{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:51:44Z","timestamp":1760147504330,"version":"build-2065373602"},"reference-count":74,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,2,7]],"date-time":"2023-02-07T00:00:00Z","timestamp":1675728000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Fundac\u00e3o para a Ci\u00eancia e Tecnologia (FCT)","award":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"],"award-info":[{"award-number":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"]}]},{"name":"national funds","award":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"],"award-info":[{"award-number":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"]}]},{"name":"Faculty of Sciences, University of Porto","award":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"],"award-info":[{"award-number":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"]}]},{"name":"IMS\u2014Institute of Molecular Sciences","award":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"],"award-info":[{"award-number":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"]}]},{"name":"national funds through the FCT-I.P.","award":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"],"award-info":[{"award-number":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"]}]},{"name":"FCT","award":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"],"award-info":[{"award-number":["FCT\/MCTES (PIDDAC)","UIDB\/00081\/2020","LA\/P\/0056\/2020","UI\/BD\/152715\/2022"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This work reports an experimental study aiming to determine the thermodynamic properties of five chlorinated compounds with environmental impact. The vapor pressures of the crystalline phases of three isomers of dichlorobenzoic acid (2,4-, 2,5-, and 2,6-) and 2,6-dichlorobenzonitrile were measured at several temperatures using the Knudsen effusion technique. Another technique (a static method based on capacitance diaphragm manometers) allowed the measurement of the vapor pressures of both the crystalline and liquid phases of 2,4-dichlorobenzonitrile between 303.0 and 380.0 K. This latter technique also enabled the measurement of sublimation vapor pressures of 2,6-dichlorobenzonitrile over a larger range interval of temperatures, T = 328.7 and 391.8 K. The standard molar enthalpy, entropy, and Gibbs energy of sublimation (for all the compounds studied) and vaporization (for 2,4-dichlorobenzonitrile) were derived, at reference temperatures, from the experimental vapor pressure results. The temperatures and enthalpies of fusion and the isobaric heat capacities of the five crystalline-substituted benzenes were determined using differential scanning calorimetry. The contributions of the three substituents (-COOH, -CN, and -Cl) to the sublimation thermodynamic properties of the compounds studied were discussed.<\/jats:p>","DOI":"10.3390\/molecules28041590","type":"journal-article","created":{"date-parts":[[2023,2,8]],"date-time":"2023-02-08T01:32:05Z","timestamp":1675819925000},"page":"1590","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Phase Transitions Equilibria of Five Dichlorinated Substituted Benzenes"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5424-5674","authenticated-orcid":false,"given":"Ana R. R. P.","family":"Almeida","sequence":"first","affiliation":[{"name":"Research Centre in Chemistry (CIQUP), Institute of Molecular Sciences (IMS), Department of Chemistry and Biochemistry (DQB), Faculty of Sciences, University of Porto (FCUP), Rua do Campo Alegre, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0076-445X","authenticated-orcid":false,"given":"Bruno D. A.","family":"Pinheiro","sequence":"additional","affiliation":[{"name":"Research Centre in Chemistry (CIQUP), Institute of Molecular Sciences (IMS), Department of Chemistry and Biochemistry (DQB), Faculty of Sciences, University of Porto (FCUP), Rua do Campo Alegre, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2210-3559","authenticated-orcid":false,"given":"Manuel J. S.","family":"Monte","sequence":"additional","affiliation":[{"name":"Research Centre in Chemistry (CIQUP), Institute of Molecular Sciences (IMS), Department of Chemistry and Biochemistry (DQB), Faculty of Sciences, University of Porto (FCUP), Rua do Campo Alegre, 4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,7]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/j.jct.2018.10.025","article-title":"Thermodynamic properties of organic substances: Experiment, modeling, and technological applications","volume":"131","author":"Kabo","year":"2019","journal-title":"J. Chem. Thermodyn."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"4987","DOI":"10.1021\/acs.iecr.0c05356","article-title":"Industrial requirements for thermodynamic and transport properties: 2020","volume":"60","author":"Kontogeorgis","year":"2021","journal-title":"Ind. Eng. Chem. 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