Synthesis of ω-Hydroxy Quaternary Ammonium Bolaform Surfactants

1998 ◽  
Vol 51 (7) ◽  
pp. 581 ◽  
Author(s):  
Tim W. Davey ◽  
Alan R. Hayman
Keyword(s):  
Biological Activity ◽  
Antifungal Activity ◽  
Chain Length ◽  
Quaternary Ammonium ◽  
Hydrocarbon Chain ◽  
Biological Properties ◽  
Ammonium Bromide ◽  
Hydrocarbon Chain Length ◽  
Antimicrobial And Antifungal Activity

Several members of a novel class of w-substituted asymmetric bolaform surfactants have been synthesized in order to investigate their surfactant and biological properties. The ω-hydroxy trialkylammonium and pyridinium surfactants have significant antimicrobial and antifungal activity relative to their conventional analogues. For conventional quaternary ammonium alkyl surfactants, increasing the hydrocarbon chain length causes a decrease in the surfactant monomer solubility and a corresponding decrease in the biological activity. No such trend is observed for the ω-hydroxy quaternary ammonium bromide series.

scholarly journals Structure and Interdigitation of Chain-Asymmetric Phosphatidylcholines and Milk Sphingomyelin in the Fluid Phase

Symmetry ◽  
2021 ◽  
Vol 13 (8) ◽  
pp. 1441
Author(s):  
Moritz P. K. Frewein ◽  
Milka Doktorova ◽  
Frederick A. Heberle ◽  
Haden L. Scott ◽  
Enrico F. Semeraro ◽  
...  
Keyword(s):  
Chain Length ◽  
Hydration Shell ◽  
Fluid Phase ◽  
Hydrocarbon Chain ◽  
Specific Model ◽  
Glycerol Backbone ◽  
Membrane Composition ◽  
Membrane Structures ◽  
Hydrocarbon Chain Length ◽  
Dynamics Simulations

We addressed the frequent occurrence of mixed-chain lipids in biological membranes and their impact on membrane structure by studying several chain-asymmetric phosphatidylcholines and the highly asymmetric milk sphingomyelin. Specifically, we report trans-membrane structures of the corresponding fluid lamellar phases using small-angle X-ray and neutron scattering, which were jointly analyzed in terms of a membrane composition-specific model, including a headgroup hydration shell. Focusing on terminal methyl groups at the bilayer center, we found a linear relation between hydrocarbon chain length mismatch and the methyl-overlap for phosphatidylcholines, and a non-negligible impact of the glycerol backbone-tilting, letting the sn1-chain penetrate deeper into the opposing leaflet by half a CH2 group. That is, penetration-depth differences due to the ester-linked hydrocarbons at the glycerol backbone, previously reported for gel phase structures, also extend to the more relevant physiological fluid phase, but are significantly reduced. Moreover, milk sphingomyelin was found to follow the same linear relationship suggesting a similar tilt of the sphingosine backbone. Complementarily performed molecular dynamics simulations revealed that there is always a part of the lipid tails bending back, even if there is a high interdigitation with the opposing chains. The extent of this back-bending was similar to that in chain symmetric bilayers. For both cases of adaptation to chain length mismatch, chain-asymmetry has a large impact on hydrocarbon chain ordering, inducing disorder in the longer of the two hydrocarbons.

scholarly journals Effect of Hydrocarbon Chain Length of Amphiphilic Ruthenium Dyes on Solid-State Dye-Sensitized Photovoltaics

Nano Letters ◽  
2005 ◽  
Vol 5 (7) ◽  
pp. 1315-1320 ◽  
Author(s):  
Lukas Schmidt-Mende ◽  
Jessica E. Kroeze ◽  
James R. Durrant ◽  
Md. K. Nazeeruddin ◽  
Michael Grätzel
Keyword(s):  
Solid State ◽  
Chain Length ◽  
Hydrocarbon Chain ◽  
Dye Sensitized ◽  
Hydrocarbon Chain Length ◽  
Ruthenium Dyes

Cation exchange in synthetic manganates: II. The structure of an alkylammonium-saturated phyllomanganate

Clay Minerals ◽  
1986 ◽  
Vol 21 (5) ◽  
pp. 957-964 ◽  
Author(s):  
E. Paterson ◽  
D.R. Clark ◽  
D. Russell ◽  
R. Swaffield
Keyword(s):  
Chain Length ◽  
Photoelectron Spectroscopy ◽  
Hydrocarbon Chain ◽  
Exchange Capacity ◽  
Basal Spacing ◽  
Water Molecules ◽  
Interlayer Water ◽  
X Ray ◽  
Alkyl Chains ◽  
Hydrocarbon Chain Length

AbstractA synthetic phyllomanganate saturated with a series of primary alkylammonium cations has been examined using XRD, chemical analysis and X-ray photoelectron spectroscopy. A linear relationship exists between the basal spacing of the saturated alkylammonium-manganate and the hydrocarbon chain length in the interlayer, and from the gradient it is concluded that the alkyl chains are perpendicular to the manganate sheet. This orientation is a function of both the charge density and the presence of a layer of water molecules immediately adjacent to the manganate basal surfaces. Evacuation results in the loss of this interlayer water and the structure of the organo-manganate is considerably disrupted. The extent to which the interlayer arrangement can be reinstated by rehydration is dependent on the chain length of the saturating organo-cation. For cations of chain length > C6 the C contents suggest that cation in excess of the exchange capacity is present in the interlayer, but the absence of any compensating anion and the release of amine on evacuation suggests that the excess C arises from the presence of free amine.

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