Principal component analysis of long-range ‘W’ coupling constants of some cyclic compounds

Constantino, Maurício Gomes; Lacerda, Valdemar; Silva, Gil Valdo José da; Tasić, Ljubica; Rittner, Roberto

doi:10.1016/s0022-2860(01)00591-9

Cited by 30 publications

(27 citation statements)

References 3 publications

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“…Moreover, we found that there is a relation between these 4 J HH values and the calculated dihedral angle between the corresponding hydrogens. 7,8 More recently, we have reported the detailed assignment of 1 H and 13 C NMR spectral data for various cyclopentanes. 9 In continuation of these studies, we began an investigation of the heteronuclear 2,3 J CH spin-spin couplings in some cyclopentane derivatives to verify their potential utility as a tool for determining the stereochemistry of substituents in these rings.…”

Section: Introductionmentioning

confidence: 99%

Long‐range J_CH heteronuclear coupling constants in cyclopentane derivatives

Lacerda

Silva

Constantino

et al. 2005

Magnetic Reson in Chemistry

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Section: Introductionmentioning

confidence: 99%

Long‐range J_CH heteronuclear coupling constants in cyclopentane derivatives

Lacerda

Silva

Constantino

et al. 2005

Magnetic Reson in Chemistry

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“…Moreover, we found that there is a relation between these 4 J HH values and the calculated dihedral angle between the corresponding hydrogens. [8,9] In this field, we also reported the detailed assignment of 1 H and 13 C NMR spectral data for cyclopentanes 1-7b (Fig. 2).…”

Section: Stereochemistry Of Cyclopentane Derivatives From 23 J Ch Dementioning

confidence: 91%

Stereochemistry of cyclopentane derivatives from ^{2, 3}J_CH dependence on dihedral angle (θ HCCX)

Lacerda

Silva

Constantino

et al. 2008

Magnetic Reson in Chemistry

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The (2,3)J(CH) dependence on dihedral angle (theta H--C--C--X) for cyclopentane derivatives was investigated. We observed that the combined use of experimentally obtained (2,3)J(CH) values and the theoretically determined dihedral angles between the corresponding nuclei can be used to infer the relative stereochemistry of the ring substituents in cyclopentane derivatives. There is a good correlation between the magnitude of (3)J(CH) and the dihedral angle between the hydrogen and the coupled carbon (R2 = 0.88).

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“…Absence of ''W'' coupling is known for molecules containing bulky substituents capable of interacting with the ''W'' protons. [25] In Fig. 4, the experimental raw spectrum of longifolene C is compared with the simulated spectra B and A derived by calculation of conformations 1A and 1B.…”

Section: Coupling Constant Analysismentioning

confidence: 99%

Conformational Analysis of Longifolene

Subramaniam

Patel

Karimi

2008

Spectroscopy Letters

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We describe the stable conformation of the tricyclic sesquiterpenoid, longifolene, by experimental NMR data and molecular mechanics calculations of the coupling constants. The flexible seven-membered ring of longifolene adopts a twist-chair conformation. Analysis of the coupling constants, particularly of the methylene protons in the cycloheptane ring moiety, agrees with this low-energy conformation. Low-temperature NMR experiments and nuclear Overhauser effect measurements indicate that there is a single exchange-averaged NMR spectrum that has the highest population of the most stable conformer.

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Principal component analysis of long-range ‘W’ coupling constants of some cyclic compounds

Cited by 30 publications

References 3 publications

Long‐range J_CH heteronuclear coupling constants in cyclopentane derivatives

Long‐range J_CH heteronuclear coupling constants in cyclopentane derivatives

Stereochemistry of cyclopentane derivatives from ^{2, 3}J_CH dependence on dihedral angle (θ HCCX)

Conformational Analysis of Longifolene

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Principal component analysis of long-range ‘W’ coupling constants of some cyclic compounds

Cited by 30 publications

References 3 publications

Long‐range JCH heteronuclear coupling constants in cyclopentane derivatives

Long‐range JCH heteronuclear coupling constants in cyclopentane derivatives

Stereochemistry of cyclopentane derivatives from 2, 3JCH dependence on dihedral angle (θ HCCX)

Conformational Analysis of Longifolene

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Product

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About

Long‐range J_CH heteronuclear coupling constants in cyclopentane derivatives

Long‐range J_CH heteronuclear coupling constants in cyclopentane derivatives

Stereochemistry of cyclopentane derivatives from ^{2, 3}J_CH dependence on dihedral angle (θ HCCX)