Francois Besseau
Current Organizations / Institutes
The organizations/institutes from the scholar's latest article
Research Subjects
Research Interests
Francois Besseau has a total of 10 co-authors. Here are the top co-authors by number of shared publications:
- Alex Weymouth-Wilson
ICE Pharma, 68 Weld Street, RD2, Palmerston North 4472, New Zealand
1 shared publication - Bruno Linclau
Department of Organic and Macromolecular Chemistry Campus Sterre Ghent University Ghent Belgium
1 shared publication - Elena Bogdan
CEISAM UMR CNRS 6230, Faculté des Sciences et des Techniques, Université de Nantes, 2, rue de la Houssinière, BP 92208, 44322, Nantes Cedex 3, France
1 shared publication - Guillaume Compain
Univ. Bordeaux, CNRS, Bordeaux INP, CBMN, UMR 5248, IECB 33600 Pessac France
1 shared publication - Jean-Yves Le Questel
CEISAM UMR CNRS 6230 CNRS Nantes Université Nantes France
1 shared publication - Joseph M. Watts
Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK
1 shared publication
Latest Publications
- 27 December 2016
- Published by Wiley in Chemistry – A European Journal
- Vol. 23 (12) , 2811-2819
Influence of Alcohol β‐Fluorination on Hydrogen‐Bond Acidity of Conformationally Flexible Substrates
Rational modulations of molecular interactions are of significant importance in compound properties optimization. We have previously shown that fluorination of conformationally rigid cyclohexanols leads to attenuation of their hydrogen‐bond (H‐bond) donating capacity (designated by pKAHY) when OH⋅⋅⋅F intramolecular hydrogen‐bond (IMHB) interactions occur, as opposed to an increase in pKAHY due to the fluorine electronegativity. This work has now been extended to a wider range of aliphatic β‐fluorohydrins with increasing degrees of conformational flexibility. We show that the observed differences in pKAHY between closely related diastereomers can be fully rationalized by subtle variations in populations of conformers able to engage in OH⋅⋅⋅F IMHB, as well as by the strength of these IMHBs. We also show that the Kenny theoretical Vα(r) descriptor of H‐bond acidity accurately reflects the observed variations and a calibration equation extended to fluorohydrins is proposed. This work clearly underlines the importance of the weak OH⋅⋅⋅F IMHB in the modulation of alcohol H‐bond donating capacity.
- 27 December 2016
- Published by Wiley in Chemistry – A European Journal
- Vol. 23 (12) , 2811-2819
Influence of Alcohol β‐Fluorination on Hydrogen‐Bond Acidity of Conformationally Flexible Substrates
Rational modulations of molecular interactions are of significant importance in compound properties optimization. We have previously shown that fluorination of conformationally rigid cyclohexanols leads to attenuation of their hydrogen‐bond (H‐bond) donating capacity (designated by pKAHY) when OH⋅⋅⋅F intramolecular hydrogen‐bond (IMHB) interactions occur, as opposed to an increase in pKAHY due to the fluorine electronegativity. This work has now been extended to a wider range of aliphatic β‐fluorohydrins with increasing degrees of conformational flexibility. We show that the observed differences in pKAHY between closely related diastereomers can be fully rationalized by subtle variations in populations of conformers able to engage in OH⋅⋅⋅F IMHB, as well as by the strength of these IMHBs. We also show that the Kenny theoretical Vα(r) descriptor of H‐bond acidity accurately reflects the observed variations and a calibration equation extended to fluorohydrins is proposed. This work clearly underlines the importance of the weak OH⋅⋅⋅F IMHB in the modulation of alcohol H‐bond donating capacity.