MW SYSTEMATIC STUDY OF ALKALOIDS THE DISTORTED TROPANE

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MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE Patricia Écija Verdejo Spectroscopy

MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE Patricia Écija Verdejo Spectroscopy Group Faculty of Science and Technology University of the Basque Country

Introduction TROPANE ALKALOIDS Solanacease Erythrocylacease tropane 2

Introduction TROPANE ALKALOIDS Solanacease Erythrocylacease tropane 2

Introduction Why are the tropane alkaloids interesting? PHARMACOLOGICAL USES ANTICHOLINERGIC NEUROSTIMULANTS Scopolamine Cocaine NEUROTRANSMISSION

Introduction Why are the tropane alkaloids interesting? PHARMACOLOGICAL USES ANTICHOLINERGIC NEUROSTIMULANTS Scopolamine Cocaine NEUROTRANSMISSION EXPERIMENTS Phenyltropane STRUCTURE-ACTIVITY INTERACT with other compounds NEW PHARMACOLOGICAL compounds 3

Introduction Tropane Alkaloids Theoretical Calculations Rotational Spectroscopy in Supersonic jets ab initio – MP

Introduction Tropane Alkaloids Theoretical Calculations Rotational Spectroscopy in Supersonic jets ab initio – MP 2 DFT methods – B 3 LYP / M 062 X 4

Introduction TROPANE ALKALOIDS TROPINONE MW Spectroscopy 2 k. J mol-1 • X-Ray Difraction Axial

Introduction TROPANE ALKALOIDS TROPINONE MW Spectroscopy 2 k. J mol-1 • X-Ray Difraction Axial • NMR Axial/equatorial EPOXYTROPANES SCOPINE PCCP, 12, 6076, Kristallogr. NCS, 2010 222, 225, 2007 A. S. J. Org. Chem. , 53, 2172, 1988 5

Experimental Set Up Scopine 97% 4 -18 GHz PCCP, 12486, 2010 6

Experimental Set Up Scopine 97% 4 -18 GHz PCCP, 12486, 2010 6

Results Scopine Decomposition Products Scopine ---- Ne Scopine ---- H 2 O Reaction Product

Results Scopine Decomposition Products Scopine ---- Ne Scopine ---- H 2 O Reaction Product Scopine Chem. Phys. Chem. , DOI: 10. 1002/cphc. 201300199, 2013 Scopoline 7

Results Rotational Parameters of Scopoline Chem. Phys. Chem. , DOI: 10. 1002/cphc. 201300199, 2013

Results Rotational Parameters of Scopoline Chem. Phys. Chem. , DOI: 10. 1002/cphc. 201300199, 2013 8

Results No tunnel splitting Chem. Phys. Chem. , DOI: 10. 1002/cphc. 201300199, 2013 >11.

Results No tunnel splitting Chem. Phys. Chem. , DOI: 10. 1002/cphc. 201300199, 2013 >11. 4 k. J mol-1 11. 8 k. J mol-1 (MP 2) 9

IS LASER VAPORIZATION THE SOLUTION? 10

IS LASER VAPORIZATION THE SOLUTION? 10

Ablation FT-MW 355 nm Nd-YAG laser ca. 2 -3 m. J/pulse PCCP, 12486, 2010

Ablation FT-MW 355 nm Nd-YAG laser ca. 2 -3 m. J/pulse PCCP, 12486, 2010 11

Results SCOPINE 12

Results SCOPINE 12

Results Rotational Parameters of Scopine 13

Results Rotational Parameters of Scopine 13

Results Tunnel splitting 6. 25 (1) k. J mol-1 5. 99 k. J mol-1

Results Tunnel splitting 6. 25 (1) k. J mol-1 5. 99 k. J mol-1 (MP 2) 14

Conclusion STRUCTURAL ISOMERIZATION TUNNEL SPLITTING N-Methyl group EQUATORIAL C 6 C 3 N-Methyl group

Conclusion STRUCTURAL ISOMERIZATION TUNNEL SPLITTING N-Methyl group EQUATORIAL C 6 C 3 N-Methyl group AXIAL SCOPINE C 6 SCOPINE Chem. Phys. Chem. , DOI: 10. 1002/cphc. 201300199, 2013 C 3 SCOPOLINE 15

Acknowledgements MW Spectroscopy Group Collaborators Dr. Emilio José Cocinero Montse Vallejo Estíbaliz Méndez Dr.

Acknowledgements MW Spectroscopy Group Collaborators Dr. Emilio José Cocinero Montse Vallejo Estíbaliz Méndez Dr. José A. Fernández Dr. Francisco J. Basterretxea Prof. Fernando Castaño Prof. Alberto Lesarri Prof. Jens-Uwe Grabow Prof. Walther Caminati Prof. Brooks Pate 16

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