Skip to main content
SpringerLink
Log in

The strange case of achiral compounds which were reported to always crystallize in the same chiral group

  • Review Article
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

In the present review, one of the mysteries of chemistry, the non-stochastic preference for one enantiomer during crystallization processes, is discussed with some examples of the literature and one published by our own group.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Azeroual S, Surprenant J, Lazzara TD, Kocun M, Tao Y, Cuccia LA, Lehn JM (2012) Mirror symmetry breaking and chiral amplification in foldamer-based supramolecular helical aggregates. Chem Commun 48:2292–2294

    Article  CAS  Google Scholar 

  2. McLaughlin DT, Nguyen TPT, Mengnjo L, Bian C, Leun YH, Goodfellow E, Ramrup P, Woo S, Cuccia LA (2014) Viedma ripening of conglomerate crystals of achiral molecules monitored using solid-state circular dichroism. Cryst Growth Des 14:1067–1076

    Article  CAS  Google Scholar 

  3. Lennartson A, Håkansson M (2015) Absolute asymmetric synthesis of five-coordinate complexes. New J Chem 39:5936–5943

    Article  CAS  Google Scholar 

  4. Quesada-Moreno MM, Cruz-Cabeza AJ, Avilés-Moreno JR, Cabildo P, Claramunt RM, Alkorta I, Elguero J, Zúñiga FJ, López-González JJ (2017) The curious case of 2-propyl-1H-benzimidazole in the solid state: an experimental and theoretical study. J Phys Chem A 121:5665–5674

    Article  CAS  PubMed  Google Scholar 

  5. Mislow K (2003) Absolute asymmetric synthesis: a commentary. Collect Czechoslov Chem Commun 68:849–864

    Article  CAS  Google Scholar 

  6. Mislow K, Bickart P (1976/1977) An epistemological note on chirality. Isr J Chem 15:1–6

  7. Pályi G, Kurdi R, Zucchi C (2017) Advances in asymmetric autocatalysis and related topics. Academic Press, Elsevier, London

    Google Scholar 

  8. (2007) New frontiers in asymmetric catalysis. In: Mikami K, Lautens M (eds) Wiley, Hoboken

  9. Vestergren M, Johansson A, Lennartson A, Håkansson M (2004) Non-stochastic homochiral helix crystallization: cryptochirality in control? Mendeleev Commun 14:259–260

    Article  CAS  Google Scholar 

  10. Viedma C (2007) Selective chiral symmetry breaking during crystallization: parity violation or cryptochiral environment in control? Cryst Growth Des 7:553–556

    Article  CAS  Google Scholar 

  11. Eliel EL (1997) Infelicitous stereochemical nomenclature. Chirality 9:428–430

    Article  CAS  Google Scholar 

  12. Quesada-Moreno MM, Avilés-Moreno JR, López-González JJ, Jacob K, Vendier L, Etienne M, Alkorta I, Elguero J, Claramunt RM (2017) Supramolecular organization of perfluorinated 1H-indazoles in the solid state using X-ray crystallography, SSNMR and sensitive (VCD) and non sensitive (MIR, FIR and Raman) to chirality vibrational spectroscopies. Phys Chem Chem Phys 19:1632–1643

    Article  CAS  PubMed  Google Scholar 

  13. Jacques J, Collet A, Wilen SH (1994) Enantiomers, racemates, and resolutions. Krieger Publishing Company, Malabar

    Google Scholar 

  14. Ribó JM, Crusats J, Sagués F, Claret J, Rubires R (2001) Chiral sign induction by vortices during the formation of mesophases in stirred solutions. Science 292:2063–2066

    Article  PubMed  Google Scholar 

  15. Arteaga O, Canillas A, El-Hachemi Z, Crusats J, Ribó JM (2015) Structure vs. excitonic transitions in self-assembled porphyrin nanotubes and their effect on light absorption and scattering. Nanoscale 7:20435–20441

    Article  CAS  PubMed  Google Scholar 

  16. Lennartson A, Olssob S, Sundberg J, Håkansson M (2009) A different approach to enantioselective organic synthesis: absolute asymmetric synthesis of organometallic reagents. Angew Chem Int Ed 48:3137–3140

    Article  CAS  Google Scholar 

  17. Avalos M, Babiano R, Cintas P, Jiménez JL, Palacios JC, Barron LD (1998) Absolute asymmetric synthesis under physical fields: facts and fictions. Chem Rev 98:2391–2404

    Article  CAS  PubMed  Google Scholar 

  18. Feringa BL, van Delden RA (1999) Absolute asymmetric synthesis: the origin, control, and amplification of chirality. Angew Chem Int Ed Engl 38:3418–3438

    Article  CAS  PubMed  Google Scholar 

  19. Viedma C (2006) Chiral symmetry breaking during crystallization: complete chiral purity induced by non-linear autocatalysis. Phys Rev Lett 94:065504

    Article  CAS  Google Scholar 

  20. Viedma C, Cintas P (2011) Homochirality beyond grinding: deracemizing chiral crystals by temperature gradient under boiling. Chem Commun 47:12786–12788

    Article  CAS  Google Scholar 

  21. Steendam RRE, Harmsen B, Meekes H, van Enckevort WJP, Kaptein B, Kellogg RM, Raap J, Rutjes FPJT, Vlieg E (2013) Controlling the effect of chiral impurities on Viedma ripening. Cryst Growth Des 13:4776–4780

    Article  CAS  Google Scholar 

  22. Kawasaki T, Suzuki K, Shimizu M, Ishikawa K, Soai K (2006) Spontaneous absolute asymmetric synthesis in the presence of achiral silica gel in conjunction with asymmetric autocatalysis. Chirality 18:479–482

    Article  CAS  PubMed  Google Scholar 

  23. Weissbuch I, Addadi L, Leisetowitz L, Lahav M (1988) Total asymmetric transformations at interfaces with centrosymmetric crystals: role of hydrophobic and kinetic effects in the crystallization of the system glycine/.alpha.-amino acids. J Am Chem Soc 110:561–567

    Article  CAS  Google Scholar 

  24. Lahav M, Weissbuch I, Shavit E, Reiner C, Nicholson GJ, Schurig V (2006) Parity violation energetic difference and enantiomorphous crystals-caveats; reinvestigation of tyrosine crystallization. Orig Life Evol Biosph 36:151–170

    Article  CAS  PubMed  Google Scholar 

  25. Jaakkola S, Sharma V, Annila A (2008) Cause of chirality consensus. Curr Chem Biol 2:153–158

    CAS  Google Scholar 

  26. Plasson R, Brandenburg A (2010) Homochirality and the need for energy. Orig Life Evol Biosph 40:93–110

    Article  Google Scholar 

Download references

Acknowledgements

Computer, storage, and other resources from the CTI (CSIC) are gratefully acknowledged. This publication is dedicated to Professor Meir Lahav for his seminal contributions to this field.

Funding

This work was carried out with financial support from the Ministerio de Economía y Competitividad (Project Nos. CTQ2015-63997-C2-2-P) and Comunidad Autónoma de Madrid (Project Fotocarbon, ref. S2013/MIT-2841).

Author information

Authors and Affiliations

  1. Instituto de Química Médica, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva, 3, E-28006, Madrid, Spain

    Ibon Alkorta & José Elguero

Authors
  1. Ibon Alkorta
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. José Elguero
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ibon Alkorta.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alkorta, I., Elguero, J. The strange case of achiral compounds which were reported to always crystallize in the same chiral group. Struct Chem 30, 633–636 (2019). https://doi.org/10.1007/s11224-018-1276-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-018-1276-0

Keywords

Search

Navigation