2026-04-28T21:19:12Zhttps://uvadoc.uva.es/oai/request

oai:uvadoc.uva.es:10324/769932025-09-04T11:44:26Zcom_10324_1186com_10324_931com_10324_894col_10324_1404

Hydrogen-Bond-Assisted Conformational Selection of Picaridin in the Gas Phase Crehuet, Otger Vázquez, Andrea Basterretxea, Francisco Jose Pinacho Morante, Pablo Cocinero, Emilio J. Producción Científica 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. 2025-07-30T09:38:33Z 2025-07-30T09:38:33Z 2025 info:eu-repo/semantics/article Physical Chemistry Chemical Physics, junio 2025, vol. 27, p. 15222-15227 1463-9076 https://uvadoc.uva.es/handle/10324/76993 10.1039/D5CP02108A 15222 15227 Physical Chemistry Chemical Physics 27 1463-9084 eng https://pubs.rsc.org/en/Content/ArticleLanding/2025/CP/D5CP02108A info:eu-repo/semantics/openAccess Royal Society of Chemistry SI