The conformers of 2-bromocyclohexanone
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Molecular modeling and biological evaluation of 2-N,N- dimethylaminecyclohexyl 1-N′,N′-dimethylcarbamate isomers and their methylsulfate salts as cholinesterases inhibitors
2010, Journal of Molecular StructureCitation Excerpt :The individual steps are well described in the literature. Cyclohexanone was reacted with bromine to obtain 2-bromocyclohexanone [21], which was placed in an autoclave with N,N-dimethylamine solution to give 2-N,N-dimethylaminecyclohexanone [22]. Reduction of this ketone with lithium aluminum hydride [23] gave a mixture of cis and trans (25:75) 2-N,N-dimethylaminecyclohexanol, which were subsequently reacted with N,N-dimethylcarbamyl chloride [24] to obtain the cis an trans-2-N,N-dimethylaminocyclohexyl 1-N′,N′-dimethylcarbamate (compounds 1 and 2).
The case of infrared carbonyl stretching intensities of 2-bromocyclohexanone: Conformational and intermolecular interaction insights
2010, Chemical Physics LettersCitation Excerpt :Using this approach and the MP2-based results, the intermolecular interaction for the equatorial–equatorial dimer is 3.7 kcal mol−1 more attractive than for the most stable axial–axial dimer. This result alone does not guarantee that 2-bromocyclohexanone self-associates; however, Allinger and Allinger [1] determined in the past that the molecular weight of 2-bromocyclohexanone in cyclohexane is 2.7 times larger than the corresponding value for the monomer (176 g mol−1), suggesting self-association. Also, the stronger self-association in the equatorial–equatorial dimer is supported by DFT frequency calculations: while the CO vibration mode oscillates independently for each unit of the axial–axial dimer 8 (1687 cm−1 for unit A and 1691 cm−1 for unit B), the equatorial–equatorial dimer 23 exhibits symmetric and asymmetric CO stretchings (νs = 1698 cm−1 and νa = 1703 cm−1), showing the interrelationship between the units.
Octa-O-propanoyl-β-maltose: crystal structure, acyl stacking, related structures, and conformational analysis
2007, Carbohydrate ResearchCitation Excerpt :Of course, dipole–dipole stabilization of carbonyl groups is well known. The molecule 2-bromocyclohexanone forms stacked clusters, the size of which depends on the concentration and dielectric constant of the solvent,11 and acetone dimers occur in the vapor phase.12 Allen et al.13 found that 15% of all crystals of compounds that contain carbonyl groups have non-bonded C⋯O distances of less than 3.6 Å between carbonyl groups.
Conformational analysis and stereoelectronic effects in trans-1,2-dihalocyclohexanes: <sup>1</sup>H NMR and theoretical investigation
2005, Spectrochimica Acta - Part A: Molecular and Biomolecular SpectroscopyStructural characterization of two novel potential anticholinesterasic agents
2003, Journal of Molecular Structure