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Acids with Chiral Molecules as Essential Organic Compounds of Biogenic–Abiogenic Systems

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Processes and Phenomena on the Boundary Between Biogenic and Abiogenic Nature

Part of the book series: Lecture Notes in Earth System Sciences ((LNESS))

Abstract

The present review generalizes results of a comprehensive experimental study (by means of PXRD, SCXRD, TRPXRD, DSC, IR) of six chiral systems. These are enantiomeric systems of a single substance: (1) the system with a eutectic point (S- and R-E3ClMA), (2) the system forming a binary compound (l- and d-phenylglycine), and (3) the system forming equimolar and non-equimolar discrete compounds (S- and R-malic acid). Also these are diastereomeric systems and a system composed of enantiomers of different substances: (4) the diastereomeric system with continuous solid solutions (l- and l-allo-threonine), and (5) the diastereomeric system with a eutectic point (d- and l-allo-threonine), and (6) the system of enantiomers of different substances (l-valine and l-isoleucine) which contains a non-equimolar discrete compound. Crystal structures of discrete equimolar and non-equimolar homomolecular and heteromolecular compounds found in the systems under discussion are described. Also, polymorph diversity and the limits of solid solutions in such binary systems are discussed.

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Notes

  1. 1.

    The designations represent the relative (l and d) and absolute (S and R) configurations of the levorotatory and dextrorotatory enantiomers, respectively.

  2. 2.

    A chiral center can take place not only at a stereogenic atom, but also in a “space”, for example, in the molecule center of gravity. Not only a chiral center, but also a chiral axis, and a chiral plane can be a source of chirality.

  3. 3.

    The terms “non-equimolar discrete compounds” and “homomolecular” and “heteromolecular discrete compounds” related to chiral compounds were firstly introduced in the papers (Isakov et al. 2015) and (Kotelnikova et al. 2017), respectively.

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Acknowledgements

The investigations were performed using equipment of the Resource Centre for X-ray Diffraction Studies of Saint Petersburg State University and equipment of the MPI Magdeburg PCF lab. The authors thank Dr. N. Taratin, Dr. D. Binev, Dr. S. Muenzberg, Dr. M. G. Krzhizhanovskaya, Prof. A. Seidel-Morgenstern and Prof. G. Coquerel for their contributions over the years. The authors appreciate the financial support provided by the Russian Foundation for Basic Research (Projects: 18-35-00183 mol_a and 16-29-11-727 ofi_m).

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Authors and Affiliations

  1. Saint Petersburg State University, Saint Petersburg, Russia

    Elena N. Kotelnikova, Anton I. Isakov, Lyudmila Yu. Kryuchkova, Andrey A. Zolotarev Jr. & Sergey N. Bocharov

  2. Max Planck Institute for Dynamics of Complex Technical Systems, Magdeburg, Germany

    Heike Lorenz

Authors
  1. Elena N. Kotelnikova
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  2. Anton I. Isakov
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  5. Sergey N. Bocharov
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  6. Heike Lorenz
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Correspondence to Elena N. Kotelnikova .

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Editors and Affiliations

  1. Department of Crystallography, Saint Petersburg State University, Saint Petersburg, Russia

    Olga V. Frank-Kamenetskaya

  2. Department of Botany, Saint Petersburg State University, Saint Petersburg, Russia

    Dmitry Yu. Vlasov

  3. Department of Geochemistry, Saint Petersburg State University, Saint Petersburg, Russia

    Elena G. Panova

  4. Department of Physical Geography and Landscape Planning, Saint Petersburg State University, Saint Petersburg, Russia

    Sofia N. Lessovaia

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Kotelnikova, E.N., Isakov, A.I., Kryuchkova, L.Y., Zolotarev, A.A., Bocharov, S.N., Lorenz, H. (2020). Acids with Chiral Molecules as Essential Organic Compounds of Biogenic–Abiogenic Systems. In: Frank-Kamenetskaya, O., Vlasov, D., Panova, E., Lessovaia, S. (eds) Processes and Phenomena on the Boundary Between Biogenic and Abiogenic Nature. Lecture Notes in Earth System Sciences. Springer, Cham. https://doi.org/10.1007/978-3-030-21614-6_37

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