Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution

1-Acyl thioureas [R1C(O)NHC(S)NR2R3] are shown to display conformational flexibility depending on the degree of substitution at the nitrogen atom. The conformational landscape and structural features for two closely related thioureas having R1 = 2-furoyl have been studied. The un-substituted 2-furoy...

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Autores principales:	Ramos Cairo, Raúl, Plutín Stevens, Ana María, Oliveira, Tamires D., Batista, Alzir A., Castellano, Eduardo E., Duque, Julio, Soria, Delia Beatriz, Fantoni, Adolfo Carlos, Corrêa, Rodrigo S., Erben, Mauricio Federico
Formato:	Articulo
Lenguaje:	Inglés
Publicado:	2017
Materias:	Química Thiourea derivatives Molecular conformation Single crystal structure determination Vibrational spectroscopy Hirshfeld surface analysis Topological study
Acceso en línea:	http://sedici.unlp.edu.ar/handle/10915/104881
Aporte de:	SEDICI (UNLP) de Universidad Nacional de La Plata

id	I19-R120-10915-104881
record_format	dspace
institution	Universidad Nacional de La Plata
institution_str	I-19
repository_str	R-120
collection	SEDICI (UNLP)
language	Inglés
topic	Química Thiourea derivatives Molecular conformation Single crystal structure determination Vibrational spectroscopy Hirshfeld surface analysis Topological study
spellingShingle	Química Thiourea derivatives Molecular conformation Single crystal structure determination Vibrational spectroscopy Hirshfeld surface analysis Topological study Ramos Cairo, Raúl Plutín Stevens, Ana María Oliveira, Tamires D. Batista, Alzir A. Castellano, Eduardo E. Duque, Julio Soria, Delia Beatriz Fantoni, Adolfo Carlos Corrêa, Rodrigo S. Erben, Mauricio Federico Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
topic_facet	Química Thiourea derivatives Molecular conformation Single crystal structure determination Vibrational spectroscopy Hirshfeld surface analysis Topological study
description	1-Acyl thioureas [R1C(O)NHC(S)NR2R3] are shown to display conformational flexibility depending on the degree of substitution at the nitrogen atom. The conformational landscape and structural features for two closely related thioureas having R1 = 2-furoyl have been studied. The un-substituted 2-furoyl thiourea (I) and its dimethyl analogue, i.e. 1-(2-furoyl)-3,3-dimethyl thiourea (II), have been synthesized and fully characterized by spectroscopic (FT-IR, 1H and 13C NMR) and elemental analysis. According to single crystal X-ray diffraction analysis, compounds I and II crystallize in the monoclinic space group P21/c. In the compound I, the trans–cis geometry of the almost planar thiourea unit is stabilized by intramolecular Nsingle bondH ⋯ Odouble bondC hydrogen bond between the H atom of the cis thioamide and the carbonyl O atom. In compound II, however, the acyl thiourea group is non-planar, in good agreement with the potential energy curve computed at the B3LYP/6-31 + G(d,p) level of approximation. Centrosymmetric dimers generated by intermolecular N — H ⋯ O = C hydrogen bond forming R22(8) motif are present in the crystals. Intermolecular interactions have been rationalized in terms of topological partitions of the electron distributions and Hirshfeld surface analysis, which showed the occurrence of S ⋯ H, O ⋯ H and H ⋯ H contacts that display an important role to crystal packing stabilization of both thiourea derivatives.
format	Articulo Articulo
author	Ramos Cairo, Raúl Plutín Stevens, Ana María Oliveira, Tamires D. Batista, Alzir A. Castellano, Eduardo E. Duque, Julio Soria, Delia Beatriz Fantoni, Adolfo Carlos Corrêa, Rodrigo S. Erben, Mauricio Federico
author_facet	Ramos Cairo, Raúl Plutín Stevens, Ana María Oliveira, Tamires D. Batista, Alzir A. Castellano, Eduardo E. Duque, Julio Soria, Delia Beatriz Fantoni, Adolfo Carlos Corrêa, Rodrigo S. Erben, Mauricio Federico
author_sort	Ramos Cairo, Raúl
title	Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_short	Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_full	Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_fullStr	Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_full_unstemmed	Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_sort	understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
publishDate	2017
url	http://sedici.unlp.edu.ar/handle/10915/104881
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bdutipo_str	Repositorios
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Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution

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