Distinguishing diastereomeric organic compounds based on the concerted use of3J(C,H) and3J(N,H) values

Gröger, Stefan; Josey, John A.; Poppe, Leszek

doi:10.1002/(sici)1097-458x(199910)37:10<748::aid-mrc541>3.0.co;2-m

Cited by 3 publications

(2 citation statements)

References 16 publications

(11 reference statements)

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“…A more reliable solution for the assignment is the use of additional, heteronuclear, vicinal coupling constants such as 13 C-H, 31 P-H, 19 F-H, 15 N-H [23,24,25,26,27]. The rotamer populations have to be estimated from both the H-H and the heteronuclear coupling constants according to the two kinds of assignment.…”

Section: Obtaining Vicinal Coupling Constantsmentioning

confidence: 99%

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Kraszni

Szakács²,

Noszál³

2004

Analytical and Bioanalytical Chemistry

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Methods to determine rotamer populations from NMR homo- and heteronuclear vicinal coupling constants are reviewed. Theory and practice related to the elucidation of various gauche and trans limiting coupling constants as key parameters in the characterization of discrete rotational isomers are discussed. Properties and capacities of Karplus-type equations are assessed. Continuous models of rotational isomerism are compared to discrete ones. Principles of the highly specific physicochemical parameters rotamer-specific basicity and rotamer-specific partition coefficient are also described.

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Section: Obtaining Vicinal Coupling Constantsmentioning

confidence: 99%

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Kraszni

Szakács²,

Noszál³

2004

Analytical and Bioanalytical Chemistry

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“…The authors note that their technique does not always lead to an unambiguous answer. 56 Yabuuchi and Kusumi presented a method of determining the absolute con¢guration of sulfoxides by derivatization ¢rst by amination to a sulfoximine, then by reaction with methoxyphenylacetic acid at the nitrogen. The one-pot derivatization is followed by 1 H NMR of the puri¢ed diastereomers.…”

Section: Determination Of Stereochemistry or Enantiopuritymentioning

confidence: 99%

12 NMR Spectroscopic methods

Halkides

McClure

2000

Annu. Rep. Prog. Chem., Sect. B

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Modern proton‐detected 1D ¹H–¹⁵N NMR experiments. Application to the measurement of ¹H,¹⁵N coupling constants at natural abundance

Parella

Belloc

2001

Magnetic Reson in Chemistry

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Non-selective and selective versions of several proton-detected 1D NMR experiments to be applied to 15 N are proposed. Clean, artifact-free 1D spectra are easily obtained by the effective coherence selection by pulsed-field gradients and the attainable sensitivity is maximized using modern pulse schemes. Despite the low sensitivity inherent to 15 N NMR spectroscopy, the successful application of these experiments is demonstrated for resonance assignments and accurate measurement of both one-bond and long-range proton-nitrogen coupling constants on a model tripeptide at natural abundance.

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Distinguishing diastereomeric organic compounds based on the concerted use of3J(C,H) and3J(N,H) values

Cited by 3 publications

References 16 publications

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

12 NMR Spectroscopic methods

Modern proton‐detected 1D ¹H–¹⁵N NMR experiments. Application to the measurement of ¹H,¹⁵N coupling constants at natural abundance

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Distinguishing diastereomeric organic compounds based on the concerted use of3J(C,H) and3J(N,H) values

Cited by 3 publications

References 16 publications

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

12 NMR Spectroscopic methods

Modern proton‐detected 1D 1H–15N NMR experiments. Application to the measurement of 1H,15N coupling constants at natural abundance

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Modern proton‐detected 1D ¹H–¹⁵N NMR experiments. Application to the measurement of ¹H,¹⁵N coupling constants at natural abundance