189.7 -173.22 16.48
129 1,3-DICHLORO-trans-2-BUTENE -122.25 -111.09 11.16
130 CHLOROFLUOROMETHANE -264 -258.86 5.14
131 CHLORODIFLUOROMETHANE -481.6 -460.49 21.11
132 2-CHLORO-1,1-DIFLUOROETHYLENE -329 -433.72 -104.72
133 PERFLUORO-n-OCTANE -3860 -3847.81 12.19
134 METHYL BROMIDE -37.7 -57.23 -19.53
135 PENTAFLUOROETHANE -1100.4 -1065.38 35.02
Int. J. Mol. Sci. 2007, 8 430

136 BROMOBENZENE 60.7 22.97 -37.73

137 1,1-DICHLOROTETRAFLUOROETHANE -926.8 -917.5 9.3
138 DICHLOROFLUOROMETHANE -283.3 -285.74 -2.44
139 1-BROMONAPHTHALENE 116.39 103.23 -13.16
140 n-BUTYLAMINE -127.7 -137.86 -10.16
141 ISOPROPYLAMINE -112.3 -110.98 1.32
142 n-TETRADECYLAMINE -424.7 -406.6 18.1
143 MONOETHANOLAMINE -274.47 -280.2 -5.73
144 HEXANENITRILE -57.29 -84.32 -27.03
145 ETHYL MERCAPTAN -73.6 -84.11 -10.51
146 n-PROPYL MERCAPTAN -99.9 -110.98 -11.08
147 ISOPROPYL MERCAPTAN -105.9 -110.98 -5.08
148 METHYL t-PENTYL SULFIDE -179.99 -191.61 -11.62
149 DIETHYL SULFIDE -119.4 -137.86 -18.46
150 DI-n-PROPYL DISULFIDE -171.5 -218.48 -46.98
151 PHENYL MERCAPTAN 63.7 22.97 -40.73
152 SULFOLANE -441.64 -369.11 72.53
153 CARBONYL FLUORIDE -638.9 -576.07 62.83
154 DICHLOROACETYL CHLORIDE -280.4 -280.31 0.09
155 CHLOROMETHYL METHYL ETHER -236 -280.2 -44.2
156 6-AMINOHEXANOL -400 -387.7 12.3
157 3-MERCAPTOPROPIONIC ACID -468.36 -449.52 18.84
158 o-CHLOROBENZOIC ACID -404.83 -342.44 62.39
159 ACETONE CYANOHYDRIN -196.28 -226.66 -30.38
160 DICHLOROSILANE -320.49 -350.69 -30.2
161 BIS[3-(TRIETHOXYSILYL)PROPYL]DISULFIDE -2158 -2304.44 -146.44
162 3-NONANONE -397.4 -387.8 9.6
163 4-NONANONE -398.3 -387.8 10.5
164 2,6,8-TRIMETHYL-4-NONANONE -490.9 -468.43 22.47
165 2,7-DIMETHYLOCTANE -311.3 -272.23 39.07
166 1-PHENYL-2-PROPANOL -220.17 -226.87 -6.7
167 2-PHENYL-1-PROPANOL -223 -226.87 -3.87
168 p-TOLUALCOHOL -209.27 -199.99 9.28
169 DINONYLPHENOL -682.28 -629.99 52.29
170 CITRACONIC ACID -824.46 -761.3 63.16
171 2-ETHYL BUTYRIC ACID -599.99 -503.27 96.72
172 PROPYLENE CARBONATE -613.2 -591.97 21.23
173 GLYCERYL TRIACETATE -1330.8 -1260.98 69.82
174 DI-n-BUTYL PHTHALATE -842.6 -895.98 -53.38
175 ISOBUTYL ACRYLATE -438.95 -476.5 -37.55
176 DIISOBUTYL ETHER -387.92 -414.58 -26.66
177 ETHYLAL -450.41 -530.05 -79.64
178 PERFLUORO-n-PENTANE -2608 -2557.41 50.59
179 PERFLUORO-n-HEPTANE -3338 -3417.68 -79.68
180 1,1,1,2,3,3,3-HEPTAFLUOROPROPANE -1552 -1495.51 56.49
181 2,2-DICHLORO-1,1,2-TRIFLUOROETHANE -728.38 -715.87 12.51
182 1,1,2-TRICHLOROTRIFLUOROETHANE -805.8 -742.75 63.05
Int. J. Mol. Sci. 2007, 8 431

183 BROMOCHLORODIFLUOROMETHANE -431.37 -487.37 -56

184 CHLOROPENTAFLUOROETHANE -1123 -1092.26 30.74
185 CYCLOPENTYLAMINE -95.14 -111.09 -15.95
186 N,N'-DIPHENYL-p-PHENYLENEDIAMINE 169.08 102.77 -66.31
187 ISOPHORONE DIISOCYANATE -429 -503.69 -74.69
188 METHYL n-BUTYL SULFIDE -142.9 -164.73 -21.83
189 tert-DODECYL MERCAPTAN -338.83 -352.86 -14.03
190 TRIACETONE ALCOHOL -690.06 -779.99 -89.93
191 4-HYDROXYBUTYRALDEHYDE -417.22 -449.52 -32.3
2,2,4-TRIMETHYL-1,3-PENTANEDIOL
192 MONOISOBUTYRATE -903 -860.62 42.38
193 p-CHLOROPHENOL -197.7 -173.12 24.58
194 2-CHLOROETHANOL -307.85 -280.2 27.65
195 CHROMIUM TRIOXIDE -578.23 -724.28 -146.05
196 FERROUS SULFATE -928.85 -947.25 -18.4
197 ZINC OXIDE -347.82 -439.38 -91.56
198 6-METHYL-1-OCTANOL -463.5 -441.45 22.05
199 cis-1,8-TERPIN -709.6 -610.77 98.83
200 cis-2-DECENE -182.9 -218.59 -35.69
2,2,4-TRIMETHYL-1,3-PENTANEDIOL
201 DIISOBUTYRATE -1118 -1110.56 7.44
202 DIMETHYL SUCCINATE -845.1 -841.82 3.28
BENZENE-1,2,4-TRICARBOXYLIC ACID
203 TRIMETHYL ESTER -1055 -1127.02 -72.02
204 DIMETHYLMALONATE -784.8 -814.94 -30.14
205 DIFLUOROMETHYL METHYL ETHER -642.8 -656.59 -13.79
206 DI-n-OCTYLAMINE -407.3 -460.35 -53.05
207 2-PENTANETHIOL -151.6 -164.73 -13.13
208 DI-n-BUTYL SULFIDE -220.5 -245.36 -24.86
209 PROPYLENE GLYCOL 2-tert-BUTYL ETHER -573.91 -583.79 -9.88
210 2-(2-HEXOXYETHOXY)ETHANOL -742.7 -860.51 -117.81
211 DIPROPYLENE GLYCOL n-PROPYL ETHER -737.7 -833.64 -95.94
212 CROTYL GLYCOL ETHER -386.6 -503.27 -116.67
213 DIETHYLSULFITE -600.43 -672.49 -72.06
214 DIMETHYLDIMETHOXYSILANE -715.46 -796.62 -81.16
215 PYRUVIC ACID -581.41 -565.1 16.31
216 METHYL CHLOROACETATE -495.6 -449.52 46.08
217 PERFLUOROBUTANOIC ACID -1924 -1860.93 63.07
218 TRIDECAFLUOROHEPTANOIC ACID -3215 -3151.33 63.67
219 tert-BUTYLFORMAMIDE -340.98 -307.18 33.8
220 METHYLETHANOLAMINE -254.59 -307.08 -52.49
221 2-HYDROXYPROPYL METHACRYLATE -629.34 -530.15 99.19
222 2-HYDROXYPROPYL ACRYLATE -582.5 -645.72 -63.22
223 METHOXYACETONE -383.4 -449.52 -66.12
Int. J. Mol. Sci. 2007, 8 432

Acknowledgment

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

References

1. Benson S.W. Thermochemical Kinetics; Wiley, New York, 1968.

2. Joback, K.G.; Reid R.C. Estimation of pure-component properties from group contributions.
Chem. Eng. Comm. 1987, 57, 233.
3. Constantinou L.; Gani R. New group contribution method for estimating properties of pure
compound. AIChE J. 1994, 40, 1697.
4. Katritzky A.R.; Fara D.C. How chemical structure determines physical, chemical, and
technological properties: an overview illustrating the potential of quantitative structure-property
relationships for fuels science. Energy & Fuels 2005, 19, 922.
5. Taskinen J.; Yliruusi J. Prediction of physicochemical properties based on neural network
modeling. Adv. Drug Delivery Rev. 2003, 55, 1163.
6. Design Institute for Physical Properties Research (DIPPR), American Institute of Chemical
Engineers, Project 801, 2006.
7. Hyperchem Release 7.5 for Windows, Molecular Modeling System, Hypercube, Inc., 2002.
8. Talete srl, Dragon for Widows (Software for Molecular Descriptor Calculation). Version 5.4-2006-
http://www.talete.mi.it/.
9. Leardi, R.; Boggia, R.; Terrile M. Genetic algorithms as strategy for feature selection.
J. Chemometrics 1992, 6, 267.
10. Gharagheizi, F. QSPR analysis for intrinsic viscosity of polymer solutions by means of
GA-MLR and RBFNN. Comput. Mater. Sci. (In press) doi: 10.1016/j.commatsci.2006.11.010.
11. Gharagheizi, F. QSPR studies for solubility parameter by means of genetic algorithm-based
multivariate linear regression and generalized regression neural network. QSAR Comb. Sci.
(In Press) doi: 10.1002/qsar.200630159.
12. Gharagheizi, F.; Mehrpooya, M.; Vatani, A. Prediction of standad chemical exergy by a three-
descriptors QSPR model. Energ. Convers. Manage. (In Press)
doi:10.1016/j.enconman.2007.04.005.
13. Todeschini R.; Consonni, V.; in Manhold, R.; Kubinyi, H.; Temmerman, H. (Series editors),
Handbook of molecular descriptors, Weinheim, New York, Wiley-VCH, (2000).

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