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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Simultaneously resolving BINOL and proline using a stoichiometric cocrystal switch.

Sarita Songsermsawad¹, Oleksii Shemchuk², Koen Robeyns²

¹Energy Science and Engineering, Vidyasirimedhi Institute of Science and Technology, 555 Moo 1, Payupnai, Wang Chan, Rayong, 21210, Thailand. adrian.flood@vistec.ac.th.

Chemical Communications (Cambridge, England)

|May 29, 2024

Summary

This summary is machine-generated.

Stoichiometry controls the formation of racemic compounds versus conglomerates when mixing two racemates. Adjusting the ratio of binol and proline allows a reversible switch between these solid forms, enabling simultaneous resolution.

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Area of Science:

Crystallization Science
Chiral Chemistry
Solid-State Chemistry

Background:

Cocrystal formation is crucial for resolving racemates.
Controlling solid-state structures is essential for separation processes.
Simultaneous resolution of multiple chiral compounds presents unique challenges.

Purpose of the Study:

To investigate the role of stoichiometry in simultaneous cocrystal resolution.
To explore the reversible switching between racemic compounds and conglomerates.
To demonstrate this phenomenon using the binol and proline racemates.

Main Methods:

Stoichiometric control of reactant ratios (1:2 and 2:1 for binol:proline).
Cocrystallization experiments.
Solid-state characterization techniques (e.g., powder X-ray diffraction, DSC).

Main Results:

A 1:2 stoichiometry of binol:proline yielded a racemic compound.
A 2:1 stoichiometry of binol:proline resulted in conglomerate formation and simultaneous resolution.
Reversible switching between racemic compound and conglomerate was achieved by manipulating stoichiometry.

Conclusions:

Stoichiometry is a critical factor for achieving simultaneous cocrystal resolution.
The binol-proline system demonstrates a novel, stoichiometry-driven reversible switch between solid forms.
This study pioneers the investigation of such behavior involving two distinct racemates.