Conformational analysis and intramolecular interactions in monosubstituted phenylboranes and phenylboronic acids

• Josué M. Silla,
• Rodrigo A. Cormanich,
• Roberto Rittner and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2013, 9, 1127–1134, doi:10.3762/bjoc.9.125

• for 2-monohalogen substituted phenols [12]. In fact, organic fluorine has been found to hardly ever participate in hydrogen bonding [13], despite the appearance of this interaction in 8-fluoro-4-methyl-1-naphthol [14], 2'-fluoroflavonols [15], 2-fluorobicyclo[2.2.1]heptan-7-ols [16] and 2

Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols

• Fátima M. P. de Rezende,
• Marilua A. Moreira,
• Rodrigo A. Cormanich and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2012, 8, 1227–1232, doi:10.3762/bjoc.8.137

• .8.137 Abstract Four diastereoisomers of 2-fluorobicyclo[2.2.1]heptan-7-ols were computationally investigated by using quantum-chemical calculations, and their relative energies were analyzed on the basis of stereoelectronic interactions, particularly the presence or otherwise of the F∙∙∙HO

• bond. Keywords: conformational analysis; 2-fluorobicyclo[2.2.1]heptan-7-ols; hydrogen bond; 1hJF,H(O) coupling constant; quantum-chemical calculations; Introduction Intra- and intermolecular hydrogen bonds (HB) play an important role in determining the molecular arrangements and properties, as well

• steric effect, but it suppresses adventitious metabolism, influences the pKa of functional groups, and alters solution conformation [12]. In this context, conformational screening and theoretical evaluation of 2-fluorobicyclo[2.2.1]heptan-7-ols (2-fluoronorbornan-7-ols, compounds 5–8 in Figure 1