2002
DOI: 10.1039/b204635k
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Conformational analysis of 2-halocyclohexanones: an NMR, theoretical and solvation study

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Cited by 48 publications
(50 citation statements)
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“…The calculated MP2/aug-cc-pVDZ energy difference (E eq -E ax ) between the two conformers in the isolated state is 2.1 kcal mol −1 , which is in agreement with the experimental value; this energy difference decreases with increasing the medium polarity. [2] The H 2 -C-C-H 3 dihedral angle in the equatorial conformer is close to 180…”
Section: Resultsmentioning
confidence: 97%
“…The calculated MP2/aug-cc-pVDZ energy difference (E eq -E ax ) between the two conformers in the isolated state is 2.1 kcal mol −1 , which is in agreement with the experimental value; this energy difference decreases with increasing the medium polarity. [2] The H 2 -C-C-H 3 dihedral angle in the equatorial conformer is close to 180…”
Section: Resultsmentioning
confidence: 97%
“…2-Halocarbonyl [83][84][85][86] and 2-thiocarbonyl [84,87] compounds show pronounced biases for axial conformers in some systems (Scheme 22). For example, 2-(phenylthio)cyclohexanone prefers the axial conformer 77, presumably to maximize overlap of σ C-S with π* of the carbonyl group.…”
Section: Comparisons Between Substituted Oxocarbenium Ions and Ketonesmentioning
confidence: 98%
“…In addition, the conformational preferences of mono and di-haloacetones have been extensively studied through both theoretical and spectroscopic tools [7][8][9], though a detailed description of the stereoelectronic effects involved in the equilibrium is not given. The axial and equatorial preferences of 2-substituted-cyclohexanones have been attributed to classical interactions, solvent effects and to a hyperconjugation between lone pair of substituent and the vacant C=O* orbital [10][11][12]. Nevertheless, despite the conformational equilibration for the haloketones has been fully determined, the governing factors involved are not completely understood and investigated.…”
Section: Introductionmentioning
confidence: 96%