Por favor, use este identificador para citar o enlazar a este item:
http://hdl.handle.net/10261/272953
COMPARTIR / EXPORTAR:
SHARE CORE BASE | |
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Título: | Unusually high pyramidal geometry of the bicyclic amide nitrogen in a complex 7-azabicyclo[2.2.1]heptane derivative: Theoretical analysis using a bottom-up strategy |
Autor: | Alemán, Carlos; Jiménez, Ana I. CSIC ORCID; Cativiela, Carlos CSIC ORCID; Pérez, Juan J.; Casanovas, Jordi | Fecha de publicación: | 2005 | Editor: | American Chemical Society | Citación: | Journal of Physical Chemistry B 109(23): 11836-11841 (2005) | Resumen: | The high pyramidalization of the bicyclic amide nitrogen found in the crystal structure of a dipeptide incorporating (1S,2S,4R)-N-benzoyl-2-phenyl-7-azabicyclo[2.2.1]heptane-1-carboxylic acid has been investigated using quantum mechanical calculations. More specifically, a bottom-up strategy based on the study of model molecules of progressive complexity has been used. First, an appropriate quantum mechanical method has been selected by examining the distortion of the amide bond in three simple model molecules. Next, the amide distortion induced by the norbornane ring has been evaluated by considering three different 7-azabicyclo[2.2.1]heptane amides. After this, the suitability of quantum mechanical calculations to predict the effect of the substituents on the pyramidalization of the bicyclic amide nitrogen has been investigated by comparing experimental and theoretical parameters for a number of compounds. Finally, the factors responsible for amide distortion in the (1S,2S,4R)-N-benzoyl-2-phenyl-7-azabicyclo[2.2.1]heptane-1-carboxylic acid derivative have been elucidated using a hierarchical approach. For this purpose, several derivatives were generated by removing or modifying the substituents attached to the 7-azanorbornane system. Results have been discussed in terms of intramolecular specific interactions. | Versión del editor: | https://doi.org/10.1021/jp050141t | URI: | http://hdl.handle.net/10261/272953 | DOI: | 10.1021/jp050141t | ISSN: | 1520-6106 |
Aparece en las colecciones: | (ICMA) Artículos |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
---|---|---|---|---|
accesoRestringido.pdf | 59,24 kB | Adobe PDF | Visualizar/Abrir |
CORE Recommender
SCOPUSTM
Citations
11
checked on 05-may-2024
WEB OF SCIENCETM
Citations
10
checked on 22-feb-2024
Page view(s)
44
checked on 07-may-2024
Download(s)
11
checked on 07-may-2024
Google ScholarTM
Check
Altmetric
Altmetric
NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.