Significant inter- and intramolecular O-H•••FC hydrogen bonding

Significant inter- and intramolecular O-H•••FC hydrogen bonding
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DOI:
10.1021/ja983552e
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发表时间:
1999-05-05
影响因子:
15
通讯作者:
Strauss, SH
Strauss, SH
中科院分区:
化学1区
文献类型:
--
作者:
Barbarich, TJ;Rithner, CD;Strauss, SH

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The incorporation of one or more fluorine atoms into biologically active compounds continues to be an active endeavor. 1 Many bioorganic chemists and biochemists believe that the formation of intermolecular OH ‚‚‚FC and NH ‚‚‚FC hydrogen bonds may be important in the binding of fluorinated substrates to enzyme active sites. 2 Nevertheless, the role of organic fluorine atoms as hydrogen bond acceptors in at least some systems remains controversial, 3, 4 in part because there are few detailed studies of “unconstrained” intermolecular OH ‚‚‚FC and NH ‚‚‚FC hydrogen bonds that are formed in the absence of other, stronger intermolecular interactions. We now report the synthesis and characterization of the first member of a new class of fluorinated alcohols, a class that may allow inter-and intramolecular OH ‚‚‚FC hydrogen bonding to be systematically studied in great detail.