Abstract
A noval anilino-pyrimidine fungicide, pyrimethanil butanedioic salt (C28H32N6O4), was synthesized by a chemical reaction of pyrimethanil and butanedioic acid. The low-temperature heat capacities of the compound were measured with an adiabatic calorimeter from 80 to 380 K. The thermodynamic function data relative to 298.15 K were calculated based on the heat capacity fitted curve. The thermal stability of the compound was investigated by TG and DSC. The TG curve shows that pyrimethanil butanedioic salt starts to sublimate at 455.1 K and totally changes into vapor when the temperature reaches 542.5 K with the maximal speed of weight loss at 536.8 K. The melting point, the molar enthalpy (Δfus H m), and entropy (Δfus S m) of fusion were determined from its DSC curves. The constant-volume energy of combustion (Δc U m) of pyrimethanil butanedioic salt was measured by an isoperibol oxygen-bomb combustion calorimeter at T = (298.15 ± 0.001) K. From the Hess thermochemical cycle, the standard molar enthalpy of formation was derived and determined to be Δf H om (pyrimethanil butanedioic salt)=−285.4 ± 5.5 kJ mol−1.
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Wang HF, Gong JY, Sun XH, Liu YF, Cheng XY. Synthesis of pyrimethanil salts and test of their fungicidal activities. Chin J Synth Chem. 2005;13(3):231–5.
Guan GY, Fukuoka S, Yamashita S, Yamamoto T, Taniguchi H, Nakazawa Y. Magnetic transition in dimerized radical cation salt of (BPDT-TTF)2ICl2 studied by heat capacity measurements. J Therm Anal Calorim. 2013;113:1197–201.
Atanasova L, Baikusheva-Dimitrova G. Heat capacity and thermodynamic properties of tellurites Yb2(TeO3)3, Dy2(TeO3)3 and Er2(TeO3)3. J Therm Anal Calorim. 2012;107:809–12.
Paukov IE, Kovalevskaya YA, Boldyreva EV. Low-temperature heat capacity of L- and DL-phenylglycines. J Therm Anal Calorim. 2012;108:1311–6.
Rawat D, Dash S. The standard molar enthalpy of formation of LnPO4(s) (Ln = La, Nd, Sm) by solution calorimetry. J Therm Anal Calorim. 2013;112:147–54.
Han XW, Zhou CR, Shi XH. Determination of specific heat capacity and standard molar combustion enthalpy of taurine by DSC. J Therm Anal Calorim. 2012;109:441–6.
Wang MH, Lei H, Hou ZX, Wang SH. Heat capacities and standard molar enthalpy of formation of pyrimethanil maleic salt and pyrimethanil fumaric salt. J Therm Anal Calorim. 2013;114:313–9.
Wang MH, Tan ZC, Sun XH, Liu YF, Wang HF, Sun LX, Zhang T. Heat capacity and thermodynamic properties of pyrimethanil myristic salt (C26H41N3O2). J Chem Thermodyn. 2004;36:477–82.
Sun XH, Liu YF, Tan ZC, Di YY, Wang HF, Wang MH. Heat capacity and enthalpy of fusion of pyrimethanil laurate (C24H37N3O2). J Chem Thermodyn. 2004;36:895–9.
Sun XH, Liu YF, Tan ZC, Jia YQ, Wang MH. Heat capacity and thermodynamic properties of crystalline pyrimethanil phenoxyacetate(C20H21N3O3). Chem J Chinese U. 2006;27(6):1109–12.
Wang MH, Tan ZC, Sun XH, Zhang HT, Liu BP, Sun LX, Zhang T. Determination of heat capacities and thermodynamic properties of 2-(chloromethylthio)benzothiazole by an adiabatic calorimeter. J Chem Eng Data. 2005;50(1):270–3.
Tan ZC, Shi Q, Liu BP, Zhang HT. A fully automated adiabatic calorimeter for heat capacity measurement between 80 and 400 K. J Therm Anal Calorim. 2008;92:367–74.
Archer DG. Thermodynamic properties of synthetic sapphire (α-Al2O3), standard reference material 720 and the effect of temperature-scale differences on thermodynamic properties. J Phys Chem Data. 1993;22:1441–53.
Höhne GWH, Hemminger WF, Flammersheim HJ. Differential Scanning Calorimetry. 2nd ed. New York: Springer-Verlag; 2003.
Chen JT, Di YY, Tan ZC, Zhang HT, Sun LX. Determination of standard molar enthalpy of formation for crystalline endo-tricyclo[5.2.1.02,6] decane by isoperibal oxygen-bomb combustion calorimeter. Chem Pap. 2005;59(4):225–9.
Silva ALR, Cimas Á. Ribeiro da Silva MDMC. Thermochemistry of 2-methylbenzoxazole and 2,5-dimethylbenzoxazole: an experimental and computational study. Struct Chem. 2013;24:1863–72.
Report of the CODATA task group on key values for thermodynamics. J Chem Thermodyn. 1978; 10: 903-906.
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The authors gratefully acknowledge the National Natural Science Foundation of China for financial support to this work under the NSFC Grant No. 51302175.
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Wang, M., Lei, H., Zhang, J. et al. Molar heat capacities and standard molar enthalpy of formation of pyrimethanil butanedioic salt. J Therm Anal Calorim 117, 1335–1340 (2014). https://doi.org/10.1007/s10973-014-3871-7
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DOI: https://doi.org/10.1007/s10973-014-3871-7