Issue 11, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Synthesis, characterization and thermochemical properties of N-acyl-N′,N′-diethylthioureas

Manuel A. V. Ribeiro da Silva,*a   Maria D. M. C. Ribeiro da Silva,a   Luís C. M. da Silva,a   Frank Dietze,b   Eberhard Hoyer,b   Lothar Beyer,b   Bernd Schröder,b   Ana M. Damasc  and  Joel F. Liebman*d  

* Corresponding authors

a Centro de Investigação em Química, Departamento de Química, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal

b Institut für Anorganische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, Leipzig 04103, Bundesrepublik Deutschland

c Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Largo do Prof. Abel Salazar, 2, Rua do Campo Alegre, 823, P-4150-180 Porto, Portugal, Portugal

d Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, USA

Abstract

Three N-acyl-N′,N′-diethylthioureas, RCONHCSNEt2, R = iPr, iBu, tBu, have been prepared and characterised. The standard (po = 0.1 MPa) molar enthalpies of combustion in oxygen of the three crystalline compounds, at T = 298.15 K, have been measured by rotating bomb-combustion calorimetry, and the standard molar enthalpies of sublimation of the compounds by microcalorimetry. These values were used to derive the standard molar enthalpies of formation of the compounds in their crystalline and gaseous phases, respectively. The derived standard molar enthalpies of formation in the gaseous state are discussed comparatively. Acid constants and some complex stabilities have been measured pH-potentiometrically in dioxane–water mixture. The crystal structure of N,N-diethyl-N′-isovaleroylthiourea is presented and shows a delocalization of the π electrons of the C[double bond, length as m-dash]S group over the carbon–amine nitrogen bond, CS–NEt2, stabilising the molecule, in accordance with the thermochemical results.

Graphical abstract: Synthesis, characterization and thermochemical properties of N-acyl-N′,N′-diethylthioureas

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Article information

DOI
https://doi.org/10.1039/B104709B
Article type
Paper
Submitted
30 May 2001
Accepted
06 Sep 2001
First published
05 Oct 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 2174-2178

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Synthesis, characterization and thermochemical properties of N-acyl-N′,N′-diethylthioureas

M. A. V. Ribeiro da Silva, M. D. M. C. Ribeiro da Silva, L. C. M. da Silva, F. Dietze, E. Hoyer, L. Beyer, B. Schröder, A. M. Damas and J. F. Liebman, J. Chem. Soc., Perkin Trans. 2, 2001, 2174 DOI: 10.1039/B104709B

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