The anomeric effect on the basis of natural bond orbital analysis

2013 ◽  
Vol 11 (17) ◽  
pp. 2885 ◽  
Author(s):  
Matheus P. Freitas
Keyword(s):  
Natural Bond Orbital ◽  
Natural Bond Orbital Analysis ◽  
Anomeric Effect ◽  
Orbital Analysis

Component analysis of the X-C-Y anomeric effect (X = O, S; Y = F, OMe, NHMe) by DFT molecular orbital calculations and natural bond orbital analysis

2006 ◽  
Vol 84 (4) ◽  
pp. 692-701 ◽  
Author(s):  
Melissa L Trapp ◽  
Jonathan K Watts ◽  
Noham Weinberg ◽  
B Mario Pinto
Keyword(s):  
Molecular Orbital ◽  
Electrostatic Interactions ◽  
Natural Bond Orbital ◽  
Component Analysis ◽  
Natural Bond Orbital Analysis ◽  
Molecular Orbital Calculations ◽  
Orbital Interaction ◽  
Anomeric Effect ◽  
Dft Molecular Orbital Calculations ◽  
Orbital Analysis

Six 2-Y-substituted oxacyclohexane and thiacyclohexane heterocycles (Y = F, OMe, NHMe) were examined using DFT molecular orbital calculations. Natural bond orbital (NBO) analysis of the total energy behaviour yielded the orbital-interaction factors contributing to the conformational equilibria. The dipole moments of the optimized systems were used to estimate the electrostatic contributions to the anomeric effect. The primary determinant of the X-C-Y anomeric effect was found to be the orbital interaction components associated with the combined endo- and exo-anomeric effects acting in concert in the axial conformers. Electrostatic interactions made a contribution to the observed conformer stabilization in all cases, but did not account for the relative magnitudes of the energy differences among conformers of homologous molecules. In the case of the methylamino substituent, accentuated steric interactions in the axial conformer precluded stabilization by the exo-anomeric interaction and consequently, the net endo/exo anomeric stabilization did not dominate the conformational equilibria.Key words: anomeric effect, component analysis, natural bond orbital analysis, electrostatic, steric, and orbital interaction effects.

Conformational Stabilization of 1,3-Benzodioxole:  Anomeric Effect by Natural Bond Orbital Analysis

2001 ◽  
Vol 105 (13) ◽  
pp. 3221-3225 ◽  
Author(s):  
Seongho Moon ◽  
Younghi Kwon ◽  
Jaebum Lee ◽  
Jaebum Choo
Keyword(s):  
Natural Bond Orbital ◽  
Natural Bond Orbital Analysis ◽  
Anomeric Effect ◽  
Orbital Analysis ◽  
Conformational Stabilization

scholarly journals Energy, orbital and structural stacking landscape of a purine homodimer system

2020 ◽  
Vol 139 (10) ◽  
Author(s):  
Tomasz Sierański
Keyword(s):  
Potential Energy ◽  
Intermolecular Interactions ◽  
Potential Energy Surfaces ◽  
Natural Bond Orbital ◽  
Natural Bond Orbital Analysis ◽  
Energy Sources ◽  
Energy Decomposition ◽  
Energy Surfaces ◽  
Orbital Analysis ◽  
Insight Into

Abstract The multidimensional study, combining the extensive calculations of potential energy surfaces for the parallel-displaced configurations and methods such as energy decomposition and natural bond orbital analysis, has been carried out. The resulted data give an energy, orbital and structural landscapes of this biologically essential system. The balance of the two energy sources, electrostatic and dispersion, is clearly visible. The obtained results, taken as a whole, provide an insight into the hierarchy of intermolecular interactions in the purine system, together with their sources.

The role of hyperconjugation in the unusual conformation of thymine: A natural bond orbital analysis

2018 ◽  
Vol 1130 ◽  
pp. 58-62 ◽  
Author(s):  
Emerson Rengifo ◽  
Sara Gómez ◽  
Julio C. Arce ◽  
Frank Weinhold ◽  
Albeiro Restrepo
Keyword(s):  
Natural Bond Orbital ◽  
Natural Bond Orbital Analysis ◽  
Orbital Analysis

Competitive resonance at the carbonyl group as visualized by the natural bond orbital analysis

1997 ◽  
Vol 435 (2) ◽  
pp. 123-132 ◽  
Author(s):  
Bernd Kallies ◽  
Erich Kleinpeter ◽  
Andreas Koch ◽  
Rolf Mitzner
Keyword(s):  
Carbonyl Group ◽  
Natural Bond Orbital ◽  
Natural Bond Orbital Analysis ◽  
Orbital Analysis
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