The importance of attractive three-point interaction in enantioselective surface chemistry: stereospecific adsorption of serine on the intrinsically chiral Cu{531} surface

Journal of the American Chemical Society
Tugce EralpG Held

Abstract

Both enantiomers of serine adsorb on the intrinsically chiral Cu{531} surface in two different adsorption geometries, depending on the coverage. At saturation, substrate bonds are formed through the two oxygen atoms of the carboxylate group and the amino group (μ3 coordination), whereas at lower coverage, an additional bond is formed through the deprotonated β-OH group (μ4 coordination). The latter adsorption geometry involves substrate bonds through three side groups of the chiral center, respectively, which leads to significantly larger enantiomeric differences in adsorption geometries and energies compared to the μ3 coordination, which involves only two side groups. This relatively simple model system demonstrates, in direct comparison, that attractive interactions of three side groups with the substrate are much more effective in inducing strong enantiomeric differences in heterogeneous chiral catalyst systems than hydrogen bonds or repulsive interactions.

References

Apr 15, 1990·Physical Review. B, Condensed Matter·D Vanderbilt
May 20, 2004·Angewandte Chemie·Roman FaselThomas Greber
Jun 11, 2005·The Journal of Chemical Physics·Bhawna Bhatia, David S Sholl
Feb 21, 2006·Physical Review Letters·T GreberB Hammer
Jun 10, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Tugce EralpGeorg Held
Nov 26, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Tugce EralpTrolle R Linderoth

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Citations

May 18, 2017·Physical Chemistry Chemical Physics : PCCP·Michael J GladysLars Thomsen
May 27, 2017·Journal of the American Chemical Society·Yonghui WangWei Liu
Oct 19, 2017·Chemical Society Reviews·Francisco Zaera
Jun 30, 2015·Nanoscale·Huai-Song Wang, Ji-Ping Wei
Jun 19, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·José L C FajínM Natália D S Cordeiro
May 3, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Yongju Yun, Andrew J Gellman
Jul 25, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·Wilson QuevedoGeorg Held
Dec 29, 2017·Journal of the American Chemical Society·Aliaksandr V YakutovichCarlo A Pignedoli

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