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Why do so few simple acyclic acetals adopt the classic anomeric conformation? The eclipsed anomeric conformation for acetals. An analysis of crystal structures, molecular mechanics calculations, and NMR measurements

Anderson, JE; (2000) Why do so few simple acyclic acetals adopt the classic anomeric conformation? The eclipsed anomeric conformation for acetals. An analysis of crystal structures, molecular mechanics calculations, and NMR measurements. Journal of Organic Chemistry , 65 (3) pp. 748-754. 10.1021/jo991553z.

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Abstract

A novel conformation for simple acyclic acetals, the eclipsed anomeric conformation is recognized and shown to be somewhat more common than the classic anomeric conformation, by an analysis of structures in the Cambridge Crystallographic Database and of molecular mechanics calculations, and by NMR measurements of simple model acetals. The classic and eclipsed anomeric conformations differ principally by rotation through 180°about one central carbon-oxygen bond. Both conformations involve anomeric interactions, but the eclipsed conformation better accommodates steric interactions of groups linked by relatively short carbon-oxygen bonds.

Type: Article
Title: Why do so few simple acyclic acetals adopt the classic anomeric conformation? The eclipsed anomeric conformation for acetals. An analysis of crystal structures, molecular mechanics calculations, and NMR measurements
DOI: 10.1021/jo991553z
UCL classification: UCL > School of BEAMS > Faculty of Maths and Physical Sciences
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/23858
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