3-Fluoro-2,4-dioxa-7-aza-3-phosphadecalin 3-Oxides as Rigid Acetylcholine Mimetics: Conformational Analysis and Direct Evidence of the Anomeric Effect

2006 ◽  
Vol 89 (7) ◽  
pp. 1351-1366 ◽  
Author(s):  
Stefan Furegati ◽  
Martin Binder ◽  
Anthony Linden ◽  
Peter Rüedi
Keyword(s):  
Conformational Analysis ◽  
Direct Evidence ◽  
Anomeric Effect

The role of the generalized anomeric effect in the conformational analysis of 1,3-dioxacycloalkanes. Conformational analysis of 3,5-dioxabicyclo[5.1.0]octanes and 3,5,8-trioxabicyclo[5.1.0]octanes

1977 ◽  
Vol 42 (2) ◽  
pp. 365-368 ◽  
Author(s):  
Michael H. Gianni ◽  
Robert Cody ◽  
Mohan R. Asthana ◽  
Karl Wursthorn ◽  
Patrick Patanode ◽  
...  
Keyword(s):  
Conformational Analysis ◽  
Anomeric Effect

scholarly journals Salt effects on the conformational behavior of 5-substituted 1,3-dioxanes

2003 ◽  
Vol 75 (5) ◽  
pp. 589-599 ◽  
Author(s):  
Eusebio Juaristi ◽  
G. A. Rosquete-Pina ◽  
M. Vázquez-Hernández ◽  
A. J. Mota
Keyword(s):  
Conformational Analysis ◽  
Metal Ions ◽  
Electrostatic Interactions ◽  
Inorganic Salts ◽  
Conformational Behavior ◽  
Anomeric Effect ◽  
Biological Processes ◽  
Polar Substituents ◽  
Derivatives Of

Since their introduction by E. L. Eliel nearly four decades ago, derivatives of 1,3-dioxane have proved useful in conformational analysis. Examples are discussed, where 5-polar substituents permit the evaluation of fundamental phenomena such as attractive and repulsive gauche effects, electrostatic interactions, and stereoelectronic effects. By the same token, 2-substituted 1,3-dioxanes, 1,3-dithianes, and 1,3-oxathianes are useful frameworks for the study of the anomeric effect and the associated structural and spectroscopic manifestations, such as the so-called Perlin effects. In view of the varied and essential involvement of metal ions and inorganic salts in biological processes, 5-substituted 1,3-dioxanes are presently being examined in the presence of Li+, Na+, K+, Ag+, Mg2+, Ca2+, Ba2+, and other cations, with the aim to increase the understanding of biomolecular properties in vivo.

Conformational analysis of 2-substituted methylenecyclohexanes and 3-substituted cyclohexenes and the anomeric effect

1977 ◽  
Vol 55 (6) ◽  
pp. 1015-1023 ◽  
Author(s):  
Jean Lessard ◽  
Phan Viet Minh Tan ◽  
Robert Martino ◽  
John K. Saunders
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Double Bond ◽  
Magnetic Resonance ◽  
Conformational Analysis ◽  
Methoxy Group ◽  
Anomeric Effect ◽  
Magnetic Resonance Data ◽  
Electronegative Substituent ◽  
Axial Conformer ◽  
Resonance Data

The analysis of the 13C and 1H nuclear magnetic resonance data of 2-substituted methylenecyclohexanes and 3-substituted cyclohexenes demonstrates that a double bond stabilizes the axial conformer for an electronegative substituent. Introduction of a methoxy group on the double bond further increases the relative stability of the axial conformer. These results are interpreted in terms of the 'double bond – no bond' resonance.

On the nature of the anomeric effect in XHn—CH2—OH systems, with X = F, O, N, C

1992 ◽  
Vol 70 (2) ◽  
pp. 604-611 ◽  
Author(s):  
F. Grein ◽  
P. Deslongchamps
Keyword(s):  
Conformational Analysis ◽  
Lone Pair ◽  
Anomeric Effect ◽  
Bond Forming

Using geometry optimizations at the 6-31G** level, energies, bond distances, and charges were obtained for systems XHn—CH2—OH with X = F, O, N, C, for various rotational conformers of the OH group. Conformational analysis shows that systems with X = F and O receive anomeric stabilization due to a partial π-bond forming in the CH2—OH fragment of the molecule, amplified or diminished by lone pair repulsion (or dipole) energies. For the systems with N and C, no π-bond stabilization is found. However, the e-NH2—CH2—OH system is still stabilized due to favourable lone pair repulsion circumstances. Keywords: anomeric effect, abinitio studies, π-bonding model.

Sign in / Sign up

Export Citation Format

Share Document