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

The structure and clustering propensity of a chiral derivative of -1,2-cyclohexanediol, namely, 1-phenyl- -1,2-cyclohexanediol ( -PCD), has been studied under supersonic expansion conditions by combining laser spectroscopy with quantum chemistry calculations. The presence of the phenyl substituent i...

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Bibliographic Details
Published in:Physical chemistry chemical physics : PCCP 2024-04, Vol.26 (14), p.10610-10621
Main Authors: Dupont, Jennifer, Hartwig, Beppo, Le Barbu-Debus, Katia, Lepere, Valeria, Guillot, Regis, Suhm, Martin A, Zehnacker, Anne
Format: Article
Language:English
Subjects:
Chemical Sciences
Clustering
Dimers
Diols
Molecular structure
Physics
Quantum chemistry
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Summary:The structure and clustering propensity of a chiral derivative of -1,2-cyclohexanediol, namely, 1-phenyl- -1,2-cyclohexanediol ( -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 -1,2-cyclohexanediol ( -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 -PCD relative to -1,2-cyclohexanediol ( -CD), which shows heterochiral preference, is explained by the presence of the phenyl substituent rather than the effect of isomerism. Indeed the transiently chiral -CD also forms preferentially heterodimers, whose structure is very close to that of the corresponding -CD dimer.
ISSN:1463-9076
1463-9084
DOI:10.1039/d4cp00351a