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gauche effect

  1. The stabilization of the gauche (synclinal) conformation in a two carbon unit bonded vicinally to electronegative elements e.g. 1,2-difluoroethane.
  2. The destabilization of the gauche (synclinal) conformation in a two carbon unit bonded vicinally to large, soft and polarizable elements such as sulfur and bromine.
Source:
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2209
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A.Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. https://doi.org/10.1351/goldbook.
DOI of this term: https://doi.org/10.1351/goldbook.G02595
Original PDF version (may be out of date): http://www.iupac.org/goldbook/G02595.pdf.
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