Chirality Transfer in a Methyl Lactate–Ammonia Complex Observed by Matrix‐Isolation Vibrational Circular Dichroism Spectroscopy

Merten, Christian; Xu, Yunjie

doi:10.1002/anie.201208685

Cited by 51 publications

(35 citation statements)

References 39 publications

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“…Diffraction methods [46,47] 18. Matrix isolation/vibrational circular dichroism [11,48] of sequential IR photons, dynamic energy flow within the IRMPD process is an important consideration [50]. Figure 1 provides a schematic representation of the IRMPD process.…”

Section: Infrared Multiple Photon Dissociation (Irmpd)mentioning

confidence: 99%

Determining the properties of gas-phase clusters

Hopkins

2015

Molecular Physics

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As our understanding of clusters has improved, we have found that rather than being models for surface and condensed phase phenomena, clusters often display chemical and physical properties that are quite distinct from those of their atomic constituents or associated bulk materials. Indeed, identifying and utilising the unique properties of dimensionally confined species is a major theme in nanotechnology. Consequently, numerous experimental and computational methods have been employed to investigate the structures and properties of cluster systems. In this article, the techniques of infrared multiple photon dissociation and differential mobility spectrometry are discussed using the examples of [Ag·B 12 F 12 ] − and tetraalkylammonium/solvent ionic clusters, respectively.

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Section: Infrared Multiple Photon Dissociation (Irmpd)mentioning

confidence: 99%

Determining the properties of gas-phase clusters

Hopkins

2015

Molecular Physics

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“…9 VCD spectroscopy measures the differential absorbance of left-and right-circular polarized light during vibrational transitions of chiral molecules. 29 In the focus of the present study is one of the structurally simplest chiral amines available from the chiral pool, namely a-phenylethyl amine (PEA, Fig. [11][12][13] Furthermore, VCD spectroscopy has been shown to be a very powerful technique to study intermolecular interactions such as solutesolvent [14][15][16][17] or solute-solute [18][19][20][21][22] interactions as well as chirality transfer phenomena.…”

Section: Introductionmentioning

confidence: 99%

Conformational distortion of α-phenylethyl amine in cryogenic matrices – a matrix isolation VCD study

Pollok

Merten

2016

Phys. Chem. Chem. Phys.

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The chiral amine α-phenylethyl amine (PEA) was isolated in cryogenic matrices and investigated using vibrational circular dichroism (VCD) and infrared spectroscopy. The potential energy surface (PES) of PEA features five different conformers connected by relatively low conformational transition states. Based on the IR spectra, it could be confirmed that all conformational energy barriers are passed at a deposition temperature of 20 K, and that only the global minimum conformation of PEA is populated in both argon and nitrogen matrices. However, differences in the calculated and experimental VCD spectra indicate deviations from the minimum structure by perturbation of the phenyl ring as well as of the amine orientation. The degree of the perturbation is found to also depend on the choice of the host gas, which shows the subtle influence of the environment on the conformational distortion of PEA.

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“…Fori nstance,c hiral oxiranes in water were found to induce aVCD signal for the H 2 Obending modes, [14] and more recently,a mmonia was shown to become optically active upon interacting with methyl lactate under matrixisolation conditions. [15] Furthermore,chiral induction in an ion pair has been reported by Bas et al [16] This encouraged us to apply VCD spectroscopy to study chirality-induction phenomena in ion-pair-based asymmetric catalysis with the focus on establishing structure-spectra relationships which can be used to predict catalytic selectivity.…”

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confidence: 98%

Stereochemical Communication within a Chiral Ion Pair Catalyst

et al. 2015

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Ionic interactions are increasingly appreciated as a key, asymmetry-inducing factor in enantioselective catalytic transformations, including those involving Brønsted acid or base catalysis, phase-transfer catalysis, and related processes. However, a detailed understanding of these interactions is often lacking. Herein, we show how an enantiopure anion enforces a chiral conformation onto a catalytically relevant achiral cation. Specifically, we use vibrational circular dichroism (VCD) spectroscopy to monitor the transmission of stereochemical information from a chiral phosphate anion to a flexible manganese(III)-salen cation. We show that VCD can be used to study solvent effects and that the obtained chiroptical data directly and quantitatively correlate with the experimentally observed enantioselectivity in an asymmetric olefin epoxidation reaction.

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Chirality Transfer in a Methyl Lactate–Ammonia Complex Observed by Matrix‐Isolation Vibrational Circular Dichroism Spectroscopy

Cited by 51 publications

References 39 publications

Determining the properties of gas-phase clusters

Determining the properties of gas-phase clusters

Conformational distortion of α-phenylethyl amine in cryogenic matrices – a matrix isolation VCD study

Stereochemical Communication within a Chiral Ion Pair Catalyst

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