{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,31]],"date-time":"2025-12-31T18:20:41Z","timestamp":1767205241617,"version":"build-2238731810"},"reference-count":62,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2024,6,7]],"date-time":"2024-06-07T00:00:00Z","timestamp":1717718400000},"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","award":["UIDB\/00081\/2020"],"award-info":[{"award-number":["UIDB\/00081\/2020"]}]},{"name":"Fundac\u00e3o para a Ci\u00eancia e Tecnologia","award":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}]},{"name":"Fundac\u00e3o para a Ci\u00eancia e Tecnologia","award":["CEECIND\/03202\/2018"],"award-info":[{"award-number":["CEECIND\/03202\/2018"]}]},{"name":"Institute of Molecular Sciences","award":["UIDB\/00081\/2020"],"award-info":[{"award-number":["UIDB\/00081\/2020"]}]},{"name":"Institute of Molecular Sciences","award":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}]},{"name":"Institute of Molecular Sciences","award":["CEECIND\/03202\/2018"],"award-info":[{"award-number":["CEECIND\/03202\/2018"]}]},{"name":"FCT-I.P.","award":["UIDB\/00081\/2020"],"award-info":[{"award-number":["UIDB\/00081\/2020"]}]},{"name":"FCT-I.P.","award":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}]},{"name":"FCT-I.P.","award":["CEECIND\/03202\/2018"],"award-info":[{"award-number":["CEECIND\/03202\/2018"]}]},{"name":"FCT\/MCTES","award":["UIDB\/00081\/2020"],"award-info":[{"award-number":["UIDB\/00081\/2020"]}]},{"name":"FCT\/MCTES","award":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}]},{"name":"FCT\/MCTES","award":["CEECIND\/03202\/2018"],"award-info":[{"award-number":["CEECIND\/03202\/2018"]}]}],"content-domain":{"domain":["www.mdpi.com"],"crossmark-restriction":true},"short-container-title":["Molecules"],"abstract":"<jats:p>The need to transition from fossil fuels to renewables arises from factors such as depletion, price fluctuations, and environmental considerations. Lignocellulosic biomass, being abundant, and quickly renewable, and not interfering with food supplies, offers a standout alternative for chemical production. This paper explores the energetic characteristics of two derivatives of furfural\u2014a versatile chemical obtained from biomass with great potential for commercial sustainable chemical and fuel production. The standard (p\u00b0 = 0.1 MPa) molar enthalpies of formation of the liquids furfurylamine and 5-methylfurfurylamine were derived from the standard molar energies of combustion, determined in oxygen and at T = 298.15 K, by static bomb combustion calorimetry. Their standard molar enthalpies of vaporization were also determined at the same temperature using high-temperature Calvet microcalorimetry. By combining these data, the gas-phase enthalpies of formation at T = 298.15 K were calculated as \u2212(43.5 \u00b1 1.4) kJ\u00b7mol\u22121 for furfurylamine, and \u2212(81.2 \u00b1 1.7) kJ\u00b7mol\u22121 for 5-methylfurfurylamine. Furthermore, a theoretical analysis using G3 level calculations was performed, comparing the calculated enthalpies of formation with the experimental values to validate both results. This method has been successfully applied to similar molecules. The discussion looks into substituent effects in terms of stability and compares them with similar compounds.<\/jats:p>","DOI":"10.3390\/molecules29122729","type":"journal-article","created":{"date-parts":[[2024,6,7]],"date-time":"2024-06-07T11:56:48Z","timestamp":1717761408000},"page":"2729","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Thermochemical Research on Furfurylamine and 5-Methylfurfurylamine: Experimental and Computational Insights"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7158-2699","authenticated-orcid":false,"given":"Lu\u00edsa M. P. F.","family":"Amaral","sequence":"first","affiliation":[{"name":"LAQV\/REQUIMTE (Laborat\u00f3rio Associado para a Qu\u00edmica Verde), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, P-4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5424-5674","authenticated-orcid":false,"given":"Ana R. R. P.","family":"Almeida","sequence":"additional","affiliation":[{"name":"Research Centre in Chemistry (CIQUP), Institute of Molecular Sciences (IMS), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, P-4169-007 Porto, Portugal"}]},{"given":"Manuel A. V.","family":"Ribeiro da Silva","sequence":"additional","affiliation":[{"name":"Research Centre in Chemistry (CIQUP), Institute of Molecular Sciences (IMS), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, P-4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,7]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Gopalakrishnan, K., van Leeuwen, J., and Brown, R. (2012). Key issues in life cycle assessment of biofuels. Sustainable Bioenergy and Bioproducts. Green Energy and Technology, Springer.","DOI":"10.1007\/978-1-4471-2324-8"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"510","DOI":"10.1039\/D1GC03278J","article-title":"Furfural\u2014A versatile, biomass-derived platform chemical for the production of renewable chemicals","volume":"24","author":"Jaswal","year":"2022","journal-title":"Green Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1063\/1.4704200","article-title":"Biomass energy: Sustainable solution for greenhouse gas emission","volume":"1440","author":"Islama","year":"2012","journal-title":"AIP Conf. Proc."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Di, J., Li, Q., Ma, C., and He, Y.-C. (2023). An efficient and sustainable furfurylamine production from biomass-derived furfural by a robust mutant \u03c9-transaminase biocatalyst. Bioresour. Technol., 369.","DOI":"10.1016\/j.biortech.2022.128425"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1016\/j.biortech.2017.12.098","article-title":"Production of 5-hydroxymethylfurfural from starch-rich food waste catalyzed by sulfonated biochar","volume":"252","author":"Cao","year":"2018","journal-title":"Bioresour. Technol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1757","DOI":"10.1007\/s10098-020-01945-5","article-title":"The production of fuels and chemicals in the new world: Critical analysis of the choice between crude oil and biomass vis-\u00e0-vis sustainability and the environment","volume":"22","author":"Yadav","year":"2020","journal-title":"Clean Technol. Environ. Policy"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.gee.2022.07.003","article-title":"Catalytic conversion of lignocellulosic biomass into chemicals and fuels","volume":"8","author":"Deng","year":"2023","journal-title":"Green Energy Environ."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Yong, K.J., Wu, T.Y., Lee, C.B.T.L., Lee, Z.J., Liu, Q., Jahim, J.M., Zhou, Q., and Zhang, L. (2022). Furfural production from biomass residues: Current technologies, challenges and future prospects. Biomass Bioenergy, 161.","DOI":"10.1016\/j.biombioe.2022.106458"},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"He, W., He, Y.-C., and Ye, J. (2023). Efficient synthesis of furfurylamine from biomass via a hybrid strategy in an EaCl:Gly\u2013water medium. Front. Bioeng. Biotechnol., 11.","DOI":"10.3389\/fbioe.2023.1144787"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1039\/C6GC02241C","article-title":"Furfurylamines from biomass: Transaminase catalysed upgrading of furfurals","volume":"19","author":"Dunbabin","year":"2017","journal-title":"Green Chem."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Zhang, J., Yang, J., Li, X., Liu, H., Yao, X., Xia, C., and Huang, Z. (2023). Recent advances in the efficient synthesis of useful amines from biomass-based furan compounds and their derivatives over heterogeneous catalysts. Catalysts, 13.","DOI":"10.3390\/catal13030528"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.1016\/j.ijbiomac.2022.09.215","article-title":"Chemoenzymatic catalytic synthesis of furfurylamine from hemicellulose in biomasses","volume":"22","author":"Hea","year":"2022","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"102406","DOI":"10.1039\/C6RA22048G","article-title":"Synthesis and evaluation of polyaspartic acid\/furfurylamine graft copolymer as scale and corrosion inhibitor","volume":"6","author":"Shi","year":"2016","journal-title":"RSC Adv."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1039\/C9SC04460D","article-title":"Polyamide monomers via carbonate-promoted C\u2013H carboxylation of furfurylamine","volume":"11","author":"Lankenaua","year":"2020","journal-title":"Chem. Sci."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"720","DOI":"10.1007\/s10553-020-01087-w","article-title":"Furfural derivatives as fuel components","volume":"55","author":"Ershov","year":"2020","journal-title":"Chem. Technol. Fuels Oils"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1778","DOI":"10.1134\/S10704272150110063","article-title":"Antiknock properties of furfural derivatives","volume":"88","author":"Tarabanko","year":"2015","journal-title":"Russ. J. Appl. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1007\/s11030-013-9434-1","article-title":"Synthesis of novel isoquinolinone and 1,2-dihydroisoquinoline scaffolds via Ugi reaction and ring opening reaction of furans","volume":"17","author":"Ji","year":"2013","journal-title":"Mol. Divers."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1007\/s10934-022-01375-2","article-title":"Porous nitrogen-doped carbon supported MoO2\/Mo2C hybrid catalyst for efficient oxidative coupling of primary amines to imines","volume":"30","author":"Chen","year":"2023","journal-title":"J. Porous Mater."},{"key":"ref_19","first-page":"1106","article-title":"A new strategy for Pyrrolo[1,2-a][1,4]diazepine structure formation","volume":"7","author":"Stroganova","year":"2007","journal-title":"Synlett"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"116411","DOI":"10.1016\/j.poly.2023.116411","article-title":"Turn-ON\u2019 furfurylamine-based fluorescent sensor for Cd2+ ion detection and its application in real water samples","volume":"238","author":"Divyashree","year":"2023","journal-title":"Polyhedron"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.jct.2008.08.004","article-title":"Standard molar enthalpies of formation of 2-furancarbonitrile, 2-acetylfuran, and 3-furaldehyde","volume":"41","author":"Amaral","year":"2009","journal-title":"J. Chem. Thermodyn."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1016\/j.jct.2008.09.013","article-title":"Standard molar enthalpies of formation of some vinylfuran derivatives","volume":"41","author":"Amaral","year":"2009","journal-title":"J. Chem. Thermodyn."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1007\/s10973-009-0636-9","article-title":"Standard molar enthalpies of formation of some methylfuran derivatives","volume":"100","author":"Amaral","year":"2010","journal-title":"J. Therm. Anal. Calorim."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jct.2010.07.006","article-title":"Thermochemical study of 2,5-dimethyl-3-furancarboxilic acid, 4,5-dimethyl-2-furaldehyde and 3-acetyl-2,5-dimethylfuran","volume":"43","author":"Amaral","year":"2011","journal-title":"J. Chem. Thermodyn."},{"key":"ref_25","unstructured":"Rossini, F.D. (1956). Experimental Thermochemistry, Interscience. Chapter 14."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Sunner, S., and M\u00e5nsson, M. (1979). Combustion Calorimetry, Pergamon Press. Chapter 6.","DOI":"10.1016\/B978-0-08-020923-4.50026-4"},{"key":"ref_27","unstructured":"Cox, J.D., Wagman, D.D., and Medvedev, V.A. (1989). CODATA Key Values for Thermodynamics, Hemisphere Publishing Corp."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"11460","DOI":"10.1021\/jp992721u","article-title":"Structure and conformation of furfurylamine determined by gas-phase electron diffraction, microwave spectroscopy data, and ab initio molecular orbital calculations","volume":"103","author":"Hagen","year":"1999","journal-title":"J. Phys. Chem. A"},{"key":"ref_29","unstructured":"Levine, I.N. (2008). Physical Chemistry, McGraw-Hill Education."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"179536","DOI":"10.1016\/j.tca.2023.179536","article-title":"Enthalpy of formation and hydrogen bonded dimerization of furfurylamine: Experimental and computational study","volume":"725","author":"Lukyanova","year":"2023","journal-title":"Thermochim. Acta"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"8436","DOI":"10.1021\/ie050113x","article-title":"Estimation of the enthalpy of vaporization and the entropy of vaporization for pure organic compounds at 298.15 K and at normal boiling temperature by a group contribution method","volume":"44","author":"Kolska","year":"2005","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Naef, R., and Acree, W.E. (2017). Calculation of five thermodynamic molecular descriptors by means of a general computer algorithm based on the group-additivity method: Standard enthalpies of vaporization, sublimation and solvation, and entropy of fusion of ordinary organic molecules and total phase-change entropy of liquid crystals. Molecules, 22.","DOI":"10.20944\/preprints201705.0169.v1"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3295","DOI":"10.1039\/C9CE00435A","article-title":"In situ cryocrystallization and solid-state structures of furfural and some derivatives","volume":"21","author":"Seidel","year":"2019","journal-title":"CrystEngComm"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Pedley, J.B., Naylor, R.D., and Kirby, S.P. (1986). Thermochemical Data of Organic Compounds, Chapman and Hall.","DOI":"10.1007\/978-94-009-4099-4"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1016\/j.jct.2008.02.004","article-title":"Energetics of thiophenecarboxaldehydes and some of its alkyl derivatives","volume":"40","author":"Santos","year":"2008","journal-title":"J. Chem. Thermodyn."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1309","DOI":"10.1016\/j.jct.2008.03.008","article-title":"Experimental thermochemical study of the three methyl substituted 2-acetylthiophene isomers","volume":"40","author":"Santos","year":"2008","journal-title":"J. Chem. Thermodyn."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1923","DOI":"10.1007\/s11224-013-0272-7","article-title":"Dibenzofuran and methyldibenzofuran derivatives: Assessment of thermochemical data","volume":"24","author":"Freitas","year":"2013","journal-title":"Struct. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.theochem.2009.09.030","article-title":"A computational study on the thermochemistry of methylbenzo- and methyldibenzothiophenes","volume":"946","author":"Freitas","year":"2010","journal-title":"J. Mol. Struct Theochem"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.jct.2012.10.020","article-title":"Substituent effects in the thermochemistry of furans: A theoretical (CBS-QB3, CBS-APNO and G3) study","volume":"58","author":"Simmie","year":"2013","journal-title":"J. Chem. Thermodyn."},{"key":"ref_40","first-page":"163","article-title":"The construction, calibration and use of a new high precision static bomb calorimeter","volume":"26","author":"Pilcher","year":"1984","journal-title":"Rev. Port. Quim."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1149","DOI":"10.1016\/0021-9614(84)90187-3","article-title":"Enthalpies of combustion of 1,2-dihydroxybenzene and of six alkylsubstituted 1,2-dihydroxybenzenes","volume":"16","author":"Pilcher","year":"1984","journal-title":"J. Chem. Thermodyn."},{"key":"ref_42","unstructured":"(1995). Certificate of Analysis Standard Reference Material 39j Benzoic Acid Calorimetric Standard, NBS."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1776","DOI":"10.1039\/tf9605601776","article-title":"The heats of combustion of the four isomeric butyl alcohols","volume":"6","author":"Skinner","year":"1960","journal-title":"Trans. Faraday Soc."},{"key":"ref_44","unstructured":"Rossini, F.D. (1956). Calibration of calorimeters for reactions in a bomb at constant volume. Experimental Thermochemistry, Intercience. Chapter 3."},{"key":"ref_45","unstructured":"Wagman, D.D., Evans, W.H., Parker, V.B., Schumm, R.H., Halow, I., Bailey, S.M., Churney, K.L., and Nuttall, R.L. (1982). The NBS tables of chemical thermodynamic properties. Selected values for inorganic and C1 and C2 organic substances in SI units. J. Phys. Chem. Ref. Data, 11, Available online: https:\/\/srd.nist.gov\/JPCRD\/jpcrdS2Vol11.pdf."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"525","DOI":"10.6028\/jres.010.037","article-title":"Standard states for bomb calorimetry","volume":"10","author":"Washburn","year":"1933","journal-title":"J. Res. Nalt. Bur. Stand."},{"key":"ref_47","unstructured":"Rossini, F.D. (1956). Experimental Thermochemistry, Interscience. Chapter 5."},{"key":"ref_48","unstructured":"Aldrich Chemical Handbook of Fine Chemicals and Laboratory Equipment, Sigma-Aldrich Chemical Co.. 2008\u20132009."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1515\/pac-2015-0305","article-title":"Atomic weights of the elements 2013 (IUPAC Technical Report)","volume":"88","author":"Meija","year":"2016","journal-title":"Pure Appl. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/j.tca.2003.07.016","article-title":"Measurement of enthalpies of sublimation by drop method in a Calvet type calorimeter: Design and test of a new system","volume":"415","author":"Santos","year":"2004","journal-title":"Thermochim. Acta"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1016\/S0022-328X(00)89468-1","article-title":"Thermochemistry of arene chromium tricarbonyls and the strenghts of arene-chromium bonds","volume":"97","author":"Adedeji","year":"1975","journal-title":"J. Organomet. Chem."},{"key":"ref_52","unstructured":"(2023, May 23). NIST Computational Chemistry Comparison and Benchmark Database. 2013. NIST Standard Reference Database Number 101, Release 16a; Johnson, R.D., III, Ed.; NIST Chemistry Webbook. SRD 69, Available online: http:\/\/cccbdb.nist.gov\/vibscalejust.asp."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/S0040-6031(99)00009-X","article-title":"Reference materials for calorimetry and differential thermal analysis","volume":"331","author":"Sabbah","year":"1999","journal-title":"Thermochim. Acta"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"7764","DOI":"10.1063\/1.477422","article-title":"Gaussian-3 (G3) theory for molecules containing first and second-row atoms","volume":"109","author":"Curtiss","year":"1998","journal-title":"J. Chem. Phys."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"9017","DOI":"10.1021\/jp001972w","article-title":"A Theoretical determination of the heats of formation of furan, tetrahydrofuran, THF-2-yl, and THF-3-yl","volume":"104","author":"Feller","year":"2000","journal-title":"J. Phys. Chem. A"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"5128","DOI":"10.1021\/jp810315n","article-title":"Formation Enthalpies and Bond Dissociation Energies of Alkylfurans. The Strongest C\u2014X Bonds Known?","volume":"113","author":"Simmie","year":"2009","journal-title":"J. Phys. Chem. A"},{"key":"ref_57","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2009). Gaussian 09, Revision D.01, Gaussian, Inc."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1063\/1.2955570","article-title":"Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons","volume":"37","author":"Roux","year":"2008","journal-title":"J. Phys. Chem. Ref. Data"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1006\/jcht.1999.0587","article-title":"Thermochemical study of the ortho interactions in alkyl substituted anilines","volume":"32","author":"Verevkin","year":"2000","journal-title":"J. Chem. Thermodyn."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1016\/0040-6031(82)87105-0","article-title":"Thermodynamique de substances azotees. IX. Etude thermochimique de la benzamide. Comparaison des grandeurs energetiques liees a la structure de quelques amides et thioamides","volume":"58","author":"Gomez","year":"1982","journal-title":"Thermochim. Acta"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1063\/1.1420703","article-title":"Evaluated Enthalpies of Formation of the Stable Closed Shell C1 and C2 Chlorinated Hydrocarbons","volume":"31","author":"Manion","year":"2002","journal-title":"J. Phys. Chem. Ref. Data"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1023\/A:1022475115296","article-title":"Thermochemical Studies for Determination of the Standard Molar Enthalpies of Formation of Alkyl-Substituted Furans and Some Ethers","volume":"9","author":"Verevkin","year":"1998","journal-title":"Struct. Chem."}],"updated-by":[{"DOI":"10.3390\/molecules30132773","type":"correction","label":"Correction","source":"publisher","updated":{"date-parts":[[2024,6,7]],"date-time":"2024-06-07T00:00:00Z","timestamp":1717718400000}}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/12\/2729\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,8,3]],"date-time":"2025-08-03T14:32:47Z","timestamp":1754231567000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/12\/2729"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,7]]},"references-count":62,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2024,6]]}},"alternative-id":["molecules29122729"],"URL":"https:\/\/doi.org\/10.3390\/molecules29122729","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,7]]}}}