The Reverse Fluorine Perlin-like Effect and Related Stereoelectronic Interactions

Author(s)

Silla, Josue M. ^[1] ; Freitas, Matheus P. ^[1] ; Cormanich, Rodrigo A. ^[2] ; Rittner, Roberto ^[2]

Affiliation

^[1] Univ Fed Lavras, Dept Chem, BR-37200000 Lavras, MG - Brazil

^[2] Univ Estadual Campinas, Inst Chem, BR-13084971 Campinas, SP - Brazil

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 79, n. 13, p. 6385-6388, JUL 4 2014.
• Web of Science Citations: 13

Abstract

A similar effect to the well-known reverse Perlin effect was observed on the (1)J(C-F) coupling constants of alpha- and beta-D-glucopyranosyl fluoride tetracetate, both in nonpolar and polar solution. This can be called ``reverse fluorine Perlin-like effect{''}, and it is shown to be ruled by dipolar interactions rather than by hyperconjugation. The reverse fluorine Perlin-like effect does not have a general relationship with the anomeric effect, and it can be useful to determine the structure and stereochemistry of organofluorine compounds. (AU)

• FAPESP's process: 12/03933-5 - Conformational equilibria and intramolecular interactions for a series of amino-acids: theoretical and experimental approaches
• Grantee: Roberto Rittner Neto
• Support type: Regular Research Grants
• FAPESP's process: 11/01170-1 - Physicochemical studies of organic compounds: long range inractions and conformational analysis of organofluorine compounds.
• Grantee: Rodrigo Antonio Cormanich
• Support type: Scholarships in Brazil - Doctorate