Spectroscopic enantiodifferentiation of chiral molecules in the gas phase

Latini, Andrea; Toja, Daniela; Giardini-Guidoni, A.; Palleschi, Antonio; Piccirillo, S.; Speranza, Maurizio

doi:10.1002/(sici)1520-636x(1999)11:5/6<376::aid-chir5>3.3.co;2-v

Cited by 13 publications

(18 citation statements)

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“…These shifts are larger than those found for the sec-butyl alcohols. The red shift of the E R A S heterochiral complex (∆ν = −161 cm −1 ) exceeds that of the homochiral one (∆ν = −144 cm −1 ) by 17 cm −1 in agreement with other cases [4]. In the 1cR2PI mass spectral patterns, strong signals at m/e= 74 ([A R(S) H] + ), corresponding to the dissociative proton transfer (DPT), are observed.…”

Section: Figure 1 1cr2pi Mass Resolved Excitation Spectra Of Complexsupporting

confidence: 86%

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Photochemical R2PI study of chirality and intermolecular forces in supersonic beam

Guidoni

Piccirillo

Scuderi

et al. 2001

International Journal of Photoenergy

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Abstract. One and two-color, mass selected R2PI spectra of the S 1 ← S 0 transitions in the bare (+)-(R)-have been recorded after a supersonic molecular beam expansion. The one-color R2PI excitation spectra of the diastereomeric complexes are characterized by significant shifts of their band origin relative to that of bare E R . The extent and the direction of these spectral shifts are found to depend upon the structure and the configuration of solv and are attributed to different short-range interactions in the ground and excited states of the complexes. In analogy with other diastereomeric complexes, the phenomenological binding energy of the homochiral cluster is found to be greater than that of the heterochiral one. Preliminary measurements of excitation spectrum of (+)-(R)-1-Indanol (I R ) is also reported.

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Section: Figure 1 1cr2pi Mass Resolved Excitation Spectra Of Complexsupporting

confidence: 86%

“…These studies gave insights into the attractive and repulsive forces operating in these systems, and it was found that the homochiral complexes are more stable than the heterochiral ones [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Photochemical R2PI study of chirality and intermolecular forces in supersonic beam

Guidoni

Piccirillo

Scuderi

et al. 2001

International Journal of Photoenergy

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“…To investigate the role of fluorine substitution in the chiral recognition process, we investigated the structure and the vibronic spectra of the adducts of FE R with R-and S-2-aminobutane (A R/S ) and compared them with previous results 122,123 obtained for complexes of its nonfluorinated analogues.…”

Section: Supramolecular Diastereomersmentioning

confidence: 99%

Molecular and supramolecular chirality: R2PI spectroscopy as a tool for the gas‐phase recognition of chiral systems of biological interest

et al. 2008

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Dedicated to Professor Domenico Misiti on the occasion of his 75th birthday. ABSTRACTIn life sciences, diastereomeric chiral molecule/chiral receptor complexes are held together by a different combination of intermolecular forces and are therefore endowed with different stability and reactivity. Determination of these forces, which are normally affected in the condensed phase by solvent and supramolecular interactions, can be accomplished through the generation of diastereomeric complexes in the isolated state and their spectroscopic investigation. This review presents a detailed discussion of the mass resolved Resonant Two Photon Ionization (R2PI-TOF) technique in supersonic beams and introduces an overview of various other technologies currently available for the spectroscopic study of gas phase chiral molecules and supramolecular systems. It reports case studies primarily from our recent work using R2PI-TOF methodology for chiral recognition in clusters containing molecules of biological interest. The measurement of absorption spectra, ionization and fragmentation thresholds of diastereomeric clusters by this technique allow the determination of the nature of the intrinsic interactions, which control their formation and which affect their stability and reactivity.

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“…The quantification was done by measuring the relative peak intensity of the complexes in mass spectrometer [40 -47]. Speranza applied ESI-MS n CID and REMPI-TOF methodologies to measure the fragmentation thresholds of diastereomeric clusters [19,23,25,32,48,49]. They found that the chiral recognition was very sensitive to cavity size and hydrophilic/hydrophobic properties of the chiral receptor [24,50].…”

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confidence: 99%

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Cong

Czerwieniec

McJimpsey

et al. 2006

J. Am. Soc. Mass Spectrom.

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Gas-phase zwitterionic amino acids were formed in complexes of underivatized ␤-cyclodextrin through reactions with a neutral base, n-propylamine. The reaction was performed in the analyzer cell of an electrospray ionization-Fourier transform mass spectrometer. Most of the natural amino acids were studied with three cyclodextrin hosts including ␣-, ␤-, and ␥-cyclodextrin to understand better the structural features that lead to the stabilization of the zwitterionic complexes. Molecular dynamics calculations were performed to provide insight into the structural features of the complexes. The rate constants of the reactions were obtained through kinetic plots. Examination of both L-and D-enantiomers of the amino acid showed that the reaction was enantioselective. The reaction was then employed to analyze mixtures of Glu enantiomers naturally occurring in the bacteria Bacillus licheniformis. (J Am Soc Mass Spectrom 2006, 17, 442-452)

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Spectroscopic enantiodifferentiation of chiral molecules in the gas phase

Cited by 13 publications

References 0 publications

Photochemical R2PI study of chirality and intermolecular forces in supersonic beam

Photochemical R2PI study of chirality and intermolecular forces in supersonic beam

Molecular and supramolecular chirality: R2PI spectroscopy as a tool for the gas‐phase recognition of chiral systems of biological interest

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

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