ArticleBeilstein journal of organic chemistry2014
The difluoromethylene (CF2) group in aliphatic chains: Synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups.
Article in Beilstein journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed, 46 citations in OpenAlex.
- Origami with small molecules: exploiting the C-F bond as a conformational tool.Beilstein journal of organic chemistry · 2025Review
- Conformational Analysis of 1,3-Difluorinated Alkanes.The Journal of organic chemistry · 2024Article
- Enyne difluorination.Nature chemistry · 2023Article
- Regioselective, catalytic 1,1-difluorination of enynes.Nature chemistry · 2023Article
- Programmable synthesis of difluorinated hydrocarbons from alkenes through a photocatalytic linchpin strategy.Chemical science · 2023Article
- Catalytic Hydrodifluoroalkylation of Unactivated Olefins.Organic letters · 2022Article
- (Fluoro)alkylation of alkenes promoted by photolysis of alkylzirconocenes.Chemical science · 2022Article
- Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties.Molecules (Basel, Switzerland) · 2021Article
- Synthesis of a Hominal Bis(difluoromethyl) Fragment.ACS omega · 2019Article
- Visible light-mediated difluoroalkylation of electron-deficient alkenes.Beilstein journal of organic chemistry · 2018Article
- 5-Fluoroimidazo[4,5-b]pyridine Is a Privileged Fragment That Conveys Bioavailability to Potent Trypanosomal Methionyl-tRNA Synthetase Inhibitors.ACS infectious diseases · 2016Article
- Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring.Beilstein journal of organic chemistry · 2016Article
- Influence of Fluorination on the Conformational Properties and Hydrogen-Bond Acidity of Benzyl Alcohol Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes.Beilstein journal of organic chemistry · 2015Article
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4 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
The syntheses of palmitic acids and a nonadecane are reported with CF2 groups located 1,3 or 1,4 to each other along the aliphatic chain. Specifically 8,8,10,10- and 8,8,11,11-tetrafluorohexadecanoic acids (6b and 6c) are prepared as well as the singly modified analogue 8,8-difluorohexadecanoic acid (6a). Also 8,8,11,11-tetrafluorononadecane (27) is prepared as a pure hydrocarbon containing a 1,4-di-CF2 motif. The modified palmitic acids are characterized by differential scanning calorimetry (DSC) to determine melting points and phase behaviour relative to palmitic acid (62.5 °C). It emerges that 6c, with the CF2 groups placed 1,4- to each other, has a significantly higher melting point (89.9 °C) when compared to the other analogues and palmitic acid itself. It is a crystalline compound and the structure reveals an extended anti-zig-zag chain. Similarly 8,8,11,11-tetrafluorononadecane (27) adopts an extended anti-zig-zag structure. This is rationalized by dipolar relaxation between the two CF2 groups placed 1,4 to each other in the extended anti-zig-zag chain and suggests a design modification for long chain aliphatics which can introduce conformational stability.
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