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Issue 11, 2001
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Synthesis, characterization and thermochemical properties of N-acyl-N′,N′-diethylthioureas

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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 dioxanewater 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


Submitted
30 May 2001
Accepted
06 Sep 2001
First published
05 Oct 2001

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

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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