A Practical Guide to First-Order Multiplet Analysis in 1H NMR Spectroscopy

Hoye, Thomas R.; Hanson, Paul R.; Vyvyan, James R.

doi:10.1021/jo00094a018

Cited by 65 publications

(42 citation statements)

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“…The signals for 2ЈЈЈ-H to 5ЈЈЈ-H were resolved in CD 3 OD and assigned to glucose. The 13 C NMR spectroscopic data also displayed the expected number of carbons and chemical shifts for glucose, [12] and this was further confirmed by ROESY interactions. The position of the glucose unit was deduced by ROESY experiments, which showed interactions of 1ЈЈЈ-H and 2ЈЈЈ-H with 6-H, 7-H and 8-H and by a long-range C-H correlation from 1ЈЈЈ-H to C-7.…”

Section: Resultssupporting

confidence: 54%

“…As close mimics of biologically relevant systems, and also for consistency with a previous analysis of archazolid A, [10] these compounds were studied in CD 3 OD, in which optimum 1 H NMR signal dispersion was achieved at the highest available field strength (600 MHz). A combination of multiplet analysis, [13] homonuclear decoupling and TOCSY experiments at different mixing times ( Figure 2) were used for determination of all 3 J H,H coupling constants, and information on the spatial relationships between nonadjacent protons was deduced from ROESY experiments. Within the macrocyclic core, all analogues show a characteristic sequence of large (Ͼ8 Hz) and small (Ͻ4 Hz) 3 J H,H coupling constants, together with a series of highly specific transannular NOE correlations, which indicate a high degree of structural rigidity for the macrocycle.…”

Section: Resultsmentioning

confidence: 99%

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Archazolid‐7‐O‐β‐D‐glucopyranoside – Isolation, Structural Elucidation and Solution Conformation of a Novel V‐ATPase Inhibitor from the Myxobacterium Cystobacter violaceus

Menche¹,

Hassfeld²,

Steinmetz³

et al. 2007

Eur J Org Chem

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The novel polyketide macrolide archazolid-7-O-β-D-glucopyranoside (3) has been isolated from the myxobacterium Cystobacter violaceus and the structure of this first archazolidglycoside has been determined by spectroscopic and degradative methods. A synthesis of simplified 7-O analogues, based on regioselective derivatisation of archazolid A, was elaborated. These structurally novel archazolids of natural

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Section: Resultssupporting

confidence: 54%

Section: Resultsmentioning

confidence: 99%

Archazolid‐7‐O‐β‐D‐glucopyranoside – Isolation, Structural Elucidation and Solution Conformation of a Novel V‐ATPase Inhibitor from the Myxobacterium Cystobacter violaceus

Menche¹,

Hassfeld²,

Steinmetz³

et al. 2007

Eur J Org Chem

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“…30 For the products with nonsymmetrical molecules, most coupling constants in 1 H NMR could be measured directly from the corresponding multiplets assuming the first order of spectra (for methodology see ref. 31). The large vicinal coupling constants between the cyclohexane protons H3a and H7a geminal to the sulphur atoms (12.1-12.4 Hz) proved unambiguously the trans-diaxial position of these protons and, correspondingly, the trans-diequatorial position of the sulphur atoms in the cyclohexane derivatives 2c -2i (Figure 1).…”

Section: Stereochemistry Of Productsmentioning

confidence: 83%

Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks

Dotsenko¹,

Zhao²,

Franz³

et al. 2014

Arkivoc

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A series of novel 1,3-dithiolane-2-thiones, or cyclic trithiocarbonates, has been prepared by a new simple procedure: a treatment of the corresponding epoxides with the commercially available potassium ethyl xanthogenate, KSC(S)OEt. The stereochemistry of the products was determined by 1 H NMR and in some cases by single-crystal X-ray data. Cyclohexane-based 1,3-dithiolane-2-thiones revealed a trans-fusion of the carbo-and hetero-cycles. The products obtained from the mono-substituted cyclohexene oxides demonstrated an axial position of the substituents. Thus the epoxide transformation into trithiocarbonate can be used as a method for locking cyclic compounds in unstable conformations.

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“…Given NJ, the overall number of coupling constants giving rise to a multiplet, the general protocol of generating an inverted splitting tree is as follows: 15 1. The smallest coupling constant J1 is identified.…”

Section: Resultsmentioning

confidence: 99%

A new approach to automated first‐order multiplet analysis

Golotvin¹,

Vodopianov²,

Williams³

2002

Magnetic Reson in Chemistry

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The dependence of the values of NMR spin-spin coupling constants on molecular conformation can be a valuable tool in the structure determination process. The continuing increase in the resonance frequency of modern NMR spectrometers allows an increasing number of resonances to be examined using first-order multiplet analysis. While this can easily be done for the simplest patterns (doublets, triplets, quartets), more complex patterns can be extremely difficult to analyze. The task of deducing the coupling constant values from a multiplet is the reverse process of generating a conventional splitting tree from a single line (chemical shift) by sequential branching using a given set of coupling constants. We present a simple, straightforward method of deducing coupling constant values from first-order multiplets based on a general inverted splitting tree algorithm but also including a peak intensity normalization procedure that utilizes multiplet symmetry and generates a set of possible first-order intensity distribution patterns. When combined with an inverted splitting tree algorithm, it is possible to find an intensity pattern that allows the deduction of a proper set of coupling constants.

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A Practical Guide to First-Order Multiplet Analysis in 1H NMR Spectroscopy

Cited by 65 publications

References 0 publications

Archazolid‐7‐O‐β‐D‐glucopyranoside – Isolation, Structural Elucidation and Solution Conformation of a Novel V‐ATPase Inhibitor from the Myxobacterium Cystobacter violaceus

Archazolid‐7‐O‐β‐D‐glucopyranoside – Isolation, Structural Elucidation and Solution Conformation of a Novel V‐ATPase Inhibitor from the Myxobacterium Cystobacter violaceus

Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks

A new approach to automated first‐order multiplet analysis

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