The DOI matches its Crossref record; 35 of the 35 references it cites were found in a registry or an index.
Violation of Distribution Symmetry in Statistical Evaluation of Absolute Enantioselective Synthesis
Abstract
Enantiomeric excesses obtained in absolute enantioselective synthesis by chiral autocatalysis (Soai-reaction) were statistically analyzed. Two sets of parallel experiments, which were performed under chemically different conditions, are available. One group contains 37, while the other contains 84 preparative results. The former group shows some interesting tendencies but does not give conclusive statistical results. The sample of 84 parallel experiments, providing 39 R- and 45 S-excesses have shown that these data represent two distinct, non-symmetric sets with different non-Gaussian distributions. Clear S preference was found.
Overview
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The outcome of the Soai reaction in absence of detectable chiral species is stochastic.
“In addition, the apparent outcome of the Soai reaction performed in the absence of detectable chiral species is stochastic as expected for a truly SMSB process”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [329]
Citations
Cites
Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule
Soai, K., Shibata, T., Morioka, H., & Choji, K. (1995) · Nature · doi:10.1038/378767a0 · Cited by 1,085
Chiral Symmetry Breaking in Sodium Chlorate Crystallization
Kondepudi, D. K., Kaufman, R. J., & Singh, N. (1990) · Science · doi:10.1126/science.250.4983.975 · Cited by 965
Asymmetric photochemical reactions in solution
Inoue, Y. (1992) · Chemical Reviews · doi:10.1021/cr00013a001 · Cited by 657
How Important is Parity Violation for Molecular and Biomolecular Chirality?
Quack, M. (2002) · Angewandte Chemie International Edition · doi:10.1002/anie.200290005 · Cited by 441
Weak neutral currents and the origin of biomolecular chirality
Kondepudi, D. K., & Nelson, G. W. (1985) · Nature · doi:10.1038/314438a0 · Cited by 378
Kawasaki, T., Sato, M., Ishiguro, S., Saito, T., Morishita, Y., Sato, I., Nishino, H., Inoue, Y., & Soai, K. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0422108 · Cited by 305
Absolute Asymmetric Synthesis: A Commentary
Mislow, K. (2003) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc20030849 · Cited by 286
A hypothesis for the asymmetric appearance of biomolecules on earth
Yamagata, Y. (1966) · Journal of Theoretical Biology · doi:10.1016/0022-5193(66)90110-x · Cited by 271
Soai, K., Sato, I., Shibata, T., Komiya, S., Hayashi, M., Matsueda, Y., Imamura, H., Hayase, T., Morioka, H., Tabira, H., et al. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(02)00791-7 · Cited by 266
Optische Aktivit�t und die Parit�tsverletzung im ?-Zerfall
Vester, F., Ulbricht, T. L. V., & Krauch, H. (1959) · Die Naturwissenschaften · doi:10.1007/bf00599091 · Cited by 163
Carlucci, L., Ciani, G., Proserpio, D. M., & Porta, F. M. (2003) · Angewandte Chemie International Edition · doi:10.1002/anie.200390106 · Cited by 156
Gridnev, I. D., Serafimov, J. M., & Brown, J. M. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200353572 · Cited by 140
Sato, I., Omiya, D., Igarashi, H., Kato, K., Ogi, Y., Tsukiyama, K., & Soai, K. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(03)00164-2 · Cited by 138
Origin of the homochirality of biomolecules
Keszthelyi, L. (1995) · Quarterly Reviews of Biophysics · doi:10.1017/s0033583500003309 · Cited by 130
Enantioselective Synthesis without Discrete Optically Active Additives
Singleton, D. A., & Vo, L. K. (2002) · Journal of the American Chemical Society · doi:10.1021/ja027129o · Cited by 118
Progress in Biological Chirality
(2004) · Elsevier eBooks · doi:10.1016/b978-0-08-044396-6.x5000-x · Cited by 115
Demonstration of the parity-violating energy difference between enantiomers
Szabó-Nagy, A., & Keszthelyi, L. (1999) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.96.8.4252 · Cited by 110
Kawasaki, T., Suzuki, K., Shimizu, M., Ishikawa, K., & Soai, K. (2006) · Chirality · doi:10.1002/chir.20273 · Cited by 109
(1999) · Elsevier eBooks · doi:10.1016/b978-0-08-043404-9.x5000-1 · Cited by 97
New Aspects of Soai's Asymmetric Autocatalysis
Podlech, J., & Gehring, T. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200501742 · Cited by 87
Photochemistry with Circularly Polarized Light
Buchardt, O. (1974) · Angewandte Chemie International Edition in English · doi:10.1002/anie.197401791 · Cited by 85
A tentative kinetic model for chiral amplification in autocatalytic alkylzinc additions
Buhse, T. (2003) · Tetrahedron Asymmetry · doi:10.1016/s0957-4166(03)00128-9 · Cited by 75
Mechanistic study of the Soai autocatalytic reaction informed by kinetic analysis
Blackmond, D. G. (2006) · Tetrahedron Asymmetry · doi:10.1016/j.tetasy.2006.01.012 · Cited by 66
Homogeneous Chiral Autocatalysis: A Simple, Purely Stochastic Kinetic Model
Lente, G. (2004) · The Journal of Physical Chemistry A · doi:10.1021/jp046413u · Cited by 62
Empirical Description of Chiral Autocatalysis
Micskei, K., Póta, G., Caglioti, L., & Pályi, G. (2006) · The Journal of Physical Chemistry A · doi:10.1021/jp0614502 · Cited by 53
Self-citationPhotochemical Concepts on the Origin of Biomolecular Asymmetry
Meierhenrich, U. J., & Thiemann, W. (2003) · Origins of Life and Evolution of Biospheres · doi:10.1023/b:orig.0000009832.71546.1d · Cited by 47
Ueber Thioderivate des β‐Naphtols
Henriques, R. (1894) · Berichte der deutschen chemischen Gesellschaft · doi:10.1002/cber.18940270365 · Cited by 42
Parity Violation Energy Of Biomolecules – I: Polypeptides
Faglioni, F., Passalacqua, A., & Lazzeretti, P. (2005) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-005-3511-0 · Cited by 30
Generalization possibilities of autocatalytic absolute enantioselective synthesis
Micskei, K., Maioli, M., Zucchi, C., Caglioti, L., & Pályi, G. (2006) · Tetrahedron Asymmetry · doi:10.1016/j.tetasy.2006.11.016 · Cited by 26
Self-citationParity violation energy of biomolecules – II: DNA
Faglioni, F., D’Agostino, P. S., Cadioli, B., & Lazzeretti, P. (2005) · Chemical Physics Letters · doi:10.1016/j.cplett.2005.04.009 · Cited by 20
Synthese der α‐Amino‐γ‐oxy‐buttersäure
Fischer, E., & Blumenthal, H. (1907) · Berichte der deutschen chemischen Gesellschaft · doi:10.1002/cber.19070400112 · Cited by 16
Parity violation energy of 5-pyrimidyl alkanol, a chiral autocatalytic molecule
Faglioni, F., Lazzeretti, P., & Pályi, G. (2006) · Chemical Physics Letters · doi:10.1016/j.cplett.2006.12.069 · Cited by 12
Self-citationScience, Industry, and the Abuse of Rights of Way
Egler, F. E. (1958) · Science · doi:10.1126/science.127.3298.573 · Cited by 11
Siegel, J. S. (1998) · Chirality · doi:10.1002/chir.2 · Cited by 7
Absolute Asymmetric Synthesis: The Origin, Control, and Amplification of Chirality
Feringa, B. L., & van Delden, R. A. (1999) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(19991203)38:23
Flagged first, then by citations
Research works printed but not linked: 19
- Pályi G., 2005, Magy. Kem. Lapja, 60, 17
- Boutaric A., 1941, Rev. Sci., 79, 385
- Pályi G., 2001, Atti Accad. Naz. Sci. Lett. Arti (Modena), 317, 477
- Kuhn W., 1930, Z. Physik. Chem. B, 7, 310
- Keszthelyi, 2002, Fundamentals of Life, 387
- Pearson K., 1898, Nature, 58, 496
- Mills W. H., 1932, Chem. Ind. (London), 750, 759
- Caglioti L., 2006, Viva Origino, 34, 80
- Lee T. D., 1956, Phys. Rev., 104, 258
- Compton R. N., 2002, Adv. At., Mol., Opt. Phys., 48, 261
- Pályi G., 2003, Magy. Kem. Lapja, 58, 233
- Maioli M., 2007, Accepted for publication
- Rényi A., 1970, Probability Theory
- Reimann J., 1989, Mathemathical Statistics with Application in Flood Hydrology
- Piccolo D., 1998, Italy, 674
- Baldi, P. Calcolo delle probabilità e statistica ; McGraw-Hill Italia: Milano, Italy, 1998; p 138.
- Bartoszynski, R.; Niewiadomska-Bugaj, M. Probability and Statistical Inference ; Wiley: New York, 1996; pp 729, 810.
- Caglioti L., 2005, Chem. Today, 23, 43
- Rivera-Islas J., 2005, Proc. Natl. Acad. Sci. U.S.A., 102, 13748
Cited by
Sorted by citations
Buhse, T., Cruz, J.-M., Noble-Terán, M. E., Hochberg, D., Ribó, J. M., Crusats, J., & Micheau, J.-C. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00819 · Cited by 189
Possible chemical and physical scenarios towards biological homochirality
Sallembien, Q., Bouteiller, L., Crassous, J., & Raynal, M. (2022) · Chemical Society Reviews · doi:10.1039/d1cs01179k · Cited by 186
Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis
Barabás, B., Zucchi, C., Maioli, M., Micskei, K., & Pályi, G. (2015) · Journal of Molecular Modeling · doi:10.1007/s00894-015-2576-6 · Cited by 168
Self-citationSchiaffino, L., & Ercolani, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802450 · Cited by 100
Ercolani, G., & Schiaffino, L. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo102525t · Cited by 86
Gridnev, I. D., & Vorobiev, A. K. (2012) · ACS Catalysis · doi:10.1021/cs300497h · Cited by 84
A concise summary of experimental facts about the Soai reaction
Gehring, T., Busch, M., Schlageter, M., & Weingand, D. (2010) · Chirality · doi:10.1002/chir.20849 · Cited by 82
Oscillatory Symmetry Breaking in the Soai Reaction
Micskei, K., Rábai, G., Gál, E., Caglioti, L., & Pályi, G. (2008) · The Journal of Physical Chemistry B · doi:10.1021/jp803334b · Cited by 80
Self-citationMatsumoto, A., Abe, T., Hara, A., Tobita, T., Sasagawa, T., Kawasaki, T., & Soai, K. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201508036 · Cited by 75
Re-Examination of Reversibility in Reaction Models for the Spontaneous Emergence of Homochirality
Blackmond, D. G., & Matar, O. K. (2008) · The Journal of Physical Chemistry B · doi:10.1021/jp7118586 · Cited by 70
Stochastic aspects of asymmetric autocatalysis and absolute asymmetric synthesis
Barabás, B., Tóth, J., & Pályi, G. (2010) · Journal of Mathematical Chemistry · doi:10.1007/s10910-010-9680-8 · Cited by 67
Self-citationDóka, É., & Lente, G. (2011) · Journal of the American Chemical Society · doi:10.1021/ja207408y · Cited by 60
The Role of Stochastic Models in Interpreting the Origins of Biological Chirality
Lente, G. (2010) · Symmetry · doi:10.3390/sym2020767 · Cited by 59
Amplification of Chirality and Enantioselectivity in the Asymmetric Autocatalytic Soai Reaction
Schiaffino, L., & Ercolani, G. (2009) · ChemPhysChem · doi:10.1002/cphc.200900369 · Cited by 51
Mechanism of the Asymmetric Autocatalytic Soai Reaction Studied by Density Functional Theory
Schiaffino, L., & Ercolani, G. (2010) · Chemistry - A European Journal · doi:10.1002/chem.200902543 · Cited by 50
Soai, K., Kawasaki, T., & Matsumoto, A. (2018) · Tetrahedron · doi:10.1016/j.tet.2018.02.040 · Cited by 48
Role of Asymmetric Autocatalysis in the Elucidation of Origins of Homochirality of Organic Compounds
Soai, K., Kawasaki, T., & Matsumoto, A. (2019) · Symmetry · doi:10.3390/sym11050694 · Cited by 44
Busch, M., Schlageter, M., Weingand, D., & Gehring, T. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200900634 · Cited by 41
Data-Based Stochastic Approach to Absolute Asymmetric Synthesis by Autocatalysis
Barabás, B., Caglioti, L., Micskei, K., & Pályi, G. (2009) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.82.1372 · Cited by 36
Self-citationThe effect of parity violation on kinetic models of enantioselective autocatalysis
Lente, G. (2007) · Physical Chemistry Chemical Physics · doi:10.1039/b711546f · Cited by 36
Schiaffino, L., & Ercolani, G. (2008) · Angewandte Chemie · doi:10.1002/ange.200802450 · Cited by 28
Montigny, F. D., Bast, R., Gomes, A. S. P., Pilet, G., Vanthuyne, N., Roussel, C., Guy, L., Schwerdtfeger, P., Saue, T., & Crassous, J. (2010) · Physical Chemistry Chemical Physics · doi:10.1039/b925050f · Cited by 26
Elucidation of the Structures of Asymmetric Autocatalyst Based on X-ray Crystallography
Matsumoto, A., Fujiwara, S., Abe, T., Hara, A., Tobita, T., Sasagawa, T., Kawasaki, T., & Soai, K. (2016) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.20160160 · Cited by 24
Natural Abundance Isotopic Chirality in the Reagents of the Soai Reaction
Barabás, B., Kurdi, R., & Pályi, G. (2016) · Symmetry · doi:10.3390/sym8010002 · Cited by 18
Self-citationMatsumoto, A., Abe, T., Hara, A., Tobita, T., Sasagawa, T., Kawasaki, T., & Soai, K. (2015) · Angewandte Chemie · doi:10.1002/ange.201508036 · Cited by 18
Ercolani, G. (2014) · Tetrahedron Asymmetry · doi:10.1016/j.tetasy.2014.02.005 · Cited by 16
Limits of the Classical Concept of Concentration
Maioli, M., Varadi, G., Kurdi, R., Caglioti, L., & Pályi, G. (2016) · The Journal of Physical Chemistry B · doi:10.1021/acs.jpcb.6b02904 · Cited by 13
Self-citationLente, G. (2011) · Tetrahedron Asymmetry · doi:10.1016/j.tetasy.2011.09.016 · Cited by 11
Matsumoto, A., Tanaka, A., Kaimori, Y., Hara, N., Mikata, Y., & Soai, K. (2021) · Chemical Communications · doi:10.1039/d1cc04206h · Cited by 10
Single chiral molecule as possible starting element of complex chiral systems
Caglioti, L., & Pályi, G. (2013) · RENDICONTI LINCEI · doi:10.1007/s12210-013-0227-3 · Cited by 9
Self-citationAsymmetric Autocatalysis and the Origins of Homochirality of Organic Compounds. An Overview
Soai, K., Matsumoto, A., & Kawasaki, T. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00001-0 · Cited by 8
Romagnoli, C., Sieng, B., & Amedjkouh, M. (2020) · Chirality · doi:10.1002/chir.23256 · Cited by 7
Kurdi, R., Táborosi, A., Zucchi, C., & Pályi, G. (2014) · Symmetry · doi:10.3390/sym6030551 · Cited by 6
Self-citationKawasaki, T., Matsumoto, A., Sato, I., & Soai, K. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00008-3 · Cited by 5
Gridnev, I. D. (2014) · Journal of Synthetic Organic Chemistry Japan · doi:10.5059/yukigoseikyokaishi.72.1250 · Cited by 5
Chiral selectivity vs. noise in spontaneous mirror symmetry breaking
Hochberg, D., Buhse, T., Micheau, J. C., & Ribó, J. M. (2023) · Physical Chemistry Chemical Physics · doi:10.1039/d3cp03311b · Cited by 4
Kinetic and Structural Aspects of Mirror-Image Symmetry Breaking in the Soai Reaction
Buhse, T., Noble‐Terán, M. E., Cruz, J., Micheau, J. C., & Coudret, C. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00004-6 · Cited by 4
Érdi, P., & Lente, G. (2014) · Springer series in synergetics · doi:10.1007/978-1-4939-0387-0_3 · Cited by 2
Structural Study of Asymmetric Autocatalysis by X-Ray Crystallography
Matsumoto, A., Kawasaki, T., & Soai, K. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00010-1 · Cited by 2
Absolute Asymmetric Synthesis and the Origin of Biological Chirality
Lente, G. (2012) · Cellular origin and life in extreme habitats · doi:10.1007/978-94-007-2941-4_27 · Cited by 1
Model Equivalency in Interpreting the Stochastic Enantiomer Distribution in the Soai Reaction
Lente, G. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00009-5 · Cited by 1
(2019) · Elsevier eBooks · doi:10.1016/b978-0-12-812212-9.16001-4
Matsumoto, A., Kawasaki, T., & Soai, K. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00273
Isotope Chirality and Cosmochemistry
Barabás, B., Kurdi, R., Maioli, M., & Pályi, G. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00075
Self-citationStochastic Modeling of Asymmetric Autocatalysis in the Soai Reaction
Lente, G. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00179
Metadata
- Authors
- Barabas, B., Caglioti, L., Zucchi, C., Maioli, M., Gál, E., Micskei, K., & Pályi, G.
- Affiliations
- Department of Stochastics, University of Technology and Economics, Müegyetem rkp. 3(H), H-1111 Budapest, Hungary, Department of Chemistry and Technology of Biologically Active Compounds, University “La Sapienza”−Roma, P.le A. Moro 5, I-00185 Roma, Italy, Department of Chemistry, University of Modena and Reggio Emilia, Via Campi 183, I-41100 Modena, Italy, Department of Mathemathics, University of Modena and Reggio Emilia, Via Campi 213, I-41100 Modena, Italy, and Institute of Inorganic and Analytical...
- University of Modena and Reggio Emilia (IT)
- Corresponding author
- Pályi, Gyula
- Venue
- The Journal of Physical Chemistry B
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-09-12
- Volume
- 111
- Issue
- 39
- Pages
- 11506-11510
- ISSN
- 1520-5207 (ISSN-L)
- 1520-6106
- OpenAlex
- W2064752480
- Cited by
- 45
- References
- 35
- Citations by year
- 2023: 1 · 2022: 4 · 2021: 2 · 2020: 1 · 2019: 2 · 2018: 1 · 2017: 5 · 2016: 3 · 2015: 3 · 2014: 4 · 2013: 1 · 2012: 2
- FWCI
- 2.59
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Physical Chemistry B (publishedVersion)
- PubMed (publishedVersion)
- University of Debrecen Electronic Archive (University of Debrecen) (submittedVersion)
- IRIS UNIMORE (University of Modena and Reggio Emilia) (submittedVersion)
- IRIS Research product catalog (Sapienza University of Rome) (submittedVersion)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Analytical Chemistry › Analytical Chemistry and Chromatography
- Keywords
- Soai reaction, enantiomeric excess, non-Gaussian distributions, distribution symmetry, enantioselectivity
- MeSH terms
- Catalysis, Models, Chemical, Stereoisomerism, Models, Statistical
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review