skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Chiral Autocatalysis and Mirror Symmetry Breaking

Abstract

Not provided.

Authors:
;
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1537728
DOE Contract Number:  
SC0008703
Resource Type:
Journal Article
Journal Name:
Catalysis Letters
Additional Journal Information:
Journal Volume: 148; Journal Issue: 6; Journal ID: ISSN 1011-372X
Publisher:
Springer
Country of Publication:
United States
Language:
English
Subject:
Chemistry

Citation Formats

Gellman, Andrew J., and Ernst, Karl-Heinz. Chiral Autocatalysis and Mirror Symmetry Breaking. United States: N. p., 2018. Web. doi:10.1007/s10562-018-2380-x.
Gellman, Andrew J., & Ernst, Karl-Heinz. Chiral Autocatalysis and Mirror Symmetry Breaking. United States. doi:10.1007/s10562-018-2380-x.
Gellman, Andrew J., and Ernst, Karl-Heinz. Thu . "Chiral Autocatalysis and Mirror Symmetry Breaking". United States. doi:10.1007/s10562-018-2380-x.
@article{osti_1537728,
title = {Chiral Autocatalysis and Mirror Symmetry Breaking},
author = {Gellman, Andrew J. and Ernst, Karl-Heinz},
abstractNote = {Not provided.},
doi = {10.1007/s10562-018-2380-x},
journal = {Catalysis Letters},
issn = {1011-372X},
number = 6,
volume = 148,
place = {United States},
year = {2018},
month = {4}
}

Works referenced in this record:

Introduction:  Enantioselective Catalysis
journal, August 2003

  • Bolm, Carsten; Gladysz, J. A.
  • Chemical Reviews, Vol. 103, Issue 8
  • DOI: 10.1021/cr030693c

Homochiral imperative of molecular evolution
journal, January 1998


Chirality in adsorption on solid surfaces
journal, January 2017


Surface Chemistry for Enantioselective Catalysis
journal, October 2014

  • Gellman, Andrew J.; Tysoe, Wilfred T.; Zaera, Francisco
  • Catalysis Letters, Vol. 145, Issue 1
  • DOI: 10.1007/s10562-014-1400-8

Molecular chirality at surfaces
journal, September 2012


Beyond the surface atlas: A roadmap and gazetteer for surface symmetry and structure
journal, October 2007


Adsorption of Chiral Alcohols on “Chiral” Metal Surfaces
journal, January 1996

  • McFadden, Christopher F.; Cremer, Paul S.; Gellman, Andrew J.
  • Langmuir, Vol. 12, Issue 10
  • DOI: 10.1021/la950348l

Enantiospecific Adsorption of Amino Acids on Naturally Chiral Cu{3,1,17} R&S Surfaces
journal, May 2015


Equilibrium Adsorption of d - and l -Alanine Mixtures on Naturally Chiral Cu{3,1,17} R&S Surfaces
journal, June 2014

  • Yun, Yongju; Wei, Daniel; Sholl, David S.
  • The Journal of Physical Chemistry C, Vol. 118, Issue 27
  • DOI: 10.1021/jp503796u

Enantioselective Separation on Naturally Chiral Metal Surfaces: d,l -Aspartic Acid on Cu(3,1,17) R & S Surfaces
journal, February 2013

  • Yun, Yongju; Gellman, Andrew J.
  • Angewandte Chemie International Edition, Vol. 52, Issue 12
  • DOI: 10.1002/anie.201209025

Structure-sensitive enantiospecific adsorption on naturally chiral Cu( hkl ) R & S surfaces
journal, November 2016

  • Gellman, Andrew J.; Huang, Ye; Koritnik, Anjanette J.
  • Journal of Physics: Condensed Matter, Vol. 29, Issue 3
  • DOI: 10.1088/0953-8984/29/3/034001

Enantiospecific Desorption of Chiral Compounds from Chiral Cu(643) and Achiral Cu(111) Surfaces
journal, March 2002

  • Horvath, Joshua D.; Gellman, Andrew J.
  • Journal of the American Chemical Society, Vol. 124, Issue 10
  • DOI: 10.1021/ja012182i

Enantiospecific Desorption of R - and S -Propylene Oxide from a Chiral Cu(643) Surface
journal, August 2001

  • Horvath, Joshua D.; Gellman, Andrew J.
  • Journal of the American Chemical Society, Vol. 123, Issue 32
  • DOI: 10.1021/ja015890c

Kinetic aspects of non-linear effects in asymmetric synthesis, catalysis, and autocatalysis
journal, June 2010


Colloquium : Homochirality: Symmetry breaking in systems driven far from equilibrium
journal, April 2013


Catalyst testing at a lab scale in mild oxidation: Can you control the reaction temperature?
journal, May 1996


Catalytic autoignition of higher alkane partial oxidation on Rh-coated foams
journal, January 2006


Visualizing a Catalyst at Work during the Ignition of the Catalytic Partial Oxidation of Methane
journal, January 2009

  • Kimmerle, Bertram; Grunwaldt, Jan-Dierk; Baiker, Alfons
  • The Journal of Physical Chemistry C, Vol. 113, Issue 8
  • DOI: 10.1021/jp810319v

On spontaneous asymmetric synthesis
journal, January 1953


The origin and amplification of biomolecular chirality
journal, March 1991

  • Bonner, William A.
  • Origins of Life and Evolution of the Biosphere, Vol. 21, Issue 2
  • DOI: 10.1007/BF01809580

A concise summary of experimental facts about the Soai reaction
journal, January 2010

  • Gehring, Timo; Busch, Mark; Schlageter, Martin
  • Chirality, Vol. 22, Issue 1E
  • DOI: 10.1002/chir.20849

Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions
journal, November 2007

  • Mauksch, Michael; Tsogoeva, Svetlana B.; Wei, Shengwei
  • Chirality, Vol. 19, Issue 10
  • DOI: 10.1002/chir.20474

Evidence of Asymmetric Autocatalysis in Organocatalytic Reactions
journal, January 2007

  • Mauksch, Michael; Tsogoeva, Svetlana B.; Martynova, Irina M.
  • Angewandte Chemie International Edition, Vol. 46, Issue 3
  • DOI: 10.1002/anie.200603517

Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol
journal, January 1996

  • Shibata, Takanori; Morioka, Hiroshi; Hayase, Tadakatsu
  • Journal of the American Chemical Society, Vol. 118, Issue 2
  • DOI: 10.1021/ja953066g

Practically Perfect Asymmetric Autocatalysis with (2-Alkynyl-5-pyrimidyl)alkanols
journal, March 1999


d - and l -Quartz-Promoted Highly Enantioselective Synthesis of a Chiral Organic Compound
journal, December 1999

  • Soai, Kenso; Osanai, Shunji; Kadowaki, Kousuke
  • Journal of the American Chemical Society, Vol. 121, Issue 48
  • DOI: 10.1021/ja993128t

Asymmetric Autocatalysis: Triggered by Chiral Isotopomer Arising from Oxygen Isotope Substitution
journal, July 2011

  • Kawasaki, Tsuneomi; Okano, Yasushi; Suzuki, Etsuharu
  • Angewandte Chemie International Edition, Vol. 50, Issue 35
  • DOI: 10.1002/anie.201102263

Thermal desorption of gases
journal, July 1962


Surface explosion: HCOOH on Ni 〈110〉
journal, March 1974


Kinetic models of surface explosions
journal, August 1995


Surface “explosions” of acetate intermediates on Rh crystals and catalysts
journal, April 1994


From surface science to catalysis: Surface ?explosions? observed on Rh crystals and supported catalysts
journal, January 1993

  • Cassidy, T. J.; Allen, M. D.; Li, Y.
  • Catalysis Letters, Vol. 21, Issue 3-4
  • DOI: 10.1007/BF00769484

Chiral Recognition in Surface Explosion
journal, August 2004

  • Behzadi, Bahar; Romer, Sara; Fasel, Roman
  • Journal of the American Chemical Society, Vol. 126, Issue 30
  • DOI: 10.1021/ja048206d

Chemical Transformations, Molecular Transport, and Kinetic Barriers in Creating the Chiral Phase of (R, R)-Tartaric Acid on Cu(110)
journal, January 2002

  • Lorenzo, M. Ortega; Humblot, V.; Murray, P.
  • Journal of Catalysis, Vol. 205, Issue 1
  • DOI: 10.1006/jcat.2001.3422

Homochiral Conglomerates and Racemic Crystals in Two Dimensions: Tartaric Acid on Cu(110)
journal, July 2005

  • Romer, Sara; Behzadi, Bahar; Fasel, Roman
  • Chemistry - A European Journal, Vol. 11, Issue 14
  • DOI: 10.1002/chem.200400962

Unification of the matrix notation in molecular surface science
journal, June 2010


Superenantioselective Chiral Surface Explosions
journal, December 2013

  • Gellman, Andrew J.; Huang, Ye; Feng, Xu
  • Journal of the American Chemical Society, Vol. 135, Issue 51
  • DOI: 10.1021/ja408659v

Explosive enantiospecific decomposition of aspartic acid on Cu surfaces
journal, January 2016

  • Mhatre, B. S.; Dutta, S.; Reinicker, A.
  • Chemical Communications, Vol. 52, Issue 98
  • DOI: 10.1039/C6CC06887A

Selective adsorption of L- and D-amino acids on calcite: Implications for biochemical homochirality
journal, May 2001

  • Hazen, R. M.; Filley, T. R.; Goodfriend, G. A.
  • Proceedings of the National Academy of Sciences, Vol. 98, Issue 10
  • DOI: 10.1073/pnas.101085998

Remarkable Amplification of the Self-Disproportionation of Enantiomers on Achiral-Phase Chromatography Columns
journal, January 2006


Self-disproportionation of enantiomers via achiral chromatography: a warning and an extra dimension in optical purifications
journal, January 2012

  • Soloshonok, Vadim A.; Roussel, Christian; Kitagawa, Osamu
  • Chemical Society Reviews, Vol. 41, Issue 11
  • DOI: 10.1039/c2cs35006h

Competing Forces in Chiral Surface Chemistry: Enantiospecificity versus Enantiomer Aggregation
journal, November 2016


Adsorption-induced auto-amplification of enantiomeric excess on an achiral surface
journal, May 2015

  • Yun, Yongju; Gellman, Andrew J.
  • Nature Chemistry, Vol. 7, Issue 6
  • DOI: 10.1038/nchem.2250

The Macromolecular Route to Chiral Amplification
journal, November 1999


Macromolecular stereochemistry: the out-of-proportion influence of optically active comonomers on the conformational characteristics of polyisocyanates. The sergeants and soldiers experiment
journal, August 1989

  • Green, Mark M.; Reidy, Michael P.; Johnson, Robert D.
  • Journal of the American Chemical Society, Vol. 111, Issue 16, p. 6452-6454
  • DOI: 10.1021/ja00198a084

Majority Rules in the Copolymerization of Mirror Image Isomers
journal, April 1995

  • Green, Mark M.; Garetz, Bruce A.; Munoz, Beth
  • Journal of the American Chemical Society, Vol. 117, Issue 14
  • DOI: 10.1021/ja00119a039

Amplification of Chirality in Dynamic Supramolecular Aggregates
journal, December 2007

  • Palmans, Anja R. A.; Meijer, E. W.
  • Angewandte Chemie International Edition, Vol. 46, Issue 47
  • DOI: 10.1002/anie.200701285

“Majority-Rules” Operative in Chiral Columnar Stacks of C 3 -Symmetrical Molecules
journal, April 2005

  • van Gestel, Jeroen; Palmans, Anja R. A.; Titulaer, Bram
  • Journal of the American Chemical Society, Vol. 127, Issue 15
  • DOI: 10.1021/ja0501666

Amplification of Chirality at Solid Surfaces
journal, November 2009


Local and Global Chirality at Surfaces:  Succinic Acid versus Tartaric Acid on Cu(110)
journal, May 2004

  • Humblot, Vincent; Lorenzo, Maria Ortega; Baddeley, Christopher J.
  • Journal of the American Chemical Society, Vol. 126, Issue 20
  • DOI: 10.1021/ja0382056

Induction of Homochirality in Achiral Enantiomorphous Monolayers
journal, December 2004

  • Parschau, Manfred; Romer, Sara; Ernst, Karl-Heinz
  • Journal of the American Chemical Society, Vol. 126, Issue 47
  • DOI: 10.1021/ja044136z

Homochirality in monolayers of achiral meso tartaric acid
journal, May 2005


Stability of Chiral Domains Produced by Adsorption of Tartaric Acid Isomers on the Cu(110) Surface:  A Periodic Density Functional Theory Study
journal, July 2001

  • Barbosa, Luis Antonio M. M.; Sautet, Philippe
  • Journal of the American Chemical Society, Vol. 123, Issue 27
  • DOI: 10.1021/ja004336k

Determination of the Absolute Chirality of Adsorbed Molecules
journal, May 2004

  • Fasel, Roman; Wider, Joachim; Quitmann, Christoph
  • Angewandte Chemie International Edition, Vol. 43, Issue 21
  • DOI: 10.1002/anie.200353311

Two-Dimensional Self-Assembly of Chiral Malic Acid on Cu(110)
journal, September 2010

  • Roth, Christian; Passerone, Daniele; Merz, Leo
  • The Journal of Physical Chemistry C, Vol. 115, Issue 4
  • DOI: 10.1021/jp106575g

A metal surface with chiral memory
journal, January 2014

  • Karageorgaki, Chrysanthi; Ernst, Karl-Heinz
  • Chem. Commun., Vol. 50, Issue 15
  • DOI: 10.1039/C3CC48797K

Chiral reconstruction of Cu(110) after adsorption of fumaric acid
journal, November 2014


Dynamic control over supramolecular handedness by selecting chiral induction pathways at the solution–solid interface
journal, May 2016

  • Fang, Yuan; Ghijsens, Elke; Ivasenko, Oleksandr
  • Nature Chemistry, Vol. 8, Issue 7
  • DOI: 10.1038/nchem.2514

Globally homochiral assembly of two-dimensional molecular networks triggered by co-absorbers
journal, January 2013

  • Chen, Ting; Yang, Wen-Hong; Wang, Dong
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms2403

Emerging Solvent-Induced Homochirality by the Confinement of Achiral Molecules Against a Solid Surface
journal, June 2008

  • Katsonis, Nathalie; Xu, Hong; Haak, Robert M.
  • Angewandte Chemie International Edition, Vol. 47, Issue 27
  • DOI: 10.1002/anie.200800255

Amplification of chirality in two-dimensional enantiomorphous lattices
journal, January 2006

  • Fasel, Roman; Parschau, Manfred; Ernst, Karl-Heinz
  • Nature, Vol. 439, Issue 7075
  • DOI: 10.1038/nature04419

Coverage and Enantiomeric Excess Dependent Enantiomorphism in Two-Dimensional Molecular Crystals
journal, June 2008

  • Parschau, Manfred; Fasel, Roman; Ernst, Karl-Heinz
  • Crystal Growth & Design, Vol. 8, Issue 6
  • DOI: 10.1021/cg701100r

Chirality Transfer from Single Molecules into Self-Assembled Monolayers
journal, November 2003

  • Fasel, Roman; Parschau, Manfred; Ernst, Karl-Heinz
  • Angewandte Chemie International Edition, Vol. 42, Issue 42
  • DOI: 10.1002/anie.200352232

The formation of enantiospecific phases on a Cu{110} surface
journal, January 1999

  • Chen, Q.; W. Lee, C.; J. Frankel, D.
  • PhysChemComm, Vol. 2, Issue 9
  • DOI: 10.1039/a905986e

Drastic symmetry breaking in supramolecular organization of enantiomerically unbalanced monolayers at surfaces
journal, July 2009

  • Haq, Sam; Liu, Ning; Humblot, Vincent
  • Nature Chemistry, Vol. 1, Issue 5
  • DOI: 10.1038/nchem.295

Pasteur's quasiracemates in 2D: chiral conflict between structurally different enantiomers induces single-handed enantiomorphism
journal, January 2010

  • Roth, Christian; Passerone, Daniele; Ernst, Karl-Heinz
  • Chemical Communications, Vol. 46, Issue 45
  • DOI: 10.1039/c0cc03060k

Chiral Conflict among Different Helicenes Suppresses Formation of One Enantiomorph in 2D Crystallization
journal, May 2013

  • Seibel, Johannes; Allemann, Oliver; Siegel, Jay S.
  • Journal of the American Chemical Society, Vol. 135, Issue 20
  • DOI: 10.1021/ja402012j

LXIII.—Enantiomorphism
journal, January 1898

  • Kipping, Frederic Stanley; Pope, William Jackson
  • J. Chem. Soc., Trans., Vol. 73, Issue 0
  • DOI: 10.1039/CT8987300606

Chiral Symmetry Breaking in Sodium Chlorate Crystallizaton
journal, November 1990


Spontaneous Resolution by Stirred Crystallization
journal, March 1991

  • McBride, J. Michael; Carter, Randall L.
  • Angewandte Chemie International Edition in English, Vol. 30, Issue 3
  • DOI: 10.1002/anie.199102931

Complete Deracemization by Attrition-Enhanced Ostwald Ripening Elucidated
journal, August 2008

  • Noorduin, Wim L.; Meekes, Hugo; van Enckevort, Willem J. P.
  • Angewandte Chemie International Edition, Vol. 47, Issue 34
  • DOI: 10.1002/anie.200801846

Chiral Crystal Growth under Grinding
journal, November 2008

  • Saito, Yukio; Hyuga, Hiroyuki
  • Journal of the Physical Society of Japan, Vol. 77, Issue 11
  • DOI: 10.1143/JPSJ.77.113001

Did life grind to a start?
journal, March 2008

  • McBride, J. Michael; Tully, John C.
  • Nature, Vol. 452, Issue 7184
  • DOI: 10.1038/452161a

The Driving Mechanism Behind Attrition-Enhanced Deracemization
journal, September 2010

  • Noorduin, Wim L.; van Enckevort, Willem J. P.; Meekes, Hugo
  • Angewandte Chemie International Edition, Vol. 49, Issue 45
  • DOI: 10.1002/anie.201002036

Enantiomer-Specific Oriented Attachment: Formation of Macroscopic Homochiral Crystal Aggregates from a Racemic System
journal, August 2013

  • Viedma, Cristóbal; McBride, J. Michael; Kahr, Bart
  • Angewandte Chemie International Edition, Vol. 52, Issue 40
  • DOI: 10.1002/anie.201303915

Crystallization by particle attachment in synthetic, biogenic, and geologic environments
journal, July 2015

  • De Yoreo, J. J.; Gilbert, P. U. P. A.; Sommerdijk, N. A. J. M.
  • Science, Vol. 349, Issue 6247
  • DOI: 10.1126/science.aaa6760

Oriented attachment by enantioselective facet recognition in millimeter-sized gypsum crystals
journal, January 2016

  • Viedma, Cristóbal; Cuccia, Louis A.; McTaggart, Alicia
  • Chemical Communications, Vol. 52, Issue 78
  • DOI: 10.1039/C6CC06353E

Spontaneous Transition toward Chirality in the NaClO 3 Crystallization in Boiling Solutions
journal, November 2009

  • El-Hachemi, Zoubir; Crusats, Joaquim; Ribó, Josep M.
  • Crystal Growth & Design, Vol. 9, Issue 11
  • DOI: 10.1021/cg900638h

Metastability in Supersaturated Solution and Transition towards Chirality in the Crystallization of NaClO 3
journal, February 2011

  • El-Hachemi, Zoubir; Crusats, Joaquim; Ribó, Josep M.
  • Angewandte Chemie International Edition, Vol. 50, Issue 10
  • DOI: 10.1002/anie.201007209