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Crystals
Special Issues
Advances in Chiral Crystallization, Resolution and Deracemization
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Advances in Chiral Crystallization, Resolution and Deracemization

A special issue of Crystals (ISSN 2073-4352). This special issue belongs to the section "Industrial Crystallization".

Deadline for manuscript submissions: closed (25 May 2022) | Viewed by 6960

Special Issue Editors

Dr. Xiouras Christos

E-Mail Website
Guest Editor
Crystallization Technology Unit (CTU), Janssen Research & Development, Janssen Pharmaceutical Companies of Johnson & Johnson, Tournhoutseweg 30, 2340 Beerse, Belgium
Interests: industrial crystallization; chiral crystallization and deracemization; (bio)pharmaceutical manufacturing; crystal engineering; thermodynamic and kinetic process modeling; process monitoring and control; polymorphism and crystal transformations; process intensification
Dr. René Steendam

E-Mail Website
Guest Editor
Ardena Amsterdam B.V., Meibergdreef 31, 1105 AZ Amsterdam, The Netherlands
Interests: chiral resolution and deracemization; solid state chemistry; synthetic organic chemistry; crystal nucleation; industrial crystallization; continuous crystallization
Prof. Dr. Joop H. ter Horst

E-Mail Website
Guest Editor
UFR des Sciences et Techniques, Laboratoire SMS-EA3233, Universite de Rouen Normandie, Place Emile Blondel, 76821 Mont-Saint-Aignan, France
Interests: industrial crystallization fundamentals; crystal nucleation; chiral separation and deracemization; continuous crystallization; separation technology
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Ever since Louis Pasteur observed the rotatory effect of chiral crystals of sodium ammonium tartrate using plane-polarized light in 1848, the concept of chirality and its far-reaching implications never ceased to astonish us. Chiral objects, be it molecules, supramolecules or crystals, all share the same property: they are distinguishable (non-superimposable) from their mirror image. It is now well appreciated that this subtle but ubiquitous geometric property can tremendously influence the functional and biological properties of drugs and materials with implications not only in chemistry and biology, but also in other fields such as physics, pharmacy and material science.

Properties unique to enantiomers tend to manifest themselves predominantly in the solid/crystalline state. The latter fact, coupled with the difficulty to obtain single enantipure compounds through solution-phase chemistry, has led us to pay special attention to chiral solid-state properties. Such solid state properties can be utilized to obtain enantiopure compounds, through the development of crystallization methods for chiral resolution.

Recently, we have witnessed an outstanding development on both experimental and theoretical frameworks which have significantly advanced out understanding of supramolecular chirality and chiral crystallization, giving rise not only to an increased understanding of the fundamental aspects and origins of homochirality, but also to the development of novel, highly efficient chiral crystallization, resolution and deracemization processes.

This Special Issue of Crystals is devoted to collecting state-of-the-art contributions on a broad range of topics related to solid-state chirality, crystallization, resolution and deracemization including, but not limited to, the following:

  • Processes to obtain pure enantiomers/diastereomers: diastereomeric (classical) resolution, preferential crystallization (entrainment), total spontaneous resolution, deracemization including Viedma ripening, enantiospecific co-crystallization, preferential enrichment, resolution via salt/complex formation, sublimation, and hybrid processes, among others.
  • Solution/solid phase thermodynamics of chiral systems: properties and energetics of chiral systems, phase diagrams, crystal structures of chiral compounds, polymorphism and phase transformations, racemization/epimerization processes, conformational chirality, chiral discrimination, recognition and symmetry breaking, among others.
  • Monitoring, modelling and control of chiral crystallization: Novel (process) analytical (high throughput) techniques for monitoring/characterization of chiral compounds, crystal nucleation, growth, dissolution and aggregation of chiral compounds, mathematical modelling and simulation of chiral crystallization, resolution and deracemization processes, and industrial design of (continuous) chiral resolution processes, among others.

Dr. Xiouras Christos
Dr. René Steendam
Prof. Joop H. ter Horst
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Crystals is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2600 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • chiral crystallization and resolution
  • deracemization
  • preferential crystallization
  • thermodynamics and phase diagrams
  • supramolecular chirality
  • enantiomers and diastereomers
  • crystal growth and nucleation
  • polymorphism and crystal structure
  • racemization and epimerization
  • chiral amplification and mirror symmetry breaking

Published Papers (3 papers)

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Research

13 pages, 2583 KiB  
Article
Crystalline State Hydrogen Bonding of 2-(2-Hydroxybenzylidene)Thiazolo[3,2-a]Pyrimidines: A Way to Non-Centrosymmetric Crystals
by Artem S. Agarkov, Igor A. Litvinov, Elina R. Gabitova, Alexander S. Ovsyannikov, Pavel V. Dorovatovskii, Andrey K. Shiryaev, Svetlana E. Solovieva and Igor S. Antipin
Crystals 2022, 12(4), 494; https://0-doi-org.brum.beds.ac.uk/10.3390/cryst12040494 - 02 Apr 2022
Cited by 6 | Viewed by 1925
Abstract
Thiazolopyrimidines are attractive to medical chemists as new antitumor agents due to their high inhibiting activity towards the tumor cells replication process and easy modification of their structure by varying of the number and nature of substituents. The presence of asymmetric C5 carbon [...] Read more.
Thiazolopyrimidines are attractive to medical chemists as new antitumor agents due to their high inhibiting activity towards the tumor cells replication process and easy modification of their structure by varying of the number and nature of substituents. The presence of asymmetric C5 carbon atoms requires the development of racemic mixture separation procedures for these heterocycles. One of the more effective ways is the crystallization of a racemic compound as a conglomerate. A prerequisite for such separation is the formation of non-centrosymmetric crystals presenting Sohncke space groups. For the construction of chiral supramolecular ensembles in a crystalline state, hydrogen bonds were chosen as supramolecular synthons. In this context, salicylic derivatives at the C2 atom of thiazolopyrimidines were synthesized. The crystal structures of the obtained compounds were established by SCXRD. The regularities of the solvent’s influence on the crystal packaging were revealed. The conditions for the preparation of crystals with the chiral space group due to intermolecular hydrogen bonds were discovered. Full article
(This article belongs to the Special Issue Advances in Chiral Crystallization, Resolution and Deracemization)
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14 pages, 4844 KiB  
Article
A Simple Population Balance Model for Crystallization of L-Lactide in a Mixture of n-Hexane and Tetrahydrofuran
by Tam Le Minh, Thao Phan Thanh, No Nguyen Thi Hong and Vuong Phan Minh
Crystals 2022, 12(2), 221; https://0-doi-org.brum.beds.ac.uk/10.3390/cryst12020221 - 02 Feb 2022
Cited by 2 | Viewed by 2019
Abstract
In this contribution, crystallization was performed to assess the kinetics of nucleation and crystal growth of L-lactide. In most common solvents, this compound shows very high solubility even at low temperatures, which could be challenging for crystallization process design. In the first part [...] Read more.
In this contribution, crystallization was performed to assess the kinetics of nucleation and crystal growth of L-lactide. In most common solvents, this compound shows very high solubility even at low temperatures, which could be challenging for crystallization process design. In the first part of this paper, the anti-solvent effects of n-hexane on solutions of L-lactide in tetrahydrofuran (THF) were investigated through studying the influence of solvent compositions on the solubility. Thanks to these effects, the solubility of the interested compound can be adjusted to desired degrees of supersaturation by adding suitable amounts of the anti-solvent. In the second part, a solvent composition at a mass ratio of 45/55 (n-hexane/THF) was chosen, and an isothermal seeded crystallization process was implemented. The evolution of the particle sizes and changes in the solute concentration profile of this process were monitored. Based on the obtained data, a widely used model, i.e., the population balance equation (PBE), was then utilized to model the crystal size distribution (CSD). Reasonable assumptions were made to reduce the mathematical complexity of the PBE. In the simplified model, only crystal growth and secondary nucleation were considered for model formulation, with assumptions of the size-independent growth rate and negligible size of nuclei. The kinetic parameters were estimated by using the seed and final-time crystal density functions in combination with variations in the concentration of the mother liquor. Indeed, the numerical solution for the one-dimensional problem of the L-lactide crystallization based on the estimated parameters gained a relatively good agreement with the determined CSD. Furthermore, the obtained model also correlated well with the variations in the solute concentration of the mother liquor. In short, this simple approach can be used for predicting the productivity and CSD of the L-lactide crystallization. Full article
(This article belongs to the Special Issue Advances in Chiral Crystallization, Resolution and Deracemization)
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5 pages, 1129 KiB  
Communication
Resolution of a Metastable Racemic Compound of Anhydrous Phencyphos by Hydrate Formation
by Michel Leeman and Richard M. Kellogg
Crystals 2021, 11(10), 1225; https://0-doi-org.brum.beds.ac.uk/10.3390/cryst11101225 - 12 Oct 2021
Viewed by 1781
Abstract
The resolution of 2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide (phencyphos) was achieved by dissolution of anhydrous racemic phencyphos, a racemic compound, accompanied by simultaneous secondary nucleation of the dissolved racemate on to enantiopure seeds of phencyphos hydrate, a conglomerate. The seeds were placed in separate compartments and [...] Read more.
The resolution of 2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide (phencyphos) was achieved by dissolution of anhydrous racemic phencyphos, a racemic compound, accompanied by simultaneous secondary nucleation of the dissolved racemate on to enantiopure seeds of phencyphos hydrate, a conglomerate. The seeds were placed in separate compartments and the pure enantiomers could be conveniently collected from these compartments after the dissolution of the anhydrous racemate. Full article
(This article belongs to the Special Issue Advances in Chiral Crystallization, Resolution and Deracemization)
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