How Solvent Influences the Anomeric Effect: Roles of Hyperconjugative versus Steric Interactions on the Conformational Preference

2014 ◽  
Vol 79 (4) ◽  
pp. 1571-1581 ◽  
Author(s):  
Changwei Wang ◽  
Fuming Ying ◽  
Wei Wu ◽  
Yirong Mo
Keyword(s):  
Anomeric Effect ◽  
Conformational Preference ◽  
Steric Interactions

Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides

2005 ◽  
Vol 70 (12) ◽  
pp. 2086-2100 ◽  
Author(s):  
Ondřej Vích ◽  
Ladislav Kniežo ◽  
Hana Dvořáková ◽  
Ivan Raich ◽  
Štěpán Valenta
Keyword(s):  
The Other ◽  
Glycosidic Bond ◽  
Conformational Behavior ◽  
Anomeric Effect ◽  
Conformational Preference ◽  
Other Hand ◽  
Conformational Preferences

Conformational behavior of two C-disaccharides, containing D-glucopyranose moiety at the non-reducing end and L- or D-2-deoxy-arabino-hexopyranose moiety at the reducing end, has been studied using MM3 calculations and NMR experiments. The obtained results show that the conformational preference around the C-glycosidic bond is the same in both compounds and corresponds with the exo-anomeric effect. On the other hand, both compounds differ markedly in the conformational arrangement around the C-aglycone bond where the population of conformers is controlled by 1,3-diaxial-like interactions.

Configuration and conformation of alkoxyalkyl and hydroxyalkyl trifluoromethyl nitroxides. Anomeric effects and nitroxide conformations

1981 ◽  
Vol 59 (12) ◽  
pp. 1745-1752 ◽  
Author(s):  
C. Chatgilialoglu ◽  
K. U. Ingold
Keyword(s):  
Anomeric Effect ◽  
Conformational Preference ◽  
Nodal Plane ◽  
Spectral Parameters ◽  
Small Magnitude ◽  
Or Groups ◽  
Steric Factors ◽  
Hyperfine Splittings ◽  
Anomeric Effects ◽  
Configuration And Conformation

The epr spectral parameters for some [Formula: see text] radicals have been measured over a range of temperatures. These radicals are probably non-planar at nitrogen. Their OR groups are in the eclipsed position with respect to the N 2pz orbital, a conformational preference which is attributed to a combination of steric factors and the anomeric effect. For [Formula: see text] the H hyperfine splittings (hfs) are of unusually small magnitude. It is pointed out that all other known [Formula: see text] also have anomalously low H hfs. It is suggested that this is due to the anomeric effect which not only promotes the eclipsed conformation but also causes the OR group to bend towards the semioccupied orbital, thereby moving H and R2 towards the nodal plane of this orbital.

Sulfur-carbon-phosphorus anomeric interactions. 7. Conformational preference of the 2-diphenylphosphinoyl group in 1,3-dioxane. Is there an O-C-P(O) anomeric effect?

1989 ◽  
Vol 54 (22) ◽  
pp. 5191-5193 ◽  
Author(s):  
Eusebio Juaristi ◽  
Abelardo Flores-Vela ◽  
Victoria Labastida
Keyword(s):  
Anomeric Effect ◽  
Conformational Preference

The conformational preference of methoxyl and acetoxyl groups in 3-oxycyclohexenes, 2-oxymethylenecyclohexanes, and 1-oxytetralins and the generalized anomeric effect

1987 ◽  
Vol 65 (8) ◽  
pp. 1761-1768 ◽  
Author(s):  
Adama Ouédraogo ◽  
Minh Tan Phan Viet ◽  
John K. Saunders ◽  
Jean Lessard
Keyword(s):  
Methoxyl Group ◽  
Equatorial Orientation ◽  
Anomeric Effect ◽  
Conformational Preference ◽  
Magnetic Resonance Data ◽  
Conformational Effect ◽  
Axial Conformer ◽  
Resonance Data ◽  
Cis And Trans ◽  
Derivatives Of

The 13C and 1H nuclear magnetic resonance data of 3-oxycyclohexenes, 2-oxymethylenecyclohexanes, and 1-oxytetralins show (i) that the pseudoaxial preference is larger for the acetoxyl group than for the methoxyl group in 3-oxycyclohexenes, (ii) that the methoxyl and the acetoxyl groups have the same pseudoaxial preference in 1-oxytetralins, and (iii) that in 2-oxymethylenecyclohexanes, the acetoxyl group prefers the equatorial orientation whereas the methoxyl group prefers to be axial. These results are interpreted in terms of the orbital picture (π–σ* stabilization of the axial conformer) of the generalized anomeric effect to which is opposed a conformational effect termed the "unsaturation effect" in 2-acetoxymethylenecyclo-hexane and probably also, but to a much smaller extent, in 1-acetoxytetralin. The results also show that cis and transtert-butyl analogues of 3-oxycyclohexenes do not represent the true limit conformers whereas cis and trans 4-tert-butyl derivatives of 2-oxymethylenecyclohexanes do not differ drastically from the limit conformers.

scholarly journals Toward the origin of the conformational preference of 2-methoxyoxane, a model useful to study the anomeric effect

ARKIVOC ◽  
2003 ◽  
Vol 2003 (11) ◽  
pp. 132-148 ◽  
Author(s):  
Karina Martinez ◽  
Fernando Cortes ◽  
Ingrid Leal ◽  
Vanessa Reyna ◽  
Delia Quintana ◽  
...  
Keyword(s):  
Anomeric Effect ◽  
Conformational Preference

The Effect of a Para Substituent on the Conformational Preference of 2,2-Diphenyl-1,3-dioxanes:  Evidence for the Anomeric Effect from X-ray Crystal Structure Analysis1

1999 ◽  
Vol 64 (5) ◽  
pp. 1436-1441 ◽  
Author(s):  
Fumiaki Uehara ◽  
Masayuki Sato ◽  
Chikara Kaneko ◽  
Hiroyuki Kurihara
Keyword(s):  
Crystal Structure ◽  
Anomeric Effect ◽  
Conformational Preference ◽  
X Ray

Conformations and configurations of some chlorosulfated α- and β-D-pentopyranosyl chlorides

1969 ◽  
Vol 47 (7) ◽  
pp. 1157-1162 ◽  
Author(s):  
H. J. Jennings
Keyword(s):  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
Proton Magnetic Resonance ◽  
Proton Magnetic Resonance Spectroscopy ◽  
Resonance Spectroscopy ◽  
Anomeric Effect ◽  
Conformational Preference ◽  
Number Of Factors

The conformations of the fully chlorosulfated α- and β-D-xylopyranosyl and lyxopyranosyl chlorides in deuteriochloroform solution have been studied by proton magnetic resonance spectroscopy. The analysis of the spectra indicated that the anomeric effect is a factor in determining the conformational preference of the pentopyranosyl chlorides, as each existed predominantly in the conformation in which the chlorine was axial. A number of factors involving the synthesis of these chlorides have also been elucidated.

Application of the additivity of group energies to understand conformational preference: the anomeric effect

2010 ◽  
Vol 12 (40) ◽  
pp. 13261 ◽  
Author(s):  
Fernando Cortés-Guzmán ◽  
Jesús Hernández-Trujillo ◽  
Gabriel Cuevas
Keyword(s):  
Anomeric Effect ◽  
Conformational Preference
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