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Conformational studies on pertrimethylsilyl derivatives of some mono- and disaccharides by 220 MHz PMR spectroscopy

Dirk G. Streefkerk, +2 more
- 01 Jan 1973 - 
- Vol. 29, Iss: 6, pp 833-844
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TLDR
In this article, a complete interpretation of 220 MHz PMR spectra and the accurate chemical shifts and coupling constants, obtained after computer simulation of the spectra, of a number of TMS-mono and disaccharides are given.
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This article is published in Tetrahedron.The article was published on 1973-01-01 and is currently open access. It has received 70 citations till now. The article focuses on the topics: Karplus equation & Cyclohexane conformation.

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Citations
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Prediction of anti and gauche vicinal proton‐proton coupling constants in carbohydrates: A simple additivity rule for pyranose rings

TL;DR: In this article, a set of parameters were used to calculate 3J(HH) coupling constants in a variety of pyranosides and related compounds and a comparison with experimental values taken from the literature showed that couplings in molecules which are conformationally pure and underformed can be predicted with a surprising accuracy.
Journal ArticleDOI

Characterization of neutral sugars and uronic acids after methanolysis and trimethylsilylation for recognition of plant gums

TL;DR: The main neutral sugars and uronic acids that occur as components of plant gums were methanolysed and silylated for study by gas chromatography, and the results of the above identification were applied to the analysis of some gums and a seventeenth century ink sample as mentioned in this paper.
References
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Journal ArticleDOI

Contact Electron‐Spin Coupling of Nuclear Magnetic Moments

TL;DR: In this article, the valence-bond theory for the contact electron-spin coupling of nuclear magnetic moments is used to calculate the proton−proton, proton-fluorine, and fluorine-florine coupling constants in ethanic and ethylenic molecules.
Journal ArticleDOI

Nuclear Spin Coupling Between Geminal Hydrogen Atoms

TL;DR: In this paper, a molecular orbital theory of nuclear spin coupling between geminal hydrogen atoms is developed and found to give a satisfactory interpretation of substituent effects evident in experimental data, suggesting that the value of geminal coupling constants provides a means of distinguishing between inductive and hyperconjugative electron transfer.
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Q1. What contributions have the authors mentioned in the paper "Conformational studies on pertrimethyl- silyl derivatives of some mono- and disaccharides by 220 mhz pmr spectroscopy" ?

By means of an adapted Karplus equation the conformation of the derivatives has been studied in detail. 

By studying the conformational changes due to different substituents in a series of closely related compounds, most of the uncertainties in the constants in the Karplus equation and in the other factors (e.g. bond lengths, bond angles), influencing the vicinal coupling constants, are largely eliminated. 

As a consequence of the strong deshiekling effect of the ring oxygen, the doublets of the anomeric protons (H-l) are found between 6 = 4-3 and 5-7 ppm. 

An indication, that the parallel 1,3-interaction is a very important factor in disfavouring a rotamer, is given by the negligible amounts of rotamer 3 in the o-galactopyranose units of 5, 6, 9 and IO (n3 - 0, columns a and b). 

For the compound l-thiopentakis-OAc-/3-D-galactopyranose the following mole fractions were found n, = O-09, nz = 0.91 and rz3 = 003, in which n, and n2 can be interchanged. 

Although the axial group at C-l has only the ring oxygen at the adjacent place, it is still likely that the overall effect is a less pronounced flattening of this ring fragment (Fig 5) and a decreasing of 4. 

J”H’= (7~8-l~cos#~+5~6cos2~)(1-O~lAX) (2)*A value of 3.5 for )(oTLbs was used; tbis value was calculated by the method of Cavanaugb and Dailey” from PMR data of CHs-CHI-OSi(CH$s.16 

In the glucopyranose unit the protons H-3, H-4, H-5 and H-6 give rise to a complex multiple& which could not be analyzed further. 

This result reinforces the conclusions about the TMS-D-galactopyranoses, because it is likely to assume that the TMS- andAC-derivatives of D-galactopymnose do not differ greatly with respect to the conformational preferences of the C-5-C-6 fragment. 

An elecpresent when 0 = 0” (Fig 3b); if 0 = 60” the effect is tronegative group R has its maximum effect when R nearly absenP (Fig 3~).