DFT calculations of the anomeric and exo-anomeric effect of the hydroperoxy and peroxy groups

Kośnik, Wioletta; Bocian, Wojciech; Chmielewski, Marek; Tvaroŝka, Igor

doi:10.1016/j.carres.2008.03.032

Cited by 15 publications

(3 citation statements)

References 28 publications

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“…To the best of our knowledge, there is no reported theoretical study on anomeric effect in X-Y-CH 2 -Z molecule with Y representing carbene (C:), despite that numerous anomeric units have been studied [1][2][3][4][5][6][7][8][9][10][11][12]. Carbenes are neutral compounds featuring a divalent carbon atom possessing one lone pair of electrons, and with only six electrons in its valence shell [13].…”

Section: Introductionmentioning

confidence: 99%

“…Currently, the anomeric effect is generally recognized as being of more importance for acyclic molecules containing the X-Y-CH 2 -Z moiety, where Y is an atom bearing at least one lone pair of electrons and Z is an electronegative atom [2][3][4][5]. The gauche conformer is preferred to the anti conformer, irrespective of the nature of the electronegative group, Z.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical study on the anomeric effect in carbene compound XC:CH2F (X=CH3, NH2, OH)

Liu

Yuan

et al. 2010

Journal of Molecular Structure: THEOCHEM

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Theoretical study on the anomeric effect in carbene compound XC:CH2F (X=CH3, NH2, OH)

Liu

Yuan

et al. 2010

Journal of Molecular Structure: THEOCHEM

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“…The silly but convenient names "chair" and "boat" came later.) Moreover, from this type of compounds valuable information on the structural point of view has been reported [8][9][10][11][12]. Furthermore, the conformational analysis of these compounds is particularly well developed [13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Computational evaluation concerning the deviation of the atoms in 1- and 4-postions on the six-member ring and the effects on 1HNMR chemical shift

et al. 2011

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Density functional theory (DFT) calculations were carried out on some cyclohexane derivatives to investigate the deviation atoms on the 1-and 4-positions of chair plane. The deviations of chair plane of two position in the cyclohexane derivatives were calculated at the B3LYP/6-31 ++ G(d,p) level. Furthermore, we investigated the correlation between deviations of two positions from chair plane on the chemical shift hydrogen atoms on the 4-position.

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Anomeric and rotameric preferences of glucopyranose in vacuo, water and organic solvents

Karabulut

Leszczyński

2013

J Mol Model

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Glucopyranose is the most stable form of glucose in solution. Identification of molecular structure of glucopyranose is very important because of its biological and synthetic significance; it is not an easy task because of the large number of possible configurations. Relative energies of exocyclic hydroxymethyl rotamers and α-β anomers of D-glucopyranose have been determined at the reference MP2/6-31G(d,p) level geometry by ab initio calculations at the infinite basis set limit of MP2 approach and with inclusion of CCSD(T) correction term evaluated with the aug-cc-pVDZ basis set in vacuum, water, dimethylsulfoxide, tetrahydrofurane and ethanol. The infinite basis set limit of MP2 level was determined by two point extrapolation using aug-cc-pVTZ and aug-cc-pVQZ basis sets. Solvent effects, relative energies and binding energies have been considered applying explicit calculations and implicit solvent models.

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DFT calculations of the anomeric and exo-anomeric effect of the hydroperoxy and peroxy groups

Cited by 15 publications

References 28 publications

Theoretical study on the anomeric effect in carbene compound XC:CH2F (X=CH3, NH2, OH)

Theoretical study on the anomeric effect in carbene compound XC:CH2F (X=CH3, NH2, OH)

Computational evaluation concerning the deviation of the atoms in 1- and 4-postions on the six-member ring and the effects on 1HNMR chemical shift

Anomeric and rotameric preferences of glucopyranose in vacuo, water and organic solvents

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