Chiral high-performance liquid chromatographic stationary phases. 1. Separation of the enantiomers of sulfoxides, amines, amino acids, alcohols, hydroxy acids, lactones, and mercaptans

Pirkle, William H.; House, David

doi:10.1021/jo01326a014

Cited by 218 publications

(62 citation statements)

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“…[36][37][38] In some cases, a strong dipole-dipole attraction, such as hydrogen bonding, was involved. The conclusion drawn was further challenged by introducing an additive bearing a polar cyano group, as in acetonitrile, or an electronegative element, such as oxygen (or nitrogen) as in ethyl ether and acetic acid, to the liquid phase.…”

Section: Resultsmentioning

confidence: 99%

Adsorption/Desorption of Pesticidal Carboxylate Esters by Switching Liquid Phases on Humic‐Fraction‐Modified Silica Gel Matrix

Chen

2014

J Chinese Chemical Soc

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A humic-fraction-modified silica gel is prepared and used as the adsorbent for various pesticidal carboxylate esters in hexane. The percentage of adsorption, calculated on the basis of the difference in peak areas for most carboxylate esters in hexane, reaches more than 90% in 1 h. The FTIR (Fourier Transform Infrared) Spectroscopy results show that the interaction force leading to the adsorption observed in hexane is dipole-dipole oriented and is affected negatively both by the steric hindrance created due to the presence of the group near the carbonyl center of esters and the bulky alkyl group attached to an ether linkage. The hydrogen bonding (i.e. strong dipole-dipole interaction) and p-p stacking complexation are either absent or the minor force responsible for the adsorption of carboxylate esters in hexane in most cases. Other factors that cause the variation in the percentage of adsorption include the type of liquid phase (e.g. ethyl ether or acetonitrile vs. hexane) and the additive of acidic or basic origin present in the matrix, which renders the desorption approach for analyte adsorbed.

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Section: Resultsmentioning

confidence: 99%

Adsorption/Desorption of Pesticidal Carboxylate Esters by Switching Liquid Phases on Humic‐Fraction‐Modified Silica Gel Matrix

Chen

2014

J Chinese Chemical Soc

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“…It is followed by a three-member progression built on a 46 cm -1 mode assigned to a torsion of the substituent. The modes which correlate to the 11bi g and 12a1 8 vibrations of the anthracene ring are located at 218 and 390 cm -1 , respectively [11]. Much weaker bands appear at 129 cm -1 in the red of the 08 band, with the same vibrational pattern: hole burning experiments have shown that they are due to other ground-state species, probably a torsion isomer of the molecule (Figs.…”

Section: Bare Moleculementioning

confidence: 88%

“…In these complexes, the geometry is expected to be constrained by a strong interaction related to the presence of a hydrogen bond between the acceptor and the donor. On the other hand, TFAE is known as a chiral resolving agent for chiral phase chromatography: it has been used to discriminate between enantiomers of amines [8], so the study of the nature of the interactions between TFAE and amines can provide information about the nature of the forces responsible for chiral discrimination in these systems.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Electron Transfer in Jet Cooled Molecular Complexes

et al. 1999

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Exciplex and excimer formation have been probed in several jet cooled complexes using mass selective two-photon ionisation and fluorescence excitation spectroscopy as well as ground state depletion spectroscopy (hole burning): (i) In the anthracene-dimethyl-ortho-toluidine system, it has been found that the ionisation step takes place with a much higher efficiency from the charge transfer state responsible for the exciplex emission than from the locally excited state giving rise to the resonant fluorescence. (ii) The dimer, trimer, and higher clusters of anthracene all show only excimer emission. When compared to the dimer, the trimer exhibits a peculiar behaviour (structured fluorescence excitation and hole burning spectra, short lifetime and low ionisation efficiency) which has been related to a significant locally excited character of the initially prepared state of the species excited state. (iii) The influence of an intermolecular hydrogen bond on the electron transfer process has been studied in the 2,2,2-trifluoro-1-(9-anthryl)ethanoldimethylaniline system. A threshold for exciplex formation higher than in the case of the anthracene-dimethylaniline complex is observed.PACS numbers: 31.50. -1-w, 32.30.-r, 33.15.-e, 33.20.-t

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“…The diastereoisomers obtained after chiral derivatizations have been analyzed on a variety of phases [51][52][53][54][55][56][57][58][59], while achirally derivatized carbinols have resolved mainly on polysaccharide-derived CSPs [60][61][62][63] and only few articles reported on the application of Pirkle-type phases for the separation of ethers [64], esters [43,65], carbamates [66][67][68]. To the best of our knowledge, the enantiorecognition of 3,5-dinitro benzoates [65] is the only record in the literature on the resolution of chiral benzyl alcohols as esters of aromatic acids on DNBPG.…”

Section: Introductionmentioning

confidence: 99%

Enantioresolution of a Series of Chiral Benzyl Alcohols by HPLC on a Dinitrobenzoylphenylglycine Stationary Phase after Achiral Pre-Column Derivatization*

Simeonov¹,

Simeonov²,

Todorov³

et al. 2010

AJAC

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High performance liquid chromatography method for the separation of a series of chiral benzyl alcohols on N-(3,5-dinitrobenzoyl)-D-phenylglycine stationary phase (Macherey Nagel, Chiral-2) after pre-column achiral derivatization was developed. Cheap and easy available aromatic acid chlorides were used as derivatization agents. Good to excellent separations of the enantiomers were achieved in all cases in relatively short analytical runs. It was shown that the enantiorecognition depends on the substituents both in the starting alcohol and in the acid chloride. The method presents an efficient alternative to the direct analyses on polysaccharide and cyclodextrine-derived stationary phases.

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Chiral high-performance liquid chromatographic stationary phases. 1. Separation of the enantiomers of sulfoxides, amines, amino acids, alcohols, hydroxy acids, lactones, and mercaptans

Cited by 218 publications

References 0 publications

Adsorption/Desorption of Pesticidal Carboxylate Esters by Switching Liquid Phases on Humic‐Fraction‐Modified Silica Gel Matrix

Adsorption/Desorption of Pesticidal Carboxylate Esters by Switching Liquid Phases on Humic‐Fraction‐Modified Silica Gel Matrix

Photoinduced Electron Transfer in Jet Cooled Molecular Complexes

Enantioresolution of a Series of Chiral Benzyl Alcohols by HPLC on a Dinitrobenzoylphenylglycine Stationary Phase after Achiral Pre-Column Derivatization*

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