{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,13]],"date-time":"2026-02-13T05:06:40Z","timestamp":1770959200971,"version":"3.50.1"},"reference-count":37,"publisher":"Springer Science and Business Media LLC","issue":"9","license":[{"start":{"date-parts":[[2024,5,3]],"date-time":"2024-05-03T00:00:00Z","timestamp":1714694400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2024,5,3]],"date-time":"2024-05-03T00:00:00Z","timestamp":1714694400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100006752","name":"Universidade do Porto","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100006752","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["J Therm Anal Calorim"],"published-print":{"date-parts":[[2025,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n          <jats:p>The present work is focused on determining the enthalpy of formation of several derivatives of amino-1,2,4-triazoles. Experimentally, the enthalpies of formation of the crystalline phase and the enthalpies of sublimation of 3-amino- and 3,5-diamino-1<jats:italic>H<\/jats:italic>-1,2,4-triazole were derived, respectively, from static-bomb combustion calorimetry and Calvet microcalorimetry or Knudsen effusion measurements. For 4-amino-4<jats:italic>H<\/jats:italic>-1,2,4-triazole, only the enthalpy of sublimation was measured. Gas-phase standard molar enthalpies of formation were also estimated using theoretical calculations performed with the G3(MP2) composite approach. The very good agreement of these estimates with the experimental results, support the extension of this study to the estimate of this property for the remaining compounds not studied experimentally. The results obtained are interpreted in terms of structural contributions.<\/jats:p>","DOI":"10.1007\/s10973-024-13161-0","type":"journal-article","created":{"date-parts":[[2024,5,3]],"date-time":"2024-05-03T08:01:55Z","timestamp":1714723315000},"page":"6899-6907","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Thermochemistry of amino-1,2,4-triazole derivatives"],"prefix":"10.1007","volume":"150","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7158-2699","authenticated-orcid":false,"given":"Lu\u00edsa M. P. F.","family":"Amaral","sequence":"first","affiliation":[]},{"given":"T\u00e2nia M. T.","family":"Carvalho","sequence":"additional","affiliation":[]},{"given":"Maria D. M. C. Ribeiro","family":"da Silva","sequence":"additional","affiliation":[]}],"member":"297","published-online":{"date-parts":[[2024,5,3]]},"reference":[{"key":"13161_CR1","doi-asserted-by":"publisher","first-page":"2732","DOI":"10.1007\/s00044-015-1322-z","volume":"24","author":"M Aouali","year":"2015","unstructured":"Aouali M, Mhalla D, Allouche F, Kaim LE, Tounsi S, Trigui M, Chabchoub F. Synthesis, antimicrobial and antioxidant activities of imidazotriazoles and new multicomponent reaction toward 5-amino-1-phenyl[1,2,4]triazole derivatives. Med Chem Res. 2015;24:2732\u201341. https:\/\/doi.org\/10.1007\/s00044-015-1322-z.","journal-title":"Med Chem Res"},{"issue":"4","key":"13161_CR2","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0122781","volume":"10","author":"Y Jing","year":"2015","unstructured":"Jing Y, Wu K, Liu J, Ai Q, Ge P, Dai J, Jiang R, Zhou D, Che Q, Wan J, Zhang L. Aminotriazole alleviates acetaminophen poisoning via downregulating P450 2E1 and suppressing inflammation. PLoS ONE. 2015;10(4): e0122781. https:\/\/doi.org\/10.1371\/journal.pone.0122781.","journal-title":"PLoS ONE"},{"key":"13161_CR3","doi-asserted-by":"publisher","first-page":"1186","DOI":"10.1039\/C5MD00185D","volume":"6","author":"TV Serebryanskaya","year":"2015","unstructured":"Serebryanskaya TV, Zolotarev AA, Ott I. A novel aminotriazole-based NHC complex for the design of gold(I) anti-cancer agents: synthesis and biological evaluation. Med Chem Commun. 2015;6:1186\u20139. https:\/\/doi.org\/10.1039\/C5MD00185D.","journal-title":"Med Chem Commun"},{"key":"13161_CR4","doi-asserted-by":"publisher","first-page":"5","DOI":"10.14805\/jphchem.2014.art4","volume":"1","author":"U Kulandaivelu","year":"2014","unstructured":"Kulandaivelu U, Chawada B, Boyapati S, Reddy AR. Synthesis antimicrobial and anticancer activity of 1-[(arylalkylidene)amino]-3-(4H\u20131,2,4-Triazol-4-yl)thiourea. J Pharm Chem. 2014;1:5\u20139.","journal-title":"J Pharm Chem"},{"key":"13161_CR5","doi-asserted-by":"publisher","first-page":"403","DOI":"10.1002\/ps.2780310402","volume":"31","author":"GS Basarab","year":"1991","unstructured":"Basarab GS, Pifferitti M, Bolinski MM. The chemistry and biological activity of a new class of azole fungicides: 1-amino-1,2,4-triazoles. Pestic Sci. 1991;31:403\u201317. https:\/\/doi.org\/10.1002\/ps.2780310402.","journal-title":"Pestic Sci"},{"key":"13161_CR6","doi-asserted-by":"publisher","first-page":"5091","DOI":"10.5958\/0974-360X.2019.00882.5","volume":"12","author":"S Sahoo","year":"2019","unstructured":"Sahoo S, Sindhu KN, Sreeveena K. The significance of 1, 2, 4 -triazoles in agriculture science: a review. Res J Pharm Technol. 2019;12:5091\u2013191. https:\/\/doi.org\/10.5958\/0974-360X.2019.00882.5.","journal-title":"Res J Pharm Technol"},{"key":"13161_CR7","doi-asserted-by":"publisher","first-page":"394","DOI":"10.2174\/1570193X19666220331155015","volume":"20","author":"V Nazarov","year":"2023","unstructured":"Nazarov V, Miroshnichenko D, Oleksandra I, Serhiy P, Bohdan K. State of the art in industrial application of amino-1,2,4-triazoles. Mini-Rev Org Chem. 2023;20:394\u2013402. https:\/\/doi.org\/10.2174\/1570193X19666220331155015.","journal-title":"Mini-Rev Org Chem"},{"key":"13161_CR8","doi-asserted-by":"publisher","first-page":"174","DOI":"10.1002\/prep.200300002","volume":"28","author":"G Drake","year":"2003","unstructured":"Drake G, Hawkins T, Brand A, Hall L, Mckay M, Vij A, Ismail I. Energetic, low-melting salts of simple heterocycles. Propellants, Explos Pyrotech. 2003;28:174\u201380. https:\/\/doi.org\/10.1002\/prep.200300002.","journal-title":"Propellants, Explos Pyrotech"},{"key":"13161_CR9","volume-title":"High Energy Density Materials","author":"RP Singh","year":"2007","unstructured":"Singh RP, Gao H, Meshri DT, Shreeve JM. Nitrogen-Rich Heterocycles. In: Klap\u00f6tke TM, editor. High Energy Density Materials. Heidelberg: Structure and Bonding, Springer, Berlin; 2007."},{"key":"13161_CR10","doi-asserted-by":"publisher","first-page":"321","DOI":"10.1016\/0021-9614(69)90051-2","volume":"1","author":"HA Gundry","year":"1969","unstructured":"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\u201332. https:\/\/doi.org\/10.1016\/0021-9614(69)90051-2.","journal-title":"J Chem Thermodyn"},{"key":"13161_CR11","doi-asserted-by":"publisher","first-page":"373","DOI":"10.1016\/0021-9614(84)90175-7","volume":"16","author":"J Bickerton","year":"1984","unstructured":"Bickerton J, Pilcher G, Al-Takhin G. Enthalpies of combustion of the three aminopyridines and the three cyanopyridines. J Chem Thermodyn. 1984;16:373\u20138. https:\/\/doi.org\/10.1016\/0021-9614(84)90175-7.","journal-title":"J Chem Thermodyn"},{"key":"13161_CR12","doi-asserted-by":"publisher","first-page":"1093","DOI":"10.1016\/S0021-9614(03)00052-1","volume":"35","author":"MDMC da Ribeiro Silva","year":"2003","unstructured":"da Ribeiro 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\u2013O) bond. J Chem Thermodyn. 2003;35:1093\u2013100. https:\/\/doi.org\/10.1016\/S0021-9614(03)00052-1.","journal-title":"J Chem Thermodyn"},{"key":"13161_CR13","unstructured":"Certificate of Analysis Standard Reference Material 39j Benzoic Acid Calorimetric Standard. Washington, DC: NBS, 1995."},{"key":"13161_CR14","volume-title":"Experimental Thermochemistry","author":"J Copps","year":"1956","unstructured":"Copps J, Jessup RS, Van Nes K. Calibration of calorimeters for reactions in a bomb at constant volume. In: Rossini FD, editor. Experimental Thermochemistry. New York: Interscience; 1956."},{"key":"13161_CR15","doi-asserted-by":"publisher","first-page":"525","DOI":"10.6028\/jres.010.037","volume":"10","author":"EW Washburn","year":"1933","unstructured":"Washburn EW. Standard states for bomb calorimetry. J Res Nalt Bur Stand. 1933;10:525\u201358.","journal-title":"J Res Nalt Bur Stand."},{"key":"13161_CR16","volume-title":"Experimental Thermochemistry","author":"WN Hubbard","year":"1956","unstructured":"Hubbard WN, Scott DW, Waddington G. Standard states and corrections for combustions in a bomb at constant volume. In: Rossini FD, editor. Experimental Thermochemistry. New York: Interscience; 1956."},{"key":"13161_CR17","volume-title":"Thermophysical properties of chemicals and hydrocarbons","year":"2008","unstructured":"Yaws CL, editor. Thermophysical properties of chemicals and hydrocarbons. New York: William Andrew Inc.; 2008."},{"key":"13161_CR18","unstructured":"Aldrich, Chemical handbook of fine chemicals and laboratory equipment, the Sigma-Aldrich Chemical Co. Gillingham, UK."},{"key":"13161_CR19","doi-asserted-by":"publisher","first-page":"265","DOI":"10.1515\/pac-2015-0305","volume":"88","author":"J Meija","year":"2016","unstructured":"Meija J, Coplen TB, Berglund M, Brand WA, De Bi\u00e8vre P, Gr\u00f6ning M, Holden NE, Irrgeher J, Loss RD, Walczyk T, Prohaska T. Atomic weights of the elements 2013 (IUPAC Technical Report). Pure Appl Chem. 2016;88:265\u201391. https:\/\/doi.org\/10.1515\/pac-2015-0305.","journal-title":"Pure Appl Chem"},{"key":"13161_CR20","doi-asserted-by":"publisher","first-page":"221","DOI":"10.1016\/S0022-328X(00)89468-1","volume":"97","author":"FA Adedeji","year":"1975","unstructured":"Adedeji FA, Brown DLS, Connor JA, Leung M, Paz-Andrade MI, Skinner HA. Thermochemistry of arene chromium tricarbonyls and the strengths of arene-chromium bonds. J Orgnomet Chem. 1975;97:221\u20138. https:\/\/doi.org\/10.1016\/S0022-328X(00)89468-1.","journal-title":"J Orgnomet Chem"},{"key":"13161_CR21","doi-asserted-by":"publisher","first-page":"15","DOI":"10.1016\/j.tca.2003.07.016","volume":"415","author":"LMNBF Santos","year":"2004","unstructured":"Santos LMNBF, Schr\u00f6der B, Fernandes OOP, da Ribeiro 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\u201320. https:\/\/doi.org\/10.1016\/j.tca.2003.07.016.","journal-title":"Thermochim Acta"},{"key":"13161_CR22","doi-asserted-by":"publisher","first-page":"778","DOI":"10.1016\/j.jct.2005.08.013","volume":"38","author":"MAV da Ribeiro Silva","year":"2006","unstructured":"da Ribeiro Silva MAV, Monte MJS, Santos LMNBF. The design, construction, and testing of a new Knudsen effusion apparatus. J Chem Thermodyn. 2006;38:778\u201387. https:\/\/doi.org\/10.1016\/j.jct.2005.08.013.","journal-title":"J Chem Thermodyn"},{"key":"13161_CR23","doi-asserted-by":"publisher","first-page":"4703","DOI":"10.1063\/1.478385","volume":"110","author":"LA Curtiss","year":"1999","unstructured":"Curtiss LA, Redfern PC, Raghavachari K, Rassolov V. Pople JA Gaussian-3 theory using reduced M\u00f8ller\u2013Plesset order. J Chem Phys. 1999;110:4703\u20139. https:\/\/doi.org\/10.1063\/1.478385.","journal-title":"J Chem Phys"},{"key":"13161_CR24","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540070314","volume-title":"Ab initio molecular orbital theory","author":"WJ Hehre","year":"1987","unstructured":"Hehre WJ, Radom L, Pople JA, Schleyer PR. Ab initio molecular orbital theory. New York: Wiley; 1987. https:\/\/doi.org\/10.1002\/jcc.540070314."},{"key":"13161_CR25","doi-asserted-by":"publisher","first-page":"269","DOI":"10.1002\/qua.560200829","volume":"15","author":"JA People","year":"1981","unstructured":"People JA, Schlegel HB, Krishnan R, Defrees DJ, Binkley JS, Frisch MJ, Whiteside RA, Hout RF, Hehre WJ. Molecular orbital studies of vibrational frequencies. Int J Quan Chem Symp. 1981;15:269\u201373. https:\/\/doi.org\/10.1002\/qua.560200829.","journal-title":"Int J Quan Chem Symp"},{"key":"13161_CR26","doi-asserted-by":"publisher","first-page":"16502","DOI":"10.1021\/jp960976r","volume":"100","author":"PA Scott","year":"1996","unstructured":"Scott PA, Radom L. Harmonic vibrational frequencies: an evaluation of Hartree\u2212Fock, M\u00f8ller\u2212Plesset, quadratic configuration interaction, Density functional theory, and semiempirical scale factors. J Phys Chem. 1996;100:16502\u201313. https:\/\/doi.org\/10.1021\/jp960976r.","journal-title":"J Phys Chem"},{"key":"13161_CR27","unstructured":"Irikura KK. THERMO.PL, National Institute of Standards and Technology, 2002 (http:\/\/www.cstl.nist.gov\/div838\/group06\/irikura\/prog\/thermo.html)."},{"key":"13161_CR28","volume-title":"Gaussian 03, Revision C.01","author":"MJ Frisch","year":"2004","unstructured":"Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM. Gaussian 03, Revision C.01. Wallingford: Gaussian Inc; 2004."},{"key":"13161_CR29","volume-title":"CODATA key values for thermodynamics","author":"JD Cox","year":"1984","unstructured":"Cox JD, Wagman DD, Medvedev VA. CODATA key values for thermodynamics. New York: Hemisphere Publishing Corp; 1984."},{"key":"13161_CR30","volume-title":"Experimental thermochemistry","author":"FD Rossini","year":"1956","unstructured":"Rossini FD. Assignment of uncertainties. In: Rossini FD, editor. Experimental thermochemistry, vol. 1. New York: Interscience; 1956."},{"key":"13161_CR31","volume-title":"Combustion Calorimetry","author":"G Olofson","year":"1979","unstructured":"Olofson G. Assignment of uncertainties. In: Sunner S, M\u00e5nsson M, editors. Combustion Calorimetry. Oxford: Pergamon Press; 1979."},{"key":"13161_CR32","unstructured":"NIST Chemistry WebBook. http:\/\/webbook.nist.gov, (Accessed 1 November 2023)."},{"key":"13161_CR33","doi-asserted-by":"publisher","first-page":"271","DOI":"10.1007\/BF00673701","volume":"4","author":"JS Chickos","year":"1993","unstructured":"Chickos JS, Hosseini S, Hesse DG, Liebman JF. Heat capacity corrections to a standard state: a comparison of new and some literature methods for organic liquids and solids. Struct Chem. 1993;4:271\u20138. https:\/\/doi.org\/10.1007\/BF00673701.","journal-title":"Struct Chem"},{"key":"13161_CR34","doi-asserted-by":"publisher","first-page":"419","DOI":"10.1021\/je9004036","volume":"55","author":"MJS Monte","year":"2010","unstructured":"Monte MJS, Almeida ARRP, Matos MAR. Thermodynamic study on the sublimation of five aminomethoxybenzoic acids. J Chem Eng Data. 2010;55:419\u201323. https:\/\/doi.org\/10.1021\/je9004036.","journal-title":"J Chem Eng Data"},{"key":"13161_CR35","volume-title":"Thermodynamics Research Center, College Station","author":"JB Pedley","year":"1994","unstructured":"Pedley JB. Thermochemical data and structures of organic compounds. In: Thermodynamics Research Center, College Station. USA: CRC Press; 1994."},{"key":"13161_CR36","doi-asserted-by":"publisher","first-page":"198","DOI":"10.1016\/j.cplett.2009.10.082","volume":"483","author":"A Lesar","year":"2009","unstructured":"Lesar A, Milo\u0161ev I. Density functional study of the corrosion inhibition properties of 1,2,4-triazole and its amino derivatives. Chem Phys Letters. 2009;483:198\u2013203. https:\/\/doi.org\/10.1016\/j.cplett.2009.10.082.","journal-title":"Chem Phys Letters"},{"issue":"1","key":"13161_CR37","doi-asserted-by":"publisher","first-page":"347","DOI":"10.1016\/j.saa.2010.10.019","volume":"78","author":"L Guennoun","year":"2011","unstructured":"Guennoun L, El Jastimi J, Gu\u00e9dira F, Marakchi K, Kabbaj OK, El Hajji A, Zaydoun S. Molecular geometry and vibrational studies of 3,5-diamino-1,2,4-triazole using quantum chemical calculations and FT-IR and FT-Raman spectroscopies. Spectrochim Acta Part A Mol Biomol Spectrosc. 2011;78(1):347\u201353. https:\/\/doi.org\/10.1016\/j.saa.2010.10.019.","journal-title":"Spectrochim Acta Part A Mol Biomol Spectrosc"}],"container-title":["Journal of Thermal Analysis and Calorimetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s10973-024-13161-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1007\/s10973-024-13161-0\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s10973-024-13161-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,9,5]],"date-time":"2025-09-05T19:12:02Z","timestamp":1757099522000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1007\/s10973-024-13161-0"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,5,3]]},"references-count":37,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2025,5]]}},"alternative-id":["13161"],"URL":"https:\/\/doi.org\/10.1007\/s10973-024-13161-0","relation":{},"ISSN":["1388-6150","1588-2926"],"issn-type":[{"value":"1388-6150","type":"print"},{"value":"1588-2926","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,5,3]]},"assertion":[{"value":"2 February 2024","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"31 March 2024","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"3 May 2024","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"The authors declare that they have no conflict of interest.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Conflict of interest"}},{"value":"The measurements and experimental techniques used are standard procedures within the field, and the properties investigated necessitate a detailed and specific description of methods, procedures, and experimental uncertainties. As such, it is inevitable that there will be some level of overlap with previously published works.","order":3,"name":"Ethics","group":{"name":"EthicsHeading","label":"Ethical approval"}}]}}