The Journal of Organic Chemistry
Wiley - VCH Verlag GmbH & Co. KGaA
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.
nziko, v. d. P. N., Scheiner, S. I. (2015). Interactions between Thiourea and Imines. Prelude to Catalysis. J. Org. Chem., 54, 10334–10341.
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 https://doi.org/10.1021/acs.joc.5b01985. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.