Journal
JOURNAL OF PHYSICAL CHEMISTRY A
Volume 117, Issue 50, Pages 13673-13679Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp407671m
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Funding
- Deutsche Forschungsgemeinschaft
- Land Niedersachen
- Spanish MICINN
- MINECO [CTQ2011-22923, CTQ2012-39132-CO2-02]
- Basque Government [IT520-10, UPV/EHU (UFI11/23]
- MICINN
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The conformational and structural properties of the bicyclic quinolizidine alkaloid (-)-lupinine have been investigated in a supersonic jet expansion using microwave spectroscopy. The rotational spectrum is consistent with a single dominant trans conformation within a double-chair skeleton, which is stabilized by more than 10.4 kJ mol(-1) with respect to other conformations. In the isolated conditions of the jet, the hydroxy methyl side chain of the molecule locks in to form an intramolecular O-H...N hydrogen bond to the electron lone pair at the nitrogen atom. Accurate rotational constants, centrifugal distortion corrections, and N-14 nuclear quadrupole coupling parameters are reported and compared to ab initio (MP2) and DFT (M06-2X) calculations. The stability of lupinine is further compared computationally with epilupinine and decaline in order to gauge the influence of intramolecular hydrogen bonding, absent in these molecules.
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