Work

Hydrogen-bond-assisted conformational selection of picaridin in the gas phase

Year: 2025

Type: article

Abstract: Understanding the intrinsic shape of bioactive molecules such as picaridin is key to elucidating their mode of action. In this work, we characterize the gas-phase conformational landscape of picaridin, a flexible chiral repellent with two stereocenters. Broadband rotational spectroscopy combined with quantum chemical calculations reveals a single dominant conformer per enantiomeric pair, both stabilized by internal O-H⋯O hydrogen bonds. These intramolecular interactions induce conformational locking, constraining the hydroxyethyl chain and favouring a compact geometry. Non-covalent interaction analysis further confirms that dispersion and hydrogen bonding play a central role in conformational selection under isolated conditions.

Source: Physical Chemistry Chemical Physics

DOI: 10.1039/d5cp02108a

Authors: Otger Crehuet, Andrea Vázquez, Francisco J. Basterretxea, Pablo Pinacho, Emilio J. Cocinero

Institutions: University of the Basque Country, Instituto Biofisika, Universidad de Valladolid

Language: English

Topic: Molecular Spectroscopy and Structure

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid