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Influence of Alcohol [beta]-Fluorination on Hydrogen-Bond Acidity of Conformationally Flexible Substrates

Graton, Jerome ; Compain, Guillaume ; Besseau, Francois ; Bogdan, Elena ; Watts, Joseph M ; Mtashobya, Lewis ; Wang, Zhong ; Weymouth-Wilson, Alex ; Galland, Nicolas ; LeQuestel, Jean-Yves ; Linclau, Bruno

Chemistry : a European journal, 2017-02, Vol.23 (12), p.2811 [Periódico revisado por pares]

Weinheim: Wiley Subscription Services, Inc

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  • Título:
    Influence of Alcohol [beta]-Fluorination on Hydrogen-Bond Acidity of Conformationally Flexible Substrates
  • Autor: Graton, Jerome ; Compain, Guillaume ; Besseau, Francois ; Bogdan, Elena ; Watts, Joseph M ; Mtashobya, Lewis ; Wang, Zhong ; Weymouth-Wilson, Alex ; Galland, Nicolas ; LeQuestel, Jean-Yves ; Linclau, Bruno
  • Assuntos: Alcohol
  • É parte de: Chemistry : a European journal, 2017-02, Vol.23 (12), p.2811
  • Descrição: 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 OHF 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 [beta]-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 OHF IMHB, as well as by the strength of these IMHBs. We also show that the Kenny theoretical V[alpha](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 OHF IMHB in the modulation of alcohol H-bond donating capacity.
  • Editor: Weinheim: Wiley Subscription Services, Inc
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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