J Therm Anal Calorim (2014) 117:433–437
DOI 10.1007/s10973-014-3675-9
The standard molar enthalpies of formation of chromone-3-
carboxylic acid, 6-methylchromone-2-carboxylic acid, and
6-methyl-4-chromanone determined by micro-combustion
calorimetry
Henoc Flores • Arturo Ximello • E. Adriana Camarillo
Patricia Amador
Received: 7 November 2013 / Accepted: 28 January 2014 / Published online: 25 February 2014
Ó Akadémiai Kiadó, Budapest, Hungary 2014
Abstract The energies of combustion of chromone-3-
carboxylic acid (C3CA), 6-methylchromone-2-carboxylic
acid (6MCC), and 6-methyl-4-chromanone (6M4C) were
determined using an isoperibolic micro-combustion calo-
rimeter. The calorimeter used in the present work has been
assembled, calibrated, and tested in our laboratory with the
desired results. Prior to the measurement of the energies of
combustion, the purities, heat capacities (Cp), fusion tem-
peratures (Tfus), and enthalpies of melting (DfusH) for each
compound were determined by differential scanning calo-
rimetry. The values of the energies of combustion were used
to derive standard molar enthalpies of combustion (Dc Hm )
and standard molar enthalpies of formation (Df Hm ) in the
crystalline phase at T = 298.15 K. The values found for the
Df Hm of C3CA, 6MCC, and 6M4C were -(619.5 ± 2.6),
-(656.2 ± 2.2), and -(308.9 ± 3.0) kJ mol-1, respectively.
Keywords Micro-combustion calorimetry  Combustion
energies  Enthalpies of formation  Chromone-3-
carboxylic acid  6-Methylchromone-2-carboxylic acid 
6-Methyl-4-chromanone
Electronic supplementary material The online version of this
article (doi:10.1007/s10973-014-3675-9) contains supplementary
material, which is available to authorized users.
H. Flores (&)  A. Ximello  E. A. Camarillo  P. Amador
Facultad de Ciencias Quı́micas de la Benemérita, Universidad
Autónoma de Puebla, 14 Sur y Av. San Claudio, 72570 Puebla,
PUE, Mexico
e-mail: henoc.flores@correo.buap.mx
•
Introduction
The chromones, widely known as 1,4-benzopyranes or
c-benzopyrones, are cyclic compounds consisting of nine
carbon atoms with sp2 hybridization. The special structure
of chromones makes them suitable for a wide range of
practical applications, many of them due also to their
biological activity, for example, their activity as inhibitors
of the tyrosine-specific protein kinases and of the protein
kinase C. Chromones act also as fungicides, antiviral,
antihypertensive, anti-inflammatory, antioxidant, anti-
thrombotic, immunomodulatory, and anticarcinogenic
agents [1]. In particular, chromones are used as reagents for
the synthesis of 3-acyl-4-hydroxycoumarins [2] and oxa-
zepina, which is a therapeutic agent effective in the treat-
ment of viral diseases [3], among others. On the other hand,
some derivatives of chromanone have been found to
exhibit insecticidal, antifungal, and antibacterial activity,
and they may be used also as perfuming ingredients [4–6].
It has been shown that some derivatives, like 6-methyl-4-
chromanone (6M4C), have strong activity in inhibiting
in vitro cell growth of human K562 cells [7].
It should be noted that there exists one report of the
enthalpy of formation of chromone (the unsubstituted com-
pound) [8, 9] and another one for chromone-3-carboxylic acid
(C3CA), which gives a value of -(626.3 ± 2.3) kJ mol-1
[10]; both measurements were made by static-bomb com-
bustion calorimetry. No reports were found for the enthalpy
of formation of 6-methylchromone-2-carboxylic acid
(6MCC) and 6M4C.
On other hand, micro-combustion calorimetry has
shown to be, in our laboratory, a reliable technique for
determining the energies of combustion of many organic
compounds when the available amount of the substance is
small [11–15].
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434 H. Flores et al.

Fig. 1 Chromone derivatives O

studied in this work: chromone-
O O O
3-carboxylic acid,
6-methylchromone-2-carboxylic
acid, and 6-methyl-4- OH OH
chromanone O

O O O

(C3CA) (6MCC) (6M4C)

Table 1 Physical properties of the compounds under study and of all the materials which took part in the combustion processes at T = 298.15 K
Compound Ma/g mol-1 xf Tfus/K DfusH /kJ mol-1 Cp/J g-1 K-1 q/g cm-3 ðou=opÞT /J g-1 MPa-1

C3CA 190.15 0.9991 ± 0.0001b 475.42 ± 0.10 33.70 ± 0.33 1.17 ± 0.01b 1.30b 0.2e
6MCC 204.18 0.99c 1.14 ± 0.02b 1.06b 0.2e
b b b
6M4C 162.19 0.9923 ± 0.0013 307.78 ± 0.08 14.88 ± 0.21 1.23 ± 0.02 1.07 0.2e
d d
Benzoic acid 122.12 1.209 1.320 0.115d
d d
Cotton 28.18 1.674 1.5 0.289d
The parameters obtained from the DSC analysis are also given
a
Molar masses are based on the 2007 IUPAC recommendations [20]
b
Experimental values
c
Supplier value
d
Taken form Ref. [21]
e
Typical value for organic compounds [22]
f
x is the molar fraction

The aim of the present work was the experimental
determination of the energies of combustion and the deri-
vation of the standard enthalpies of formation in the solid
state of C3CA, 6MCC, and 6M4C. The structures of these
compounds are shown in Fig. 1.
Experimental
C3CA, 6MCC, and 6M4C are commercial products and
were supplied by Aldrich Co.
The determinations of the purities, heat capacities,
melting temperatures, and enthalpies of melting were car-
ried out with a differential scanning calorimeter (DSC)
2010 TA Instruments.
This equipment has a sensitivity of 0.001 mW and a
temperature control of ±0.1 K. All the experiments per-
formed with the DSC were carried out under a constant
flow of dry nitrogen in order to have an inert atmosphere.
The cells containing the samples during the DSC mea-
surements were non-hermetic aluminum cells. To minimize
systematic errors, the DSC calibration constant and tem-
perature corrections were obtained by the fusion of high-
purity indium [16]. The purity of the compounds was
determined by the fractional melting technique and the heat
capacities, by comparison with measurements for a
synthetic sapphire sample (continuous method or three
steps method) [17, 18]. Table 1 shows the physical prop-
erties of all the components which took part in the com-
bustion processes and some of the properties of the
chromones determined by DSC. Table A, in supplementary
material, shows heat capacities values on the temperature
range of 283.15–313.15 K for compounds studied here.
The combustion experiments were carried out in an
isoperibolic micro-combustion calorimeter, which was
built, calibrated, and tested in our laboratory [9], and has as
its central component a 1107 semi-micro combustion bomb
(Parr Instrument Co.). The bomb has an internal volume of
22 cm3 and can be utilized to determine energies of com-
bustion of liquid and solid samples with a mass of up to
40 mg.
The crucible of platinum has a mass of about 0.22804 g.
The crucible, which contains the sample, is placed inside
the bomb and the device is assembled in such a way that
the platinum wire (25 mm long) which will close the
ignition circuit is in contact with the sample through a
cotton thread (27 mm long). The cotton thread fuse used in
this work has the empirical formula C1H1.742O0.921 and a
massic energy of combustion Dcu°(cotton) =
-1
-(16.9452 ± 0.0042) kJ g [19]. Finally, 0.1 cm3 of
demineralized water was added to the bomb before closing.
Further details about the experimental procedure, and the

123
Formation of C3CA, 6MCC and 6M4C 435

Table 2 Results of combustion experiments for chromone-3-carboxylic acid at T = 298.15 K and p° = 0.1 MPa
m (cpd)/g 0.04063 0.03994 0.03850 0.04011 0.04033 0.04049 0.04042
m (cotton)/g 0.00049 0.00053 0.00066 0.00075 0.00053 0.00074 0.00064
m (Pt)/g 0.23220 0.23298 0.23257 0.23214 0.23178 0.23219 0.23188
Ti/K 298.1550 298.1540 298.1535 298.1543 298.1531 298.1534 298.1549
Tf/K 298.9272 298.8850 298.8575 298.8944 298.8944 298.9010 298.9074
DTad/K 0.7061 0.6943 0.6716 0.7017 0.7023 0.7076 0.7036
ei (cont.)/kJ K-1 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011
-1
ef (cont.)/kJ K 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011
e calor (-DT)/kJ -0.9042 -0.8891 -0.8601 -0.8986 -0.8994 -0.9062 -0.9010
e cont (-DT)/kJ -0.0009 -0.0008 -0.0008 -0.0009 -0.0009 -0.0009 -0.0009
(-UIBP)/kJ 0.9009 0.8857 0.8567 0.8953 0.8961 0.9029 0.8977
(DUign)/kJ 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042
DUR/kJ 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008
(-mDcu°) (cotton)/kJ 0.0083 0.0090 0.0113 0.0128 0.0090 0.0125 0.0108
(-mDcu°) (cpd)/kJ 0.8918 0.8759 0.8446 0.8817 0.8863 0.8896 0.8861
(-Dcu°) (cpd)/kJ g-1 21.9493 21.9304 21.9377 21.9820 21.9762 21.9709 21.9223
h-Dcu°(298.15 K) kJ g-1i = 21.9527 ± 0.0090
m (cpd), mass of compound; m (cotton), mass of the cotton thread; m (Pt), mass of platinum which includes crucible and wire for ignition; DTc,
corrected temperature rise; e (cont.), energy equivalent of the bomb contents and was calculated as: e cont (-DT) = ei cont
(Ti - 298.15 K) ? efcont (298.15 - Tf ? DTcorr); DUign, ignition energy; DUIBP, energy of the isothermal bomb process, calculated as:
DUIBP =: e cont (-DT) ? e calor (-DT) ? DUign; DUR, correction to standard states, Dcu°(cpd), massic energy of combustion, calculated as:
Dcu°(cpd) = [DUIBP ? DUdec (HNO3) ? DUR - (mDcu°) (cotton)]/m (cpd)

Table 3 Results of combustion experiments for 6-methylchromone-2-carboxylic acid at T = 298.15 K and p° = 0.1 MPa
m (cpd)/g 0.03828 0.04008 0.04024 0.04064 0.03970 0.04158 0.04118 0.04002
m (cotton)/g 0.00067 0.00072 0.00074 0.00084 0.00076 0.00073 0.00065 0.00074
m (Pt)/g 0.23240 0.23202 0.23364 0.23216 0.23155 0.23240 0.23157 0.23198
Ti/K 298.1553 298.1546 298.1529 298.1548 298.1522 298.1527 298.1531 298.1530
Tf/K 298.9113 298.9432 298.9454 298.9507 298.9319 298.9766 298.9657 298.9408
DTad/K 0.7173 0.7509 0.7537 0.7629 0.7442 0.7784 0.7700 0.7502
ei (cont.)/kJ K-1 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011
ef (cont.)/kJ K-1 0.0012 0.0012 0.0012 0.0012 0.0012 0.0012 0.0012 0.0012
e calor (-DT)/kJ -0.9186 -0.9616 -0.9652 -0.9770 -0.9530 -0.9968 -0.9861 -0.9607
e cont (-DT)/kJ -0.0010 -0.0010 -0.0010 -0.0010 -0.0010 -0.0010 -0.0010 -0.0010
(-DUIBP)/kJ 0.9154 0.9584 0.9620 0.9738 0.9498 0.9936 0.9829 0.9575
(DUign)/kJ 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042
DUR/kJ 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008
(-mDcu°) (cotton)/kJ 0.0114 0.0122 0.0125 0.0142 0.0129 0.0123 0.0110 0.0125
(-mDcu°) (cpd)/kJ 0.9032 0.9454 0.9487 0.9588 0.9361 0.9805 0.9711 0.9442
(-Dcu°) (cpd)/kJ g-1 23.5946 23.5878 23.5760 23.5925 23.5793 23.5810 23.5818 23.5932
h-Dcu°(298.15 K) kJ g-1i = 23.5858 ± 0.0025
The symbols have the same meaning than Table 2

calibration and test of the micro-combustion calorimeter
can be found in Refs. [9, 10].
To remove atmospheric nitrogen, the bomb was flushed
by charging it with oxygen up to 1.0 MPa and then
reducing the pressure to atmospheric pressure and repeat-
ing this process repeatedly, for 10 min. Finally,
combustion is started by a spark generated by a Parr 2901
ignition unit of 115 V, which at the time of the ignition
provides a quantity of energy of 4.184 J.
After assembling, the calorimetric system is put into the
chamber of a Lauda RK20 circulator which keeps a constant
temperature of (300.150 ± 0.001) K. During the combustion

123
436 H. Flores et al.

experiments, the temperature rise was monitored with a 5610 The corrected temperature rise, the correction of
Hart Scientific thermistor, (calibrated over a range of apparent mass to mass, and the Washburn corrections were
273.15–373.15 K) which was connected to an HP 34420A calculated by using computational programs written in our
digital multimeter with a sensitivity of 10-6 kW. This, in turn, laboratory on the basis of existing literature [24–26].
was connected to a PC to record data automatically. Since the
semi-micro combustion bomb had been previously repaired and
some of its parts replaced, a new calibration of the calorimetric
system was necessary and it was carried out by means of Results
combustion runs using benzoic acid (supplied by NIST as
standard reference material 39j with a certified energy of com- Our results for the standard energies of combustion of
bustion Dcu = -(26,434 ± 3) J g-1 under the standard bomb C3CA, 6MCC, and 6M4C are given in Tables 2, 3, and 4
conditions) as standard substance. Due to significant differences and they correspond, respectively, to the following ideal-
between the combustion conditions in our micro-combustion ized reactions:
calorimeter and the certification standard bomb conditions, it C10 H6 O4 ðcr) þ 9:5 O2 ðgÞ ¼ 10 CO2 ðg) þ 3H2 O(l) ð1Þ
was necessary to make appropriate Washburn corrections [23].
C11 H8 O4 ðcr) þ 11 O2 ðg) ¼ 11 CO2 ðg) þ 4H2 O(l) ð2Þ
From six calibration runs, the calorimetric equivalent was
determined as e (calor) = (1.2806 ± 0.0004) kJ K-1. The C10 H10 O2 ðcr) þ 11:5 O2 ðg) ¼ 10 CO2 ðg) þ 5 H2 O(l) ð3Þ
combustion experiments and the calibration of the calorimeter
were carried out using the same procedure. All the masses were The standard molar energies of combustion (Dc Um ),
measured using a Mettler Toledo UMX2 balance with an standard molar enthalpies of combustion (Dc Hm ), and stan-
accuracy of ±10-7 g.
dard molar enthalpies of formation (Df Hm ) in the crystalline
At the end of each combustion run, the resultant solution
phase of C3CA, 6MCC and 6M4C are given in Table 5. The
and the bomb-rinsing water were carefully collected and
uncertainty is the overall standard deviation of the mean,
examined to determine their content of nitric acid. The
which includes the random errors in the calorimetric con-
volumetric method was applied and a standardized disso-
stant and in the energies of combustion of benzoic acid, of
lution of NaOH for titration was used. Additionally, De-
the auxiliary materials, and of the substance itself [27]. The
varda’s alloy method was used. In no case was an
values for the standard molar enthalpies of formation of
appreciable quantity of nitric acid detected. This fact was
CO2 (g), (-393.51 ± 0.13) kJ mol-1, and H2O (l),
due to the high-purity oxygen used in the combustion
(-285.83 ± 0.042) kJ mol-1, at T = 298.15 K were taken
experiments and to the exhaustive flushing of the bomb
from CODATA [28].
before filling it.

Table 4 Results of combustion experiments for 6-methyl-4-chromanone at T = 298.15 K and p8 = 0.1 MPa
m (cpd)/g 0.03724 0.04007 0.03956 0.03926 0.03966 0.03966 0.03940 0.03914
m (cotton)/g 0.00070 0.00069 0.00053 0.00060 0.00067 0.00066 0.00082 0.00053
m (Pt)/g 0.23219 0.23179 0.23183 0.23165 0.23202 0.23192 0.23224 0.23205
Ti/K 298.1521 298.0747 298.0738 298.0726 298.0726 298.0729 298.0738 298.0746
Tf/K 299.1001 299.1020 299.0830 299.0818 299.0872 299.0910 299.0867 299.0783
DTad/K 0.9171 0.9871 0.9707 0.9659 0.9780 0.9762 0.9708 0.9633
ei (cont.)/kJ K-1 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011 0.0011
ef (cont.)/kJ K-1 0.0012 0.0012 0.0012 0.0012 0.0012 0.0012 0.0012 0.0012
e calor (-DT)/kJ -1.1744 -1.2641 -1.2431 -1.2369 -1.2524 -1.2501 -1.2432 -1.2336
e cont (-DT)/kJ -0.0012 -0.0013 -0.0012 -0.0013 -0.0013 -0.0013 -0.0013 -0.0012
(-DUIBP)/kJ 1.1714 1.2612 1.2401 1.2340 1.2495 1.2472 1.2403 1.2306
(DUign)/kJ 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042 0.0042
DUR/kJ 0.0007 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008
(-mDcu°) (cotton)/kJ 0.0119 0.0117 0.0090 0.0102 0.0113 0.0111 0.0138 0.0089
(-mDcu°) (cpd)/kJ 1.1588 1.2487 1.2303 1.2230 1.2374 1.2353 1.2257 1.2209
(-Dcu°) (cpd)/kJ g-1 31.1171 31.1630 31.0996 31.1513 31.2002 31.1473 31.1091 31.1932
h-Dcu°(298.15 K) kJ g-1i = 31.1476 ± 0.0132
The symbols have the same meaning than Table 2

123
Formation of C3CA, 6MCC and 6M4C
Table 5 Standard molar energy and enthalpy of combustion and the
standard molar enthalpy of formation of the compounds at
T = 298.15 K y p° = 0.1 MPa
Dc Umo / Dc Hmo / Df Hmo /
kJ mol-1 kJ mol-1 kJ mol-1
C3CA (s) 4,174.4 ± 2.2 4,173.1 ± 2.2 619.5 ± 2.6
6MCC (s) 4,815.7 ± 1.7 4,815.7 ± 1.7 656.2 ± 2.2
6M4C (s) 5,051.7 ± 2.7 5,055.4 ± 2.7 308.9 ± 3.0
The standard energies of combustion of chromone-3-car-
boxylic acid, 6MCC, and 6M4C were determined with a
micro-combustion calorimeter, reaching a precision of
0.04 % using small quantities of the samples (about 40 mg).
Comparison between the reported formation enthalpy of
C3CA [10] and the value determined in the present work leads
to a difference of 6.8 kJ mol-1. Taking into account the
uncertainties associated to each value, one may conclude that
they are very close even when they were determined using
different techniques: macro-static bomb combustion and
semi-micro bomb combustion calorimetries.
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