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Title: Rotational Spectra of Tetracyclic Quinolizidine Alkaloids: Does a Water Molecule Flip Sparteine?
Authors: Lesarri, Alberto
Pinacho, Ruth
Enríquez, Lourdes
Rubio, José E.
Jaraíz, Martín
Abad, José L.
Gigosos, Marco A.
Issue Date: 2017
Publisher: RSC
Description: Producción Científica
Citation: Physical Chemistry Chemical Physics, 2017, 19, 17473
Abstract: Sparteine is a quinolizidine alkaloid used as chiral auxiliary in asymmetric synthesis. We examine whether hydration by a single molecule can flip sparteine from the most stable trans conformation to the bidentate cis arrangement observed in catalytic complexation to a metal center. Sparteine and the dimer sparteine-water were generated in a supersonic jet expansion with H216O and H218O, and characterized by broadband chirped-pulse microwave spectroscopy. Despite the bidentate water dimer was predicted with larger binding energy, a single isomer was observed for the monohydrated cluster, with sparteine retaining the trans conformation observed for the free molecule. The absence of the bidentate dimer is attributed to kinetic control of the cluster formation, favoring the pre-expansion most abundant monomer. The structural properties of the O-H···N hydrogen bond in the dimer are compared with complexes of other secondary and tertiary amines.
Peer Review: SI
DOI: 10.1039/c7cp01432e
Sponsor: MINECO-FEDER (CTQ2015-68148-C2-2-P)
Publisher Version:
Rights Owner: RSC
Language: eng
Rights: info:eu-repo/semantics/embargoedAccess
Appears in Collections:DEP63 - Artículos de revista

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