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.
Integrity signals
Registry
Cites
Statistics
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]
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 · see citing works
Absolute Asymmetric Synthesis: A Commentary
Mislow, K. (2003) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc20030849 · Cited by 286 · see citing works
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 · see citing works
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 · see citing works
Kawasaki, T., Suzuki, K., Shimizu, M., Ishikawa, K., & Soai, K. (2006) · Chirality · doi:10.1002/chir.20273 · Cited by 109 · see citing works
Flagged first, then by citations
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 · see citing works
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 · see citing works
Schiaffino, L., & Ercolani, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802450 · Cited by 100 · see citing works
Ercolani, G., & Schiaffino, L. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo102525t · Cited by 86 · see citing works
Gridnev, I. D., & Vorobiev, A. K. (2012) · ACS Catalysis · doi:10.1021/cs300497h · Cited by 84 · see citing works
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 · see citing works
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 · see citing works
Dóka, É., & Lente, G. (2011) · Journal of the American Chemical Society · doi:10.1021/ja207408y · Cited by 60 · see citing works
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 · see citing works
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 · see citing works
Self-citationElucidation 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 · see citing works
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 · see citing works
Self-citation
- 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
- 5
- 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 › Spectroscopy › 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