Enantiospecific Chemisorption of Small Molecules on Intrinsically Chiral Cu Surfaces

Bhatia, Bhawna; Sholl, David S.

doi:10.1002/anie.200501655

Cited by 53 publications

(66 citation statements)

References 28 publications

(42 reference statements)

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“…This is in agreement with the DFT study of Ref. [38] where the most stable adsorption sites involve a bond between the kink Cu atom and the oxygen atom of propylene oxide.…”

Section: Chiral Surfacessupporting

confidence: 90%

“…The differences in desorption temperatures are equivalent to differences in the adsorption energies of 1.0 kJ/mol ((R)-3-methyl cyclohexanone on (S) substrate is more stable) and 0.3 kJ/mol ((R)-propylene oxide on (R) substrate is more stable). DFT calculations by Bhatia and Sholl [38] for propylene oxide on Cu{874} lead to a similar adsorption energy difference between the two enantiomers of 2.0 kJ/ mol (0.02 eV per molecule; (R)-propylene oxide on (S) substrate is more stable).…”

Section: Chiral Surfacesmentioning

confidence: 84%

“…Theoretical studies commonly find that the adsorption energy minima for a number of different adsorption geometries are all within the confidence limit of about 0.1 eV per molecule (e.g. [16,28,38]). Therefore, an independent experimental determination of the adsorption geometry is crucial at this stage.…”

Section: Adsorption Geometriesmentioning

confidence: 99%

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The Chemistry of Intrinsically Chiral Surfaces

Held

Gladys

2008

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Intrinsically chiral metal and mineral surfaces show enantioselective behaviour without modifiers. Examples are artificial high-Miller-index surfaces of metal single crystals with cubic bulk lattice symmetry, which have no mirror planes and are therefore chiral, or surfaces of naturally occurring crystallites of some common minerals, such as a-quartz or calcite. Recent findings with regards to the surface geometry, reactivity and thermal stability of intrinsically chiral surfaces are discussed. A number of enantioselective effects have been reported in connection with the adsorption of small chiral molecules (e.g. alanine, cysteine) on intrinsically chiral surfaces under well-defined conditions. From a combination of experimental surface science techniques and theoretical ab initio model calculations it emerges that these effects are due to a combination of attractive and repulsive adsorbate-substrate and inter-adsorbate interactions.

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“…This is in agreement with the DFT study of Ref. [38] where the most stable adsorption sites involve a bond between the kink Cu atom and the oxygen atom of propylene oxide.…”

Section: Chiral Surfacessupporting

confidence: 90%

Section: Chiral Surfacesmentioning

confidence: 84%

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The Chemistry of Intrinsically Chiral Surfaces

Held

Gladys

2008

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“…More detailed crystallographic information about the number and nature of enantiospecific interactions between chiral adsorbates and a metal surface emerged over the last few years, both from theory and experiment [19][20][21][22][23][24][25][26][27]. The first combination of experimental and theoretical work in this context was a combined DFT and photoelectron diffraction study of enantioselective effects in the adsorption geometry of cysteine on Au{17 11 9} by Greber et al [22].…”

Section: Introductionmentioning

confidence: 99%

The Study of Chiral Adsorption Systems Using Synchrotron-Based Structural and Spectroscopic Techniques: Stereospecific Adsorption of Serine on Au-Modified Chiral Cu{531} Surfaces

et al. 2011

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We apply modern synchrotron-based structural techniques to the study of serine adsorbed on the pure and Aumodified intrinsically chiral Cu{531} surface. XPS and NEXAFS data in combination with DFT show that on the pure surface both enantiomers adsorb in l 4 geometries (with de-protonated b-OH groups) at low coverage and in l 3 geometries at saturation coverage. Significantly larger enantiomeric differences are seen for the l 4 geometries, which involve substrate bonds of three side groups of the chiral center, i.e. a three-point interaction. The l 3 adsorption geometry, where only the carboxylate and amino groups form substrate bonds, leads to smaller but still significant enantiomeric differences, both in geometry and the decomposition behavior. When Cu{531} is modified by the deposition of 1 and 2 ML Au the orientations of serine at saturation coverage are significantly different from those on the clean surface. In all cases, however, a l 3 bond coordination is found at saturation involving different numbers of Au atoms, which leads to relatively small enantiomeric differences.

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“…It is well established that certain surface terminations are chiral [55,56] and that such surfaces can behave enantioselectively [57,58]. However, on the surface of a typical metal particle, there will be a racemic mixture of surface terminations, making the overall catalyst achiral.…”

Section: Achiral Molecules On Achiral Surfaces -The Racemic Reactionmentioning

confidence: 99%

Enantioselective Heterogeneous Catalysis

Baddeley

2013

Heterogeneous Catalysts for Clean Technology

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Enantiospecific Chemisorption of Small Molecules on Intrinsically Chiral Cu Surfaces

Cited by 53 publications

References 28 publications

The Chemistry of Intrinsically Chiral Surfaces

The Chemistry of Intrinsically Chiral Surfaces

The Study of Chiral Adsorption Systems Using Synchrotron-Based Structural and Spectroscopic Techniques: Stereospecific Adsorption of Serine on Au-Modified Chiral Cu{531} Surfaces

Enantioselective Heterogeneous Catalysis

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