{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,22]],"date-time":"2026-01-22T16:26:20Z","timestamp":1769099180162,"version":"3.49.0"},"reference-count":32,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,2,6]],"date-time":"2023-02-06T00:00:00Z","timestamp":1675641600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Education, Youth and Sports of the Czech Republic","award":["LTAUSA19065"],"award-info":[{"award-number":["LTAUSA19065"]}]},{"name":"Ministry of Education, Youth and Sports of the Czech Republic","award":["#11220200103033CO"],"award-info":[{"award-number":["#11220200103033CO"]}]},{"name":"National Council for Research and Technology","award":["LTAUSA19065"],"award-info":[{"award-number":["LTAUSA19065"]}]},{"name":"National Council for Research and Technology","award":["#11220200103033CO"],"award-info":[{"award-number":["#11220200103033CO"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The reactions of 2-naphthylamine and methyl 6-amino-2-naphthoate with formalin and paraformaldehyde were studied experimentally, spectrally, and by quantum chemical calculations. It was found that neither the corresponding aminals nor imines were formed under the described conditions but could be prepared and spectrally characterized at least in situ under modified conditions. Several of the previously undescribed intermediates and by-products were isolated or at least spectrally characterized. First principle density functional theory (DFT) calculations were performed to shed light on the key aspects of the thermochemistry of decomposition and further condensation of the corresponding aminals and imines. The calculations also revealed that the electrophilicity of methanal was significantly greater than that of ordinary oxo-compounds, except for perfluorinated ones. In summary, methanal was not behaving as the simplest aldehyde but as a very electron-deficient oxo-compound.<\/jats:p>","DOI":"10.3390\/molecules28041549","type":"journal-article","created":{"date-parts":[[2023,2,6]],"date-time":"2023-02-06T04:25:28Z","timestamp":1675657528000},"page":"1549","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Experimental, Spectroscopic, and Computational Insights into the Reactivity of \u201cMethanal\u201d with 2-Naphthylamines"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3250-6300","authenticated-orcid":false,"given":"Martin","family":"Havl\u00edk","sequence":"first","affiliation":[{"name":"Department of Analytical Chemistry, University of Chemistry and Technology Prague, Technick\u00e1 5, 166 28 Praha, Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8439-0370","authenticated-orcid":false,"given":"Tereza","family":"Navr\u00e1tilov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, University of Chemistry and Technology Prague, Technick\u00e1 5, 166 28 Praha, Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2197-6291","authenticated-orcid":false,"given":"Michaela","family":"Drozdov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, University of Chemistry and Technology Prague, Technick\u00e1 5, 166 28 Praha, Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ameneh","family":"Tatar","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, University of Chemistry and Technology Prague, Technick\u00e1 5, 166 28 Praha, Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Priscila A.","family":"Lanza","sequence":"additional","affiliation":[{"name":"QUIAMM-INBIOTEC, Department of Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad Nacional de Mar del Plata, Mar del Plata B7602AYL, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Diego","family":"Dusso","sequence":"additional","affiliation":[{"name":"QUIAMM-INBIOTEC, Department of Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad Nacional de Mar del Plata, Mar del Plata B7602AYL, Argentina"},{"name":"INFIQC, Department of Organic Chemistry, Facultad de Ciencias Qu\u00edmicas, Universidad Nacional de C\u00f3rdoba, C\u00f3rdoba 5000, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elizabeth Laura","family":"Moyano","sequence":"additional","affiliation":[{"name":"INFIQC, Department of Organic Chemistry, Facultad de Ciencias Qu\u00edmicas, Universidad Nacional de C\u00f3rdoba, C\u00f3rdoba 5000, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Carlos A.","family":"Chesta","sequence":"additional","affiliation":[{"name":"Instituto de Investigaciones en Tecnolog\u00edas Energ\u00e9ticas y Materiales Avanzados (IITEMA), Universidad Nacional de R\u00edo Cuarto (UNRC), Consejo Nacional de Investigaciones Cient\u00edficas y Tecnol\u00f3gicas (CONICET), Campus Universitario, R\u00edo Cuarto 5800, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Domingo Mariano A.","family":"Vera","sequence":"additional","affiliation":[{"name":"QUIAMM-INBIOTEC, Department of Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad Nacional de Mar del Plata, Mar del Plata B7602AYL, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5329-4490","authenticated-orcid":false,"given":"Bohumil","family":"Dolensk\u00fd","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, University of Chemistry and Technology Prague, Technick\u00e1 5, 166 28 Praha, Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1872","DOI":"10.1021\/ol1004774","article-title":"Spiro Tr\u00f6ger\u2019s Base Derivatives: Another Structural Phoenix?","volume":"12","author":"Tatar","year":"2010","journal-title":"Org. 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