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Article

Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines

by
Martin Havlík
1,
Tereza Navrátilová
1,
Michaela Drozdová
1,
Ameneh Tatar
1,
Priscila A. Lanza
2,
Diego Dusso
2,3,
Elizabeth Laura Moyano
3,
Carlos A. Chesta
4,
Domingo Mariano A. Vera
2,* and
Bohumil Dolenský
1,*
1
Department of Analytical Chemistry, University of Chemistry and Technology Prague, Technická 5, 166 28 Praha, Czech Republic
2
QUIAMM-INBIOTEC, Department of Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad Nacional de Mar del Plata, Mar del Plata B7602AYL, Argentina
3
INFIQC, Department of Organic Chemistry, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba 5000, Argentina
4
Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados (IITEMA), Universidad Nacional de Río Cuarto (UNRC), Consejo Nacional de Investigaciones Científicas y Tecnológicas (CONICET), Campus Universitario, Río Cuarto 5800, Argentina
*
Authors to whom correspondence should be addressed.
Molecules 2023, 28(4), 1549; https://doi.org/10.3390/molecules28041549
Submission received: 31 December 2022 / Revised: 31 January 2023 / Accepted: 3 February 2023 / Published: 6 February 2023
(This article belongs to the Special Issue Advances in Computational Spectroscopy)
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Abstract

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.
Keywords: methanal; naphthylamine; quinazoline; Tröger’s base; spiro-Tröger’s base; mechanisms; DFT methanal; naphthylamine; quinazoline; Tröger’s base; spiro-Tröger’s base; mechanisms; DFT

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MDPI and ACS Style

Havlík, M.; Navrátilová, T.; Drozdová, M.; Tatar, A.; Lanza, P.A.; Dusso, D.; Moyano, E.L.; Chesta, C.A.; Vera, D.M.A.; Dolenský, B. Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines. Molecules 2023, 28, 1549. https://doi.org/10.3390/molecules28041549

AMA Style

Havlík M, Navrátilová T, Drozdová M, Tatar A, Lanza PA, Dusso D, Moyano EL, Chesta CA, Vera DMA, Dolenský B. Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines. Molecules. 2023; 28(4):1549. https://doi.org/10.3390/molecules28041549

Chicago/Turabian Style

Havlík, Martin, Tereza Navrátilová, Michaela Drozdová, Ameneh Tatar, Priscila A. Lanza, Diego Dusso, Elizabeth Laura Moyano, Carlos A. Chesta, Domingo Mariano A. Vera, and Bohumil Dolenský. 2023. "Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines" Molecules 28, no. 4: 1549. https://doi.org/10.3390/molecules28041549

APA Style

Havlík, M., Navrátilová, T., Drozdová, M., Tatar, A., Lanza, P. A., Dusso, D., Moyano, E. L., Chesta, C. A., Vera, D. M. A., & Dolenský, B. (2023). Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines. Molecules, 28(4), 1549. https://doi.org/10.3390/molecules28041549

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