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SINAPSE experts from around Scotland have developed ten online modules designed to explain medical imaging. They are freely available and are intended for non-specialists.


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Online Short Courses

The C-F bond as a tool in the conformational control of amides

Author(s): C. R. S. Briggs, D. O'Hagan, J. A. K. Howard, D. S. Yufit

Abstract:
The conformation of 2-fluoro-N-(2-fluoroethyl)-propionamide 4 in the solid state indicates the influence of both a P-fluorine-amide gauche effect and an alpha-fluoroamide effect. The structure reveals the influence of two recently observed stereoelectronic effects associated with the C-F bond, which has resulted in the successful prediction of the solid state conformation of amide 4. A gauche relationship (-69.9degrees) was observed for atoms N(1)-C(4)-C(5)-F and a syn planar (2.0degrees) relationship was observed for N(1)-C(3)-C(2)-F. The paper demonstrates the predictive power of using the C-F bond as a tool in influencing the conformation of amides and peptides. (C) 2002 Elsevier Science B.V. All rights reserved.

Full version: Available here

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ISBN: 0022-1139
Publication Year: 2003
Periodical: Journal of Fluorine Chemistry
Periodical Number: 1
Volume: 119
Pages: 9-13
Author Address: