NMR Studies of Drugs. Applications of a Chiral Lanthanide Shift Reagent to Methoxamine in Chloroform-d or Acetonitrile-d 3.

DeArment, Michael; Eastabrooks, Michelle; Venkatasubban, K. S.; Benshafrut, Ronnie; Rothchild, Robert; Wyss, Helen

doi:10.1080/00387019408007258

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1998

2018

Publication Types

Select...

Article3

Other1

Book1

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 5 publications

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

References

2018

Differentiation of Chiral Compounds Using NMR Spectroscopy

View full text Add to dashboard Cite

References

2018

Differentiation of Chiral Compounds Using NMR Spectroscopy

View full text Add to dashboard Cite

Chiral Derivatizing Agents, Macrocycles, Metal Complexes, and Liquid Crystals for Enantiomer Differentiation in NMR Spectroscopy

Wenzel

2013

Topics in Current Chemistry

View full text Add to dashboard Cite

Enantiomerically pure chiral auxiliary agents are often used in NMR spectroscopy to facilitate the differentiation of enantiomers. Chiral derivatizing agents are covalently bound to the substrate and differences in chemical shifts of the resulting diastereomeric complexes are used in the analysis. Macrocycles such as cyclodextrins, crown ethers, and calix[4]resorcinarenes are chiral solvating agents that associate with the substrate through non-covalent interactions. Enantiomeric differentiation occurs in the NMR spectrum because of the diastereomeric nature of the associated complexes and/or because of the differences in association constants between the two enantiomers and the chiral reagent. Metal complexes are Lewis acids that bind to suitable Lewis base donor compounds. Exchange of substrate can be slow or fast depending on the particular metal ion, mimicking the behavior of a chiral derivatizing or solvating agent, respectively. Chiral liquid crystals undergo a partial alignment in an applied magnetic field and enantiomers dissolved in the liquid crystal undergo a partial alignment as well. If the alignment of the two enantiomers is different, enantiomeric differentiation can potentially be observed by differences in chemical shifts, differences in dipolar coupling constants, and different magnitudes of splitting of quadrupolar nuclei such as deuterium. The chiral reagents described herein can be used to determine enantiomeric composition and sometimes to assign absolute configuration. Significant discoveries as well as recent findings with each of these types of systems are described.

show abstract

Using NMR spectroscopic methods to determine enantiomeric purity and assign absolute stereochemistry

Wenzel

Chisholm

2011

Progress in Nuclear Magnetic Resonance Spectroscopy

158

View full text Add to dashboard Cite

NMR Studies of Drugs. Applications of a Chiral Lanthanide Shift Reagent to Methoxamine in Chloroform-d or Acetonitrile-d ₃.

Abstract: The 'H NMR spectra of racemic (erythro) methoxamine free base, I, ~-(l-aminoethyl)-2,5-dimethoxybenzenemethanol, have been studied at or near ambient temperatures in CDC1, or CD3CN with the added chiral lanthanide shift reagent ( L S R ) , tris[3-(heptaf luoropropylhydroxymethylene) -(+) -

Cited by 5 publications

References 13 publications

References

References

Chiral Derivatizing Agents, Macrocycles, Metal Complexes, and Liquid Crystals for Enantiomer Differentiation in NMR Spectroscopy

Using NMR spectroscopic methods to determine enantiomeric purity and assign absolute stereochemistry

Contact Info

Product

Resources

About