Issue 14, 2024

Homochiral vs. heterochiral preference in chiral self-recognition of cyclic diols

Abstract

The structure and clustering propensity of a chiral derivative of cis-1,2-cyclohexanediol, namely, 1-phenyl-cis-1,2-cyclohexanediol (cis-PCD), has been studied under supersonic expansion conditions by combining laser spectroscopy with quantum chemistry calculations. The presence of the phenyl substituent induces conformational locking relative to cis-1,2-cyclohexanediol (cis-CD), and only one conformer of the bare molecule is observed by both Raman and IR-UV double resonance spectroscopy. The homochiral preference inferred for the dimer formation at low enough temperature is in line with the formation of a conglomerate in the solid state. The change in clustering propensity in cis-PCD relative to trans-1,2-cyclohexanediol (trans-CD), which shows heterochiral preference, is explained by the presence of the phenyl substituent rather than the effect of cis-trans isomerism. Indeed the transiently chiral cis-CD also forms preferentially heterodimers, whose structure is very close to that of the corresponding trans-CD dimer.

Graphical abstract: Homochiral vs. heterochiral preference in chiral self-recognition of cyclic diols

Supplementary files

Article information

Article type
Paper
Submitted
25 1月 2024
Accepted
08 3月 2024
First published
12 3月 2024
This article is Open Access
Creative Commons BY-NC license

Phys. Chem. Chem. Phys., 2024,26, 10610-10621

Homochiral vs. heterochiral preference in chiral self-recognition of cyclic diols

J. Dupont, B. Hartwig, K. Le Barbu-Debus, V. Lepere, R. Guillot, M. A. Suhm and A. Zehnacker, Phys. Chem. Chem. Phys., 2024, 26, 10610 DOI: 10.1039/D4CP00351A

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