Structural characterization of a series of aryl selenoacetates

Se-mesityl ethaneselenoate, Se-4-(dimethylamino)phenyl ethaneselenoate, Se-anthracen-9-yl ethaneselenoate, and Se-(4'-cyanobiphenyl-4-yl) ethaneselenoate, potential building blocks for selenium-anchored self-assembled monolayers on metal surfaces, were examined and characterized using single crystal X-ray diffraction, Fourier-transform infrared (FT-IR) spectroscopy, and density functional theory (DFT) calculations. The molecules all adopt similar conformations with the selenoacetate unit being tilted between 61 degrees and 78 degrees with respect to the adjacent arene ring and binding angles of 97-100 degrees at the selenium atom. An interesting feature is that the oxygen atom of the acetyl group always points toward the arene system, a feature correctly reproduced by the DFT calculations. The calculations could also predict the IR spectra of the compounds, making a detailed interpretation possible. (C) 2013 Elsevier B.V. All rights reserved.