Effect of Terminal Hydroxy Groups on the Structural Properties of Acyl Thioureas.

Autor: Nossa González DL; CEQUINOR (UNLP-CONICET, CCT-La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Boulevard 120 e/ 60 y 64 N° 1465 La Plata, B1900, Buenos Aires, Argentina., Gómez Castaño JA; Grupo Química-Física Molecular y Modelamiento Computacional (QUIMOL), Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia, Sede Tunja, Avenida Central del Norte, Boyacá, 050030, Colombia., Echeverria GA; Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e Instituto de Física La Plata, IFLP (UNLP, CONICET, CCT-La Plata), C. C. 67, 1900, La Plata, Argentina., Piro OE; Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e Instituto de Física La Plata, IFLP (UNLP, CONICET, CCT-La Plata), C. C. 67, 1900, La Plata, Argentina., Saeed A; Department of Chemistry, Quaid-I-Azam University, Islamabad, 45320, Pakistan., Erben MF; CEQUINOR (UNLP-CONICET, CCT-La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Boulevard 120 e/ 60 y 64 N° 1465 La Plata, B1900, Buenos Aires, Argentina.
Jazyk: angličtina
Zdroj: Chemphyschem : a European journal of chemical physics and physical chemistry [Chemphyschem] 2024 Aug 08, pp. e202300680. Date of Electronic Publication: 2024 Aug 08.
DOI: 10.1002/cphc.202300680
Abstrakt: The 1-acyl thiourea family [R 1 C(O)NHC(S)NR 2 R 3 ] exhibits the flexibility to incorporate a wide variety of substituents into their structure. The structural attributes of these compounds are intricately tied to the type and extent of substitution. In the case of 3-mono-substituted thioureas (R 2 =H), the conformational behavior is predominantly shaped by the presence of an intramolecular N-H ⋅ ⋅ ⋅ O=C hydrogen bond. This study delves into the structural consequences stemming from the inclusion of substituents possessing hydrogen-donor capabilities within four novel 1-acyl-3-mono-substituted thiourea derivatives. A comprehensive suite of analytical techniques, encompassing FTIR, Raman spectroscopy, multinuclear ( 1 H and 13 C) NMR spectroscopy, single-crystal X-ray diffraction, and supported by computational methods, notably NBO (Natural Bond Orbital) population analysis, Hirshfeld analysis, and QTAIM (Quantum Theory of Atoms in Molecules), was harnessed to scrutinize and characterize these compounds. In the crystalline state, these compounds exhibit an intricate interplay of intermolecular interactions, prominently featuring an expansive network of hydrogen bonds between the hydroxy (-OH) groups and the carbonyl and thiocarbonyl bonds within the 1-acyl thiourea fragment. Notably, the topological analysis underscores significant distinctions in the properties of the acyl thiourea fragment and the intramolecular >C=O ⋅ ⋅ ⋅ H-N bond when transitioning from the isolated molecule to the crystalline environment.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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