Abstract
A rapid estimation of vapor pressure and vaporization enthalpies of some disubstituted benzoic acids (2,4-dihydroxybenzoic acid (2,4-DHBA), 2,6-dihydroxybenzoic acid (2,6-DHBA), 3,4-dihydroxybenzoic acid (3,4-DHBA), 2,4-dinitrobenzoic acid (2,4-DNBA), 3,4-dinitrobenzoic acid (3,4-DNBA), 2,5-dibromobenzoic acid (2,5-DBBA), and 3,5-dibromobenzoic acid (3,5-DBBA)) was made using a simultaneous TG/DSC apparatus operating with aluminum open crucibles under inert atmosphere in both isothermal and non-isothermal mode. No evidence of thermal decomposition (in the form of endo or exothermic effect) was found during each experiment. Vapor pressure was obtained in the range from some tenth to some hundreds of Pa after calibration with benzoic acid. All operative conditions (sample mass, temperature rage, and purge gas flow) were carefully checked in order to obtain reliable results. Internal consistency of the results obtained was checked by comparing the sublimation enthalpy obtained by the sum of the vaporization enthalpies derived by the global NITG and ITG data, the melting enthalpies from DSC adjusted at 298.15 using the molar isobaric heat capacities of both solid and liquid estimated according to a group additivity approach and that obtained from the sublimation enthalpies determined by torsion effusion corrected at 298.15 K using the same approach. Finally, some comments concerning the relationship between energetics and structure (substituent effect) are also reported.
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References
Price DM, Hawkins M (1998) Thermochim Acta 315(1998):19–24
Price DM (2001) Thermochim Acta 367–368:253–262
Price DM (2001) J Therm Anal Calorim 64:315–322
Price DM, Hawkins M (1999) Thermochim Acta 329:73–76
Price DM, Bashir S, Derrick PR (1999) Thermochim Acta 327:167–171
Luo H, Baker GA, Dai S (2008) J Phys Chem B 112:10077–10081
Verevkin SP, Ralys R, Zaitsau DH, Emel’yanenko VN (2012) Thermochim Acta 538:55–62
Dollimore D (1999) Thermochim Acta 340:19–29
Elder JP (1997) J Therm Anal 49:897–905
Chatterjee K, Dollimore D, Alexander KS (2001) Int J Pharm 213:31–44
Chatterjee K, Dollimore D, Alexander KS (2001) J Therm Anal 63:629–639
Phang P, Dollimore D (1999) Proc NATAS Ann Conf Therm Anal Appl 27:598–601
Phang P, Dollimore D, Evans S (2000) Proc NATAS Ann Conf Therm Anal Appl 28:54–59
Burnham L, Dollimore D, Alexander KS (1999) Proc NATAS Ann Conf Therm Anal Appl 27:602–606
Wright SF, Alexander KS, Dollimore D (2001) Thermochim Acta 367:29–35
Chatterjee K, Dollimore D, Alexander KS (2001) Instrum Sci Technol 29:133–144
Gueckel W, Rittig FR, Synnatschke G (1974) Pestic Sci 5:393–400
Moelwyn-Hughes EA (1957) Physical chemistry. Pergamon Press, London
Mortensen EA, Eyring H (1960) J Phys Chem 64:846–849
Pieterse N, Focke WW (2003) Thermochim Acta 406:191–198
Chatterjee K, Dollimore D, Alexander KS (2002) Thermochim Acta 392–393:107–117
Månsson M, Sellers P, Stridh G, Sunner S (1977) J Chem Thermodyn 9:91–97
Lerdkanchanaporn S, Dollimore D (1998) Thermochim Acta 324:15–23
Barontini F, Cozzani V (2007) Thermochim Acta 460:15–21
Vecchio S (2006) J Therm Anal Calorim 84:271–278
Vecchio S (2007) J Therm Anal Calorim 87:79–83
Vecchio S (2010) Thermochim Acta 499:27–33
Vecchio S, Brunetti B (2011) Thermochim Acta 515:84–90
Vecchio S, Brunetti B (2009) J Chem Thermodyn 41:880–887
Vecchio S, Brunetti B (2013) Fluid Phase Equilib 338:148–154
Vecchio S, Brunetti B (2007) J Chem Eng Data 52:1585–1594
Vecchio S, Brunetti B (2005) J Chem Eng Data 50:666–672
Langmuir I (1913) Phys Rev 2:329–342
Chickos JS, Hesse DG, Liebman JF (1993) Struct Chem 4:261–269
Monte MJS, Goncalves MV, Ribeiro da Silva MDMC (2010) J Chem Eng Data 55:2246–2251
Plato C (1969) Anal Chem 41:330–336
Sabbah R, Xu-Wu A, Chickos JS, Planas Leitão ML, Roux MV, Torres LA (1999) Thermochim Acta 331:93–204
Brunetti B, Piacente V, Scardala P (2007) J Chem Eng Data 52:24–29
De Kruif CG, Blok JG (1982) J Chem Thermodyn 14:201–206
Stephenson RM, Malanowski S (1987) Handbook of the thermodynamics of organic compounds. Elsevier, New York, p 263
Focke WW (2003) J Therm Anal Cal 74:97–107
Monte MJS, Hillesheim DM (2001) J Chem Thermodyn 33:103–112
Ribeiro da Silva MAV, Monte MJS (1990) Thermochim Acta 171:169–183
Pinto SS, Diogo P, Guedes RC, Costa Gabral BJ, Minas de Piedade ME, Martinho Simões JA (2005) J Phys Chem A 109:9700–9708
Ribeiro da Silva MAV, Matos MAR, Monte MJS, Hillesheim DM, Marques MCPO, Vieira NFTG (1999) J Chem Thermodyn 31:1429–1441
Ribeiro da Silva MAV, Fonseca JMS, Carvalho RPBM, Monte MJS (2005) J Chem Thermodyn 37:271–279
Lima CFRAC, Gomes LR, Santos LMNBF (2007) J Phys Chem A 111:10598–10603
Ju K-S, Parales RE (2010) Microbiol Mol Biol Rev 74:250–272
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The author is indebted to Dr. Bruno Brunetti for his contribution in providing torsion–effusion experiments.
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This paper is devoted to Prof. Maria Victoria Roux in occasion of her 70th birthday.
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Vecchio, S. Thermogravimetric method for a rapid estimation of vapor pressure and vaporization enthalpies of disubstituted benzoic acids: an attempt to correlate vapor pressures and vaporization enthalpies with structure. Struct Chem 24, 1821–1827 (2013). https://doi.org/10.1007/s11224-013-0232-2
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DOI: https://doi.org/10.1007/s11224-013-0232-2