Journal of the American Chemical Society 2009-04-22

H-atom position as pattern-determining factor in arenethiol films.

Ki-Young Kwon, Greg Pawin, Kin L Wong, Eric Peters, Daeho Kim, Sampyo Hong, Talat S Rahman, Michael Marsella, Ludwig Bartels

Index: J. Am. Chem. Soc. 131 , 5540, (2009)

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Abstract

The evolution of a low coverage of benzenethiol molecules on Cu(111) during annealing shows the prevalence of S...H hydrogen bonds involving hydrogen atoms in the ortho position. The row and pattern formation of (methylated) anthracenethiols indicates intermolecular interactions in which hydrogen atoms at the terminal position of the aromatic moiety dominate. In combination, this leads to the notion that pattern formation in classes of arenethiol molecules is each governed by optimization of the intermolecular interactions of the hydrogen atom at one particular position on the arene. This may provide a general guiding principle for the design of arenethiol films.