The specification of asymmetric configuration in organic chemistry

Cahn, R. S.; Ingold, C. K.; Prelog, V.

doi:10.1007/bf02157171

Cited by 796 publications

(181 citation statements)

References 13 publications

Supporting

Mentioning

166

Contrasting

Unclassified

Order By: Relevance

“…The application of Hamilton's generalized R factor method (Hamilton, 1965) to test the validity of the configurational assignments shows that the probability of the S configuration being the correct one is considerably smaller than 0.001%, so that the configuration around the sulfur atom is R in the notation of Cahn, Ingold & Prelog (1956). This is in agreement with the absolute configuration assigned by Axelrod et al (1968).…”

Section: Discussionmentioning

confidence: 83%

The crystal structure and absolute configuration of (+)-methyl-p-tolyl sulfoxide

Camp¹,

Hope²

1970

Acta Crystallogr Sect B

View full text Add to dashboard Cite

The crystal structure of (+)-methyl p-tolyl sulfoxide has been solved by the heavy-atom method and refined by Fourier and least-squares techniques. The absolute configuration has been determined by the anomalous phase displacement technique with the sulfur atom acting as the anomalous scatterer. The space group is P212121 with four molecules per unit cell of dimensions a = 5-826 (6), b = 8.621 (8) and c= 16"435 (3) A. Three-dimensional data (Cu Ke) were dollected with a Picker automatic diffractometer. The final R indices obtained for the two configurations are 0.034 and 0.044 respectively, for 832 observed reflections. In the notation of Cahn, Ingold & Prelog the correct absolute configuration at sulfur is R; the same assignment had been made earlier on the basis of chemical evidence.

show abstract

Section: Discussionmentioning

confidence: 83%

The crystal structure and absolute configuration of (+)-methyl-p-tolyl sulfoxide

Camp¹,

Hope²

1970

Acta Crystallogr Sect B

View full text Add to dashboard Cite

show abstract

“…tion at carbon I-C2 and /^-configuration at carbon II-C2, according to the nomenclature of CahnIngold-Prelog [6].…”

Section: Resultsmentioning

confidence: 99%

Stereochemistry of Two Hydroxybiflavanonols from Garcinia cola Nuts

Sonnenbichler

Madubunyi

Scheer³

1987

Zeitschrift Für Naturforschung C

View full text Add to dashboard Cite

show abstract

“…Allen, Rowland, Fortier & Glasgow, 1990). In particular, we wish to answer three questions: (i) can we classify the hexopyranose structures using only the information available in the CSD [this information does not, at present, include codified stereochemical descriptors, for example the R,S descriptions of Cahn, Ingold & Prelog (1956)], (ii) can we gain insight from the classification, and (iii) can we predict any missing classes. In assessing the success of any automated methodology, we must begin by using well known examples.…”

Section: Introductionmentioning

confidence: 99%

Stereochemical and conformational classification of the hexopyranose sugars using numerical clustering methods

Allen¹,

Fortier²

1993

Acta Crystallogr Sect B

View full text Add to dashboard Cite

The methods of single-linkage and complete-linkage cluster analysis have been used to generate, in a rapid and semi-automatic manner, a variety of configurational and conformational classifications of 249 hexopyranose fragments retrieved from the Cambridge Structural Database. Conformational aspects of the fragment were described using standard torsion angles, while configurations adopted at the ring carbons were described by five projected valence angles. The classification experiments show that (a) the pyran ring adopts a 4C~-chair conformation in all but ten of the fragments, where it is found that the conformation adopted is that of a ~C4 chair, (b) only 14 (of a possible 32) hexopyranose stereoisomers are represented in the crystallographic data, and (c) the C6--O6 side chain adopts only + gauche, -gauche and trans conformations. Clustering methods were also used to obtain representative orthogonal coordinates that permit the building of approximate models of hexopyranose units for which crystal structures are not yet available. The analyses indicate that the ten crystal structures having a m C4 pyran-ring conformation may be reporting coordinates which describe the wrong enantiomorph. This automated data analysis indicates desirable extensions of the cluster-analysis methodology and also suggests improvements to the evaluation, search and display facilities of the Cambridge Structural Database System.

show abstract

The specification of asymmetric configuration in organic chemistry

Cited by 796 publications

References 13 publications

The crystal structure and absolute configuration of (+)-methyl-p-tolyl sulfoxide

The crystal structure and absolute configuration of (+)-methyl-p-tolyl sulfoxide

Stereochemistry of Two Hydroxybiflavanonols from Garcinia cola Nuts

Stereochemical and conformational classification of the hexopyranose sugars using numerical clustering methods

Contact Info

Product

Resources

About