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Journal/Book Title

The Journal of Organic Chemistry

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Wiley - VCH Verlag GmbH & Co. KGaA





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The interaction between thiourea and a series of imines was examined via high-level ab initio calculations. For each imine, there is a set of stable complexes that represent minima on the potential energy surface. One type is characterized by a pair of symmetric NH···N hydrogen bonds (HBs), with both NH groups of thiourea approaching the imine N from above and below its molecular plane. Another geometry category combines a linear NH···N with a CH···S HB. A third, which is less stable, has the S approaching the imine’s CH2 group, and a stacking arrangement is present in the fourth. Interaction energies vary from ∼2 kcal/mol to a maximum of 13.5 kcal/mol. The formation of the complex tends to elongate the C−N bond within the imine by as much as 0.004 Å, but there are certain dimers that cause a small contraction of this bond.


This is the peer reviewed version of the following article: nziko, v. d. P. N., Scheiner, S. I. (2015). Interactions between Thiourea and Imines. Prelude to Catalysis. J. Org. Chem., 54, 10334–10341., which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.

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