Noncovalent interactions and odd-even effect control the high-pressure crystal structures of phenyl alcohols.

Authors

Joanna Grelska, Roman Gajda, Joanna Krzeszczakowska, Changyong Park, Krzysztof Woźniak, Wojciech A Sławiński

Published in

IUCrJ. Nov 01, 2026. Epub Nov 01, 2026.

Abstract

We report four high-pressure crystal structures of a homologous series of phenyl alcohols starting with benzyl alcohol, C₆H₅(CH₂)_nOH (n = 1-4). Results were obtained using synchrotron and laboratory single-crystal X-ray diffraction supported by powder diffraction and periodic density functional theory calculations. For three alcohols, 2-phenylethanol, 3-phenyl-1-propanol and 4-phenyl-1-butanol, these represent the first crystal structures of the pure compounds. All structures are characterized by hydrogen-bonded chains of O-H...O interactions, complemented by stabilizing C-H...π and C-H...O contacts. Despite similarities in local bonding motifs, distinct packing arrangements emerge depending on molecular chain length. Even alcohols (n = 2, 4) adopt closely related layered structures with efficient packing, whereas odd analogs (n = 1, 3) exhibit less dense and more asymmetric arrangements. High pressure induces crystallization under 1 GPa, highlighting the role of pressure in accessing otherwise undiscovered crystal forms.

PMID:
42985937
Bibliographic data and abstract were imported from PubMed on 05 Nov 2026.

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