TY - JOUR
T1 - Organic fluorine as a hydrogen-bond acceptor
T2 - Recent examples and applications
AU - Champagne, Pier Alexandre
AU - Desroches, Justine
AU - Paquin, Jean François
N1 - Funding Information:
This work was supported by the Canada Research Chair Program, the Natural Sciences and Engineering Research Council of Canada and the Université Laval.
Publisher Copyright:
© 2015, Georg Thieme Verlag Stuttgart New York.
PY - 2015/2/1
Y1 - 2015/2/1
N2 - For more than three decades, the ability of a fluorine atom involved in a C-F bond to act as a hydrogen-bond acceptor has been a controversial issue. Throughout the years, more and more evidence has been published to support this hypothesis and it is now difficult to doubt the existence of the hydrogen bond with organic fluorine. However, since this interaction has low binding energies, it is sometimes difficult to clearly demonstrate its presence or effect in a system. In the present review, only the most recent examples from the literature are presented and the different techniques used to prove the presence of these C-F·H-X hydrogen bonds are compared and discussed according to the accepted criteria for hydrogen bonding detailed by a recent IUPAC committee. Even with its weak interaction energy, hydrogen bonds to organic fluorine have the potential to affect properties of practical systems in different spheres of chemistry. All the recent examples of such effects are highlighted.
AB - For more than three decades, the ability of a fluorine atom involved in a C-F bond to act as a hydrogen-bond acceptor has been a controversial issue. Throughout the years, more and more evidence has been published to support this hypothesis and it is now difficult to doubt the existence of the hydrogen bond with organic fluorine. However, since this interaction has low binding energies, it is sometimes difficult to clearly demonstrate its presence or effect in a system. In the present review, only the most recent examples from the literature are presented and the different techniques used to prove the presence of these C-F·H-X hydrogen bonds are compared and discussed according to the accepted criteria for hydrogen bonding detailed by a recent IUPAC committee. Even with its weak interaction energy, hydrogen bonds to organic fluorine have the potential to affect properties of practical systems in different spheres of chemistry. All the recent examples of such effects are highlighted.
KW - Computational analysis
KW - Organofluorine chemistry
KW - Spectroscopic measurements
KW - Weak hydrogen bonds
KW - X-ray crystallography
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U2 - 10.1055/s-0034-1379537
DO - 10.1055/s-0034-1379537
M3 - Review article
AN - SCOPUS:84922285661
SN - 0039-7881
VL - 47
SP - 306
EP - 322
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 3
ER -