Skip to main content

Energetic characterization of indanone derivatives involved in biomass degradation


The energetic study of 6-methyl-1-indanone, 6-methoxy-1-indanone and 5,6-dimethoxy-1-indanone has been developed using calorimetric techniques and a computational methodology. The enthalpies of combustion and of sublimation of these compounds were determined from, respectively, static-bomb combustion calorimetry and high-temperature Calvet microcalorimetry. From these experimental data, the gas-phase standard molar enthalpies of formation were derived. Also, the temperature and the enthalpy of fusion of each compound were obtained by differential scanning calorimetry. Additionally, the gas-phase standard molar enthalpies of formation of these compounds were obtained from high-level ab initio calculations, at the G3(MP2)//B3LYP level of theory. The computational approach of these three indanone derivatives allowed us to establish their molecular structures, the co-existence of two and four stable conformations for 6-methoxy-1-indanone and 5,6-dimethoxy-1-indanone, respectively. Furthermore, the energetic effects associated with the presence of one methyl group and one or two methoxy groups in the indanone structure were evaluated. These enthalpic increments were compared with the homologous substitutions in the benzene and naphthalene molecules.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3
Fig. 4


  1. Kohl T, Sapei E, Rocha IM, Galvao TL, Ribeiro da Silva MDMC, Ribeiro da Silva MAV. Modeling of fast pyrolysis of wood for prediction of bio-oil composition. In: Asia pacific confederation of chemical engineering congress 2015: APCChE 2015, incorporating CHEMECA. Engineers Australia; 2015. P. 2410.

  2. Rocha IM, Galvão TLP, Sapei E, Ribeiro da Silva MDMC, Ribeiro da Silva MAV. Levoglucosan: a calorimetric, thermodynamic, spectroscopic, and computational investigation. J Chem Eng Data. 2013;58:1813–21.

    Article  CAS  Google Scholar 

  3. Freitas VLS, Lima ACMO, Sapei E, Ribeiro da Silva MDMC. Comprehensive thermophysical and thermochemical studies of vanillyl alcohol. J Chem Thermodyn. 2016;102:287–92.

    Article  CAS  Google Scholar 

  4. Sabbah R, Xu-wu A, Chickos JS, Leitão MLP, Roux MV, Torres LA. Reference materials for calorimetry and differential thermal analysis. Thermochim Acta. 1999;331:193–204.

    Google Scholar 

  5. Gundry HA, Harrop D, Head AJ, Lewis GB. Thermodynamic properties of organic oxygen compounds 21. Enthalpies of combustion of benzoic acid, pentan-1-ol, octan-1-ol, and hexadecan-1-ol. J Chem Thermodyn. 1969;1:321–32.

    Article  CAS  Google Scholar 

  6. Ribeiro da Silva MDMC, Santos LMNBF, Silva ALR, Fernandes O, Acree WE Jr. Energetics of 6-methoxyquinoline and 6-methoxyquinoline N-oxide: the dissociation enthalpy of the (N–O) bond. J Chem Thermodyn. 2003;35:1093–100.

    Article  CAS  Google Scholar 

  7. Hubbard WN, Scott DW, Waddington G. Standard states and corrections for combustions in a bomb at constant volume. In: Rossini FD, editor. Experimental thermochemistry, vol. 1. New York: Interscience; 1956. p. 75–128.

    Google Scholar 

  8. Adedeji FA, Brown DLS, Connor JA, Leung WL, Paz-Andrade IM, Skinner HA. Thermochemistry of arene chromium tricarbonyls and the strenghts of arene-chromium bonds. J Organomet Chem. 1975;97:221–8.

    Article  CAS  Google Scholar 

  9. Santos LMNBF, Schröder B, Fernandes OOP, Ribeiro da Silva MAV. Measurement of enthalpies of sublimation by drop method in a Calvet type calorimeter: design and test of a new system. Thermochim Acta. 2004;415:15–20.

    Article  CAS  Google Scholar 

  10. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JAJ, Stratmann RE, Burant JC, et al. Gaussian03, revision C.01. Wallingford: Gaussian Inc.; 2004.

    Google Scholar 

  11. Baboul AG, Curtiss LA, Redfern PC, Raghavachari K. Gaussian-3 theory using density functional geometries and zero-point energies. J Chem Phys. 1999;110:7650–7.

    Article  CAS  Google Scholar 

  12. Rossini FD. Assignment of uncertainties to thermochemical data. In: Rossini FD, editor. Experimental thermochemistry, vol. 1. New York: Interscience; 1956. p. 297–325.

    Google Scholar 

  13. Olofson G. Assignment of uncertainties. In: Sunner S, Mansson M, editors. Combustion calorimetry, vol. 1. Oxford: Pergamon Press; 1979. p. 137–59.

    Chapter  Google Scholar 

  14. Cox JD, Wagman DD, Medvedev VA. CODATA key values for thermodynamics. New York: Hemisphere; 1979.

    Google Scholar 

  15. Irikura KK, Thermo PL. National institute of standards and technology; 2002.

  16. Merrick JP, Moran D, Radom L. An evaluation of harmonic vibrational frequency scale factors. J Phys Chem A. 2007;111:11683–700.

    Article  CAS  Google Scholar 

  17. Roux MV, Temprado M, Chickos JS, Nagano Y. Critically evaluated thermochemical properties of polycyclic aromatic hydrocarbons. J Phys Chem Ref Data. 2008;37:1855–996.

    Article  CAS  Google Scholar 

  18. Matos MAR, Miranda MS, Monte MJS, Santos LMNBF, Morais VMF, James S, Chickos JS, Umnahanant P, Liebman JF. Calorimetric and computational study of indanones. J Phys Chem A. 2007;111:11153–9.

    Article  CAS  Google Scholar 

  19. Speros DM, Rossini FD. Heats of combustion and formation of naphthalene, the two methylnaphthalenes, cis and trans decahydronaphthalene and related compounds. J Phys Chem. 1960;64:1723–7.

    Article  CAS  Google Scholar 

  20. Pedley JP. Thermochemical data and structures of organic compounds. College Station: Thermodynamics Research Centre; 1994.

    Google Scholar 

  21. Silva ALR, Freitas VLS, Ribeiro da Silva MDMC. Effects of methoxy and formyl substituents on the energetics and reactivity of α-naphthalenes: a calorimetric and computational study. Chemosphere. 2014;107:203–10.

    Article  CAS  Google Scholar 

  22. Matos MAR, Miranda MS, Morais VMF. Calorimetric and theoretical determination of standard enthalpies of formation of dimethoxy- and trimethoxybenzene isomers. J Phys Chem A. 2000;104:9260–5.

    Article  CAS  Google Scholar 

Download references


Thanks are due to Fundação para a Ciência e Tecnologia (FCT), Lisbon, Portugal, for the financial support to Project UID/QUI/0081/2013 and to FEDER through Program NORTE2020 for the financial support to Project POCI-01-0145-FEDER-006980 and to Project “Sustained Advanced Materials,” ref. NORTE-01-0145-FEDER-000028 (FCUP).

Author information

Authors and Affiliations


Corresponding author

Correspondence to Maria D. M. C. Ribeiro da Silva.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 676 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Silva, A.L.R., Lima, A.C.M.O. & Ribeiro da Silva, M.D.M.C. Energetic characterization of indanone derivatives involved in biomass degradation. J Therm Anal Calorim 134, 1267–1276 (2018).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI:


  • 6-R-1-indanone (R-methyl, methoxy)
  • 5,6-Dimethoxy-1-indanone
  • Enthalpy of formation
  • Enthalpy of sublimation
  • Enthalpy of fusion
  • G3(MP2)//B3LYP method