Thermodynamics Properties of 1,1-Carbonyldiimidazole (CDI) and 4-Imidazole Acrylic Acid, Obtained by DSC and Combustion Calorimetry

Authors

  • Baudelio Campos Universidad de Guadalajara
  • José María del Toro Jauregui Universidad de Guadalajara
  • Carmen Salomón Universidad de Guadalajara
  • Eulogio Orozco-Guareño Universidad de Guadalajara

DOI:

https://doi.org/10.29356/jmcs.v64i4.1193

Keywords:

Imidazole, enthalpy of formation, melting poing, calorimetry, CDI

Abstract

Abstract. In this work, thermodynamic properties of 1,1-carbonyldiimidazole (CDI) and 4-imidazole acrylic are reported. The melting temperature, the enthalpy of fusion and the heat capacity of the compounds were determined by differential scanning calorimetry. The standard molar energy of combustion of both compounds were determined by static-bomb combustion calorimetry and the standard molar enthalpy of formation in the crystalline phase, at T = 298.15 K, was derived and evaluated for the two imidazole derivatives studied. The energetic influence of the acrylic group on the imidazole ring in each of the properties obtained is analyzed and compared with the existing results in the literature.

Resumen. Se presentan las propiedades termodinámicas del 1,1-carbonildiimidazol (CDI) y el 4-imidazol acrílico. La temperatura de fusión, la entalpía de fusión y la capacidad calorífica de los compuestos se determinaron mediante calorimetría diferencial de barrido. La energía molar estándar de la combustión de ambos compuestos se determinó mediante calorimetría de combustión en bomba estática y la entalpía de formación en fase cristalina, a T= 298.15, fue derivada y evaluada para los dos compuestos derivados del imidazol. La influencia energética del grupo acrílico sobre el anillo de imidazol en cada una de las propiedades obtenidas se analiza y compara con los resultados existentes en la literatura.

Downloads

Download data is not yet available.

Author Biographies

Baudelio Campos, Universidad de Guadalajara

Laboratorio de Fisicoquímica-Departamento de Química, Centro Universitario de Ciencias Exactas e Ingenierías

José María del Toro Jauregui, Universidad de Guadalajara

Laboratorio de Fisicoquímica-Departamento de Química, Centro Universitario de Ciencias Exactas e Ingenierías

Carmen Salomón, Universidad de Guadalajara

Laboratorio de Fisicoquímica-Departamento de Química, Centro Universitario de Ciencias Exactas e Ingenierías

Eulogio Orozco-Guareño, Universidad de Guadalajara

Laboratorio de Fisicoquímica-Departamento de Química, Centro Universitario de Ciencias Exactas e Ingenierías

References

L. Wiseman, J. G. Lombardino, and E. H. Wiseman, “Preparation and Antiinflammatory Activity of Some Nonacidic Trisubstituted Imidazoles,” J. Med. Chem., vol. 17, no. 15, pp. 1182–1188, 1974.

R. J. Sundberg and R. B. Martin, “Interactions of Histidine and Other Imidazole Derivatives with Transition Metal Ions in Chemical and Biological Systems,” Chem. Rev., vol. 74, pp. 471–517, 1973.

K. Shalini, P. K. Sharma, and N. Kumar, “Imidazole and its biological activities : A review,” Chem. Sin., vol. 1, pp. 36–47, 2010.

A. S. Suvarna, “Imidazole and its derivatives and Importance in the Synthesis of Pharmaceuticals : A Review,” J. Chem. Sci., vol. 5, no. 10, pp. 67–72, 2015.

A. Verma, S. Joshi, and D. Singh, “Imidazole : Having Versatile Biological Activities,” J. Chem., vol. 2013, pp. 1–12, 2013.

J. Fortún Abete, “No Title,” Medicine (Baltimore)., vol. 7, no. 91, pp. 133–140, 1998.

N. K. Gibbs and M. Norval, “Recent advances in urocanic acid photochemistry , photobiology and photoimmunology,” Photochem. Photobiol. Sci., vol. 7, pp. 655–667, 2008.

I. R. Scott, “Factors controlling the expressed activity of histidine ammonia-lyase in the epidermis and the resulting accumulation of urocanic acid,” Biochem. J., vol. 194, pp. 829–838, 1981.

K. M. Hanson, B. Li, and J. D. Simon, “A Spectroscopic Study of the Epidermal Ultraviolet Chromophore trans -Urocanic Acid,” J. Am. Chem. Soc., vol. 119, pp. 2715–2721, 1997.

T. Mohammad, H. Morrison, and H. Hogenesch, “Invited Review Urocanic Acid Photochemistry and Photobiology,” vol. 69, no. 2, 1999.

A. T. Using and A. L. Weber, “Aqueous synthesis of peptide thioesters from amino acids and a thiol using 1,1 -carbonyldiimidazole,” Orig Life Evol Biosph, vol. 35, pp. 421–422, 2005.

C. Plato, “Differential Scanning Calorimetry as a General Method for Determining Purity and Heat of Fusion of High- Purity Organic Chemicals,” Anal. Chem., vol. 44, no. 8, pp. 1531–1534, 1972.

J. Morales, G. Günther, and A. L. Zanocco, “Rapid and Simple HPLC Method for the Simultaneous Determination of Urocanic Acid Isomers in Human Skin,” Anal. Lett., vol. 46, no. October 2013, pp. 37–41, 2012.

R. Sabbah, A. Xu-wu, J. S. Chickos, M. L. Planas Leitao, M. V. Roux, and L. A. Torres, “Reference materials for calorimetry and differential thermal analysis,” Thermochim. Acta, vol. 331, pp. 93–204, 1999.

G. Höne, H. Hemminger, and H.-J. Flammersheim, Differential Scanning Calorimetry An Introduction for Practitioners, 1st ed. New York, 1996.

J. B. Campos, A. J. Martinez-Gómez, and E. Orozco-Guareno, “Design and building of an isoperibolic calorimeter: Measurements of enthalpy of formation for derivatives of glycidol,” Meas. Sci. Technol., vol. 30, no. 3, pp. 1–14, 2019.

E. J. Prosen, “Combustion in a Bomb of Compounds Containing Carbon, Hydrogen, Oxygen, and Nitrogen,” in Experimental Thermochemistry Measurement of Heats of Reaction, 1st ed., New York: Interscience Publishers Inc., 1956, p. 141.

CODATA, “CODATA recommended key values for thermodynamics. Report of the CODATA Task Gropu on key values for thermodynamics.,” J. Chem. Thermodyn., vol. 10, pp. 903–906, 1978.

W. D. Good and N. K. Smith, “Enthalpies of combustion of toluene, benzene, cyclohexane, cyclohexene, methylcydopentane, 1-methylcyclopentene, and n-hexane,” J. Chem. Eng. Data, vol. 14, no. 1, pp. 102–106, 1969.

J. Meija et al., “Atomic weights of the elements 2013 (IUPAC Technical Report),” Pure Appl. Chem., vol. 88, no. 3, pp. 265–291, 2016.

E. W. Washburn, “Standard States for bomb Calorimetry,” Bur. Stand. J. Res., vol. 10, no. 4, pp. 525–558, 1933.

Additional Files

Published

2020-10-01

Issue

Section

Regular Articles