RT info:eu-repo/semantics/article
T1 Hydrogen-Bond-Assisted Conformational Selection of Picaridin in the Gas Phase
A1 Crehuet, Otger
A1 Vázquez, Andrea
A1 Basterretxea, Francisco Jose
A1 Pinacho, Pablo
A1 Cocinero, Emilio J.
AB 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.
PB Royal Society of Chemistry
SN 1463-9076
YR 2025
FD 2025-06-26
LK https://uvadoc.uva.es/handle/10324/76993
UL https://uvadoc.uva.es/handle/10324/76993
LA eng
NO Physical Chemistry Chemical Physics, junio 2025, vol. 27, p. 15222-15227
NO Producción Científica
DS UVaDOC
RD 01-ago-2025