Abstract
The conformational, structural and electronic properties of eight acylthiourea derivatives with the general form N-acyl-N′, N′-alkylthiourea have been investigated computationally at the MP2 level of theory and the 6-311G(d) basis set. Transition states between the four stable conformations were identified and characterized. There is a good correlation between the electron density at the bond critical point of each of the three C–N bonds present in the molecules, the calculated bond length, and the rotational barrier around these bonds. The calculations suggest the C(S)-N′ bond to have considerable double bond character which, according to analysis in terms of the Natural Bond Orbitals paradigm, can be attributed to a more favorable delocalization of the N′ lone pair into the antibonding π*(C=S) orbital than the lone pair on the other nitrogen. The influence of the various substituents on the structural and energetic features of the acylthiourea backbone is also investigated.
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Woldu, M.G., Dillen, J. A quantum mechanical study of the stability and structural properties of substituted acylthiourea compounds. Theor Chem Account 121, 71–82 (2008). https://doi.org/10.1007/s00214-008-0451-6
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DOI: https://doi.org/10.1007/s00214-008-0451-6