{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:11:54Z","timestamp":1760105514013,"version":"build-2065373602"},"reference-count":31,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2024,1,2]],"date-time":"2024-01-02T00:00:00Z","timestamp":1704153600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT), Portugal","doi-asserted-by":"publisher","award":["UIDB\/00100\/2020","UIDP\/00100\/2020","LA\/P\/0056\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020","UIDP\/00100\/2020","LA\/P\/0056\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Following previous studies, the ternary mixture of methanol\/formamide\/acetonitrile (MeOH\/Formamide\/MeCN) was studied using the UV-Vis absorption spectra at 298.15 K with a set of five probes, 4-nitroaniline, 4-nitroanisole, 4-nitrophenol, N,N-dimethyl-4-nitroaniline and 2,6-diphenyl-4-(2,4,6-triphenyl-1-pyridinio)phenolate (Reichardt betaine dye), for a total of 22 mole ternary fractions. In addition, nine mole fractions of the underling binary mixtures, MeOH\/Formamide and Formamide\/MeCN were also tested. Spectroscopic results were used to model the preferential solvation order for each probe in the mixtures. The Kamlet\u2013Taft solvatochromic solvent parameters, \u03b1, \u03b2, and \u03c0*, were also computed through the use of the solvatochromic shifts of the five probe indicators. Moreover, discrepancies in the spectroscopic behavior of 4-nitrophenol in formamide-rich mixtures were observed and analyzed.<\/jats:p>","DOI":"10.3390\/molecules29010246","type":"journal-article","created":{"date-parts":[[2024,1,2]],"date-time":"2024-01-02T10:36:59Z","timestamp":1704191819000},"page":"246","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Study of the Ternary Mixture of Methanol\/Formamide\/Acetonitrile via Solvatochromic Probes"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4499-0379","authenticated-orcid":false,"given":"Nelson","family":"Nunes","sequence":"first","affiliation":[{"name":"Departamento de Engenharia Qu\u00edmica, Instituto Superior de Engenharia de Lisboa, Instituto Polit\u00e9cnico de Lisboa, Rua Conselheiro Em\u00eddio Navarro, 1959-007 Lisboa, Portugal"},{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Faculdade de Ci\u00eancias, Universidade de Lisboa, Ed. C8, Campo Grande, 1749-016 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2196-412X","authenticated-orcid":false,"given":"Ruben","family":"Elvas-Leit\u00e3o","sequence":"additional","affiliation":[{"name":"Departamento de Engenharia Qu\u00edmica, Instituto Superior de Engenharia de Lisboa, Instituto Polit\u00e9cnico de Lisboa, Rua Conselheiro Em\u00eddio Navarro, 1959-007 Lisboa, Portugal"},{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Faculdade de Ci\u00eancias, Universidade de Lisboa, Ed. C8, Campo Grande, 1749-016 Lisboa, Portugal"}]},{"given":"Filomena","family":"Martins","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Faculdade de Ci\u00eancias, Universidade de Lisboa, Ed. C8, Campo Grande, 1749-016 Lisboa, Portugal"},{"name":"Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Ed. C8, Campo Grande, 1749-016 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2319","DOI":"10.1021\/cr00032a005","article-title":"Solvatochromic Dyes as Solvent Polarity Indicators","volume":"94","author":"Reichardt","year":"1994","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1016\/j.molliq.2017.03.097","article-title":"Volumetric and Refractive Index Study of the Ternary Mixture Methanol\/Formamide\/Acetonitrile at 298.15 K","volume":"234","author":"Martins","year":"2017","journal-title":"J. Mol. Liq."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"470","DOI":"10.1016\/j.saa.2014.01.021","article-title":"UV\u2013Vis Spectroscopic Study of Preferential Solvation and Intermolecular Interactions in Methanol\/1-Propanol\/Acetonitrile by Means of Solvatochromic Probes","volume":"124","author":"Nunes","year":"2014","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"6027","DOI":"10.1021\/ja00460a031","article-title":"The Solvatochromic Comparison Method. 6. The .Pi.* Scale of Solvent Polarities","volume":"99","author":"Kamlet","year":"1977","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5807","DOI":"10.1021\/j100074a003","article-title":"The Empirical Treatment of Solvent-Solute Interactions: 15 Years of .Pi.*","volume":"98","author":"Laurence","year":"1994","journal-title":"J. Phys. Chem."},{"doi-asserted-by":"crossref","unstructured":"Nicolet, P., and Laurence, C. (1986). Polarity and Basicity of Solvents. Part 1. A Thermosolvatochromic Comparison Method. J. Chem. Soc. Perkin Trans. 2, 1071\u20131079.","key":"ref_6","DOI":"10.1039\/p29860001071"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1081","DOI":"10.1039\/p29860001081","article-title":"Polarity and Basicity of Solvents. Part 2. Solvatochromic Hydrogen-Bonding Shifts as Basicity Parameters","volume":"2","author":"Laurence","year":"1986","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2886","DOI":"10.1021\/ja00426a036","article-title":"The Solvatochromic Comparison Method. 2. The .Alpha.-Scale of Solvent Hydrogen-Bond Donor (HBD) Acidities","volume":"98","author":"Taft","year":"1976","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1616","DOI":"10.1039\/D0CP04989A","article-title":"The Physical Significance of the Kamlet\u2013Taft \u03c0* Parameter of Ionic Liquids","volume":"23","author":"Schmidt","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2177","DOI":"10.1039\/P29960002177","article-title":"Solute\u2013Solvent and Solvent\u2013Solvent Interactions in Binary Solvent Mixtures. Part 4. Preferential Solvation of Solvatochromic Indicators in Mixtures of 2-Methylpropan-2-Ol with Hexane, Benzene, Propan-2-Ol, Ethanol and Methanol","volume":"2","author":"Bosch","year":"1996","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2041","DOI":"10.1351\/pac197951102041","article-title":"Approaches to the Problems of Solvation in Pure Solvents and Preferential Solvation in Mixed Solvents","volume":"51","author":"Covington","year":"1979","journal-title":"Pure Appl. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1039\/f19878300495","article-title":"Local Polarity of Solvent Mixtures in the Field of Electronically Excited Molecules and Exciplexes","volume":"83","author":"Suppan","year":"1987","journal-title":"J. Chem. Soc. Faraday Trans. 1"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3311","DOI":"10.1021\/j100161a064","article-title":"Preferential Solvation of a Dipolar Solute in a Mixed Binary Solvent: A Study of UV-Visible Spectroscopy","volume":"95","author":"Chatterjee","year":"1991","journal-title":"J. Phys. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1002\/poc.632","article-title":"Thermo-Solvatochromism of Betaine Dyes in Aqueous Alcohols: Explicit Consideration of the Water\u2013Alcohol Complex","volume":"16","author":"Tada","year":"2003","journal-title":"J. Phys. Org. Chem."},{"key":"ref_15","first-page":"1607","article-title":"Solute\u2013Solvent and Solvent\u2013Solvent Interactions in Binary Solvent Mixtures. Part 1. A Comparison of Several Preferential Solvation Models for Describing ET(30) Polarity of Bipolar Hydrogen Bond Acceptor-Cosolvent Mixtures","volume":"2","author":"Ortega","year":"1995","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_16","first-page":"1341","article-title":"Solute\u2013Solvent and Solvent\u2013Solvent Interactions in Binary Solvent Mixtures. Part 6. A Quantitative Measurement of the Enhancement of the Water Structure in 2-Methylpropan-2-Ol\u2013Water and Propan-2-Ol\u2013Water Mixtures by Solvatochromic Indicators","volume":"2","author":"Buhvestov","year":"1997","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1002\/(SICI)1099-1395(199606)9:6<403::AID-POC799>3.0.CO;2-D","article-title":"Solute-Solvent and Solvent-Solvent Interactions in Binary Solvent Mixtures. 2. Effect of Temperature on the ET(30) Polarity Parameter of Dipolar Hydrogen Bond Acceptor-Hydrogen Bond Donor Mixtures","volume":"9","author":"Bosch","year":"1996","journal-title":"J. Phys. Org. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1497","DOI":"10.1039\/P29960001497","article-title":"Solute\u2013Solvent and Solvent\u2013Solvent Interactions in Binary Solvent Mixtures. Part 3. The ET(30) Polarity of Binary Mixtures of Hydroxylic Solvents","volume":"2","author":"Ortega","year":"1996","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_19","first-page":"243","article-title":"Solute\u2013Solvent and Solvent\u2013Solvent Interactions in Binary Solvent Mixtures. Part 5. Preferential Solvation of Solvatochromic Indicators in Mixtures of Propan-2-Ol with Hexane, Benzene, Ethanol and Methanol","volume":"2","author":"Bosch","year":"1997","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1002\/(SICI)1099-1395(199803)11:3<185::AID-POC993>3.0.CO;2-5","article-title":"Solute\u2013Solvent and Solvent\u2013Solvent Interactions in Binary Solvent Mixtures. Part 7. Comparison of the Enhancement of the Water Structure in Alcohol\u2013Water Mixtures Measured by Solvatochromic Indicators","volume":"11","author":"Buhvestov","year":"1998","journal-title":"J. Phys. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"140617","DOI":"10.1016\/j.cplett.2023.140617","article-title":"An, U.V. Visible Absorption Study of the Preferential Solvation of 4-Nitropyridine N-Oxide in Alcohol-Water Binary Mixture","volume":"825","author":"Mishra","year":"2023","journal-title":"Chem. Phys. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"115450","DOI":"10.1016\/j.molliq.2021.115450","article-title":"Preferential Solvation Index as a Tool in the Analysis of the Behavior of Solvatochromic Probes in Binary Solvent Mixtures","volume":"328","author":"Sandri","year":"2021","journal-title":"J. Mol. Liq."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3071","DOI":"10.1021\/jp804157b","article-title":"Modeling Preferential Solvation in Ternary Solvent Systems","volume":"113","author":"Nunes","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1002\/poc.520","article-title":"Structural Characterization of the Ternary Solvent Mixture Methanol-Acetonitrile-1-Propanol","volume":"15","author":"Martins","year":"2002","journal-title":"J. Phys. Org. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"12763","DOI":"10.1021\/acs.jpcb.1c06208","article-title":"The Role of Hydrogen Bonding in the Preferential Solvation of 5-Aminoquinoline in Binary Solvent Mixtures","volume":"125","author":"Das","year":"2021","journal-title":"J. Phys. Chem. B"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1007\/BF01074953","article-title":"The Effectiveness of Solvents as Hydrogen Bond Donors","volume":"20","author":"Marcus","year":"1991","journal-title":"J. Solut. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3613","DOI":"10.1021\/j100323a057","article-title":"Linear Solvation Energy Relationships: Standard Molar Gibbs Free Energies and Enthalpies of Transfer of Ions from Water into Nonaqueous Solvents","volume":"92","author":"Marcus","year":"1988","journal-title":"J. Phys. Chem."},{"key":"ref_28","first-page":"838","article-title":"IR Carbonyl Band Intensity Studies in N,N-Dimethyl Formamide and N,N-Dimethyl Acetamide on Complex Formation with Phenols","volume":"86","author":"Malathi","year":"2004","journal-title":"Curr. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.molliq.2003.08.020","article-title":"Dielectric Studies of H-Bonded Complexes of Formamide and Acetamide with Substituted Phenols","volume":"109","author":"Malathi","year":"2004","journal-title":"J. Mol. Liq."},{"key":"ref_30","first-page":"243","article-title":"Ab Initio Study on the H\u2014Bonding Complexes Formed from Phenol and a Series of Amides","volume":"20","author":"Shucai","year":"2000","journal-title":"Chin. J. Org. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/0022-2860(96)09230-7","article-title":"Recent Aspects of the Proton Transfer Reaction in H-Bonded Complexes","volume":"381","author":"Szafran","year":"1996","journal-title":"J. Mol. Struct."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/1\/246\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T13:38:29Z","timestamp":1760103509000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/1\/246"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,2]]},"references-count":31,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2024,1]]}},"alternative-id":["molecules29010246"],"URL":"https:\/\/doi.org\/10.3390\/molecules29010246","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2024,1,2]]}}}