Structural study of 3-methyl-3-azabicyclo[3.2.1]octan-8α(and β)-ols by ab initio calculations, NMR and IR spectroscopy
A stereoselective synthesis of 3-methyl-3-azabicyclo[3.2.1]octan-8α(and β)-ols (I and II) has been carried out. Compounds I and II have been studied by 1H, 13C NMR, NOE 1D experiments, IR spectroscopy and ab initio calculations. These compounds (I and II) adopt in CDCl3 a preferred chair-envelope co...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2003 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/243720 |
| Acceso en línea: | http://hdl.handle.net/10261/243720 |
| Access Level: | acceso abierto |
| Palabra clave: | 3-methyl-3-azabicyclo[3.2.1]octan-8α(and β)-ols Infrared spectroscopy NMR spectroscopy Conformational analysis Ab initio calculations |
| Sumario: | A stereoselective synthesis of 3-methyl-3-azabicyclo[3.2.1]octan-8α(and β)-ols (I and II) has been carried out. Compounds I and II have been studied by 1H, 13C NMR, NOE 1D experiments, IR spectroscopy and ab initio calculations. These compounds (I and II) adopt in CDCl3 a preferred chair-envelope conformation with the N–CH3 group in equatorial position. Intermolecular associations were deduced by IR and ab initio calculations. The infrared spectra in the ν(O–H) region of compounds I and II were compared with the spectra theoretically calculated at the B3LYP/6-311G** level. Good agreement between the experimental observations and the theoretical calculations has been found. |
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