期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 15, 页码 7764-7769出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01072
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资金
- Research Corporation for Scientific Advancement
- Thomas Lord Charitable Trust Fellowship
- Allegheny College
- NSF [0087210, 1337296]
- Ohio Board of Regents [CAP-491]
- Youngstown State University
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1337296] Funding Source: National Science Foundation
Although fluorine often plays an influential role in molecular recognition, little is known about the effect of aliphatic fluorine on the CH-pi interaction in solution. A series of molecular balances were synthesized that contain fluorinated and nonfluorinated alkyl groups. Our findings indicate that fluorine's polarizing ability does enhance CH-7r binding and depends on molecular orientation. Surprisingly, when the terminal end of the alkyl group is completely fluorinated, the balance tips toward fluorophobicity and assumes an unusual constrained conformation.
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