1-phenylcyclohexane-1,2-diols and their geometry

Galantay, Eugene

doi:10.1016/s0040-4020(01)98533-3

Cited by 11 publications

(5 citation statements)

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“…The diol forms two weak, but cooperative hydrogen bonds (OH–OH and OH–π) which give rise to separate OH stretching transitions in CCl 4 solution. 66 The water in the monohydrate has several options to attach or insert into this hydrogen bond chain and the most stable conformation is sought. In this particular case, we recommend an extensive search among the possible conformations to identify the global minimum conformation.…”

Section: Molecular Systemsmentioning

confidence: 99%

Setting up the HyDRA blind challenge for the microhydration of organic molecules

Fischer

Bödecker

Zehnacker‐Rentien

et al. 2022

Phys. Chem. Chem. Phys.

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Section: Molecular Systemsmentioning

confidence: 99%

Setting up the HyDRA blind challenge for the microhydration of organic molecules

Fischer

Bödecker

Zehnacker‐Rentien

et al. 2022

Phys. Chem. Chem. Phys.

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“…A stream of oxygen containing ca. 3 % ozone was passed for 25 hr through a solution of (+)-/ra/w-2-phenylcyclohexanecarboxylic acid (1.2 g, 0.006 mol) in acetic acid; 10% H202 (25 ml) was added to the reaction mixture which was then let stand overnight, after which it was evaporated to dryness under reduced pressure with the bath temperature kept below 35°. Precautions against possible explosion were taken.…”

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confidence: 99%

Optically active aromatic chromophores. XI. Circular dichroism studies of some 1-substituted 2-phenylcyclohexanes

Verbit¹,

Price²

1972

J. Am. Chem. Soc.

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A circular dichroism study of the following phenylcyclohexane derivatives has been carried out: (lS,-2R)-( +)-truns-2-phenylcyclohexanol, (1S,2R)-( +)-trans-2-phenylcyclohexylamine, (1S,2S)-( +)-trms-2-phenylcyclohexanecarboxylic acid, (1S,2S)-(+)-trms-2-phenylcyclohexanecarbonyl chloride, (lS,2S)-(+)-rrans-l-hydroxymethyl-2-phenylcyclohexane, (1R,2R)-( -)-cis-2-phenylcyclohexanol, and (1R,2R)-( -)-cis-2-phenylcyclohexyl-amine. The absolute configuration of (+)-trans-2-phenylcyclohexanecarboxylic acid was determined by its oxidation cleavage to (1S,2S)-( +)-truns-l,2-cyclohexanedicarboxylic acid. Variable temperature nmr measurements indicate that the compounds exist almost exclusively in the conformation having the phenyl group equatorial. Infrared hydrogen-bonding studies are reported for the alcohols in the series. The Cotton effects appearing in the 210-220-nm region are considered to be primarily associated with the IL, transition of the aromatic ring. It is proposed that CD Cotton effects due to this transition in appropriate phenyl-containing compounds may be characterized by typical widths at half-height of 10-20 nm. A quadrant rule is formulated for the sign of the 'La Cotton effect in monosubstituted benzene derivatives. hiroptical methods, as Prelog3 terms optical ro-

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“…The OH group contained in TFE might have caused a similar mode mixing problem, 25 but here the coupling to the water OH is sufficiently weak for an unambiguous assignment. This is also the case for PCD, 26 where the monohydrate features a network of three coupled OH oscillators but only one of them shows a strong isotope shift upon 18 O substitution (ESI †).…”

Section: Reference Experimental Valuesmentioning

confidence: 67%