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Dibenzofuran and methyldibenzofuran derivatives: assessment of thermochemical data

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Abstract

Thermochemical data of dibenzofuran, a compound of considerable industrial and environmental significance, obtained from experimental calorimetric and computational techniques are reported in this work. The enthalpy of fusion, (19.4 ± 1.0) kJ mol−1, at the temperature of fusion, (355.52 ± 0.02) K, was determined by differential scanning calorimetry measurements of dibenzofuran. From the standard (p° = 0.1 MPa) molar enthalpies of formation of crystalline dibenzofuran, (−29.2 ± 3.8) kJ mol−1, and of sublimation, (84.5 ± 1.0) kJ mol−1, determined at T = 298.15 K by static bomb combustion calorimetry and by vacuum drop microcalorimetry, respectively, it was possible to calculate the enthalpy of formation of the gaseous compound, (55.0 ± 3.9) kJ mol−1, at the same temperature. The enthalpy of formation in the gaseous phase was also determined from G3(MP2)//B3LYP calculations. The same computational strategy was employed in the calculation of the standard molar enthalpies of formation, at T = 298.15 K, in the gas-phase, of single methylated derivatives of benzofuran and dibenzofuran.

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Acknowledgments

This work was mainly supported by Fundação para a Ciência e a Tecnologia (FCT), Lisbon, Portugal, and European Social Fund through strategic projects Pest-C/QUI/UI0081/2011 and Pest-C/CTM/LA0011/2011 awarded to CIQUP and CICECO, respectively. VLSF thanks FCT for Ph.D. research Grant SFRH/BD/41672/2007 and for the post-doctoral Grant SFRH/BPD/78552/2011. JRBG holds a Ciência 2007 position of the Portuguese Ministry of Science.

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Authors and Affiliations

  1. Centro de Investigação em Química, Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, Rua do Campo Alegre, 687, 4169-007, Porto, Portugal

    Vera L. S. Freitas & Maria D. M. C. Ribeiro da Silva

  2. CICECO, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193, Aveiro, Portugal

    José R. B. Gomes

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  1. Vera L. S. Freitas
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  2. José R. B. Gomes
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  3. Maria D. M. C. Ribeiro da Silva
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Correspondence to Maria D. M. C. Ribeiro da Silva.

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Special Issue in honor of Prof. Maria Victoria Roux.

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Supporting Information

Table S1 with the standard (p° = 0.1 MPa) molar heat capacities in the gaseous phase for dibenzofuran, determined by B3LYP/6-31G(d) calculations; Table S2 with the typical combustion results and standard (p° = 0.1 MPa) massic energy of combustion of dibenzofuran, at T = 298.15 K, and Table S3 with the G3(MP2)//B3LYP absolute enthalpies and the experimental gas-phase standard (p° = 0.1 MPa) molar enthalpies of formation, at T = 298.15 K, for dibenzofuran, for the methyl derivatives of benzofuran and dibenzofuran and for all the auxiliary species considered in the working reactions 5–19 (DOC 86 kb)

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Freitas, V.L.S., Gomes, J.R.B. & Ribeiro da Silva, M.D.M.C. Dibenzofuran and methyldibenzofuran derivatives: assessment of thermochemical data. Struct Chem 24, 1923–1933 (2013). https://doi.org/10.1007/s11224-013-0272-7

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