First Example of Surfactants Enclosing a Semipolar Nitrogen−Boron Bond

and, Jean-Brice Le Toumelin; Baboulène, M.

doi:10.1021/la951030w

Cited by 10 publications

(3 citation statements)

References 16 publications

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“…This provides further reaction-based evidence that the BN bond in aminoboranes contains substantial double-bond character . While to our knowledge no multistep syntheses have employed this hetero-ene rearrangement yet, applications of amine-boranes and aminoboranes containing alkenyl substituents have been reported 1 …”

Section: Introductionmentioning

confidence: 64%

Pericyclic Reactions between Aminoboranes R₂BNR₂‘ and Alkenes: [4+2] vs [2+2] Transition States

Bissett

Gilbert

2004

Organometallics

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Computational comparison of the [2+2] and [4+2] reactions between aminoboranes R2BNR‘2 and alkenes CH2CH(R‘ ‘) shows that the latter are strongly preferred. The preference arises from the [4+2] reactions exhibiting lower reaction barriers than do the [2+2] reactions; the products formed are of nearly equal stability. This behavior mimics that of reactions between alkenes and supports viewing aminoboranes, particularly (F3C)2BNMe2, as acting like polar alkenes.

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Section: Introductionmentioning

confidence: 64%

Pericyclic Reactions between Aminoboranes R₂BNR₂‘ and Alkenes: [4+2] vs [2+2] Transition States

Bissett

Gilbert

2004

Organometallics

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“…They have also examined the interaction of these polymers with semiconducting single-walled carbon nanotubes (SWNTs) using different spectroscopies, and finally examined the ability of these polymer-SWNTs to modulate fluorescence emission in response to different saccharides. Baboulene et al synthesized some amino organo boron amphiphilic molecules that have been shown to have interesting surfactant properties. In recent reports, it was established that long chain amino-boronic acid and its salt shows amphiphilic character in aqueous solution with excellent surface-active properties. , Karpichev and co-workers very recently reported a new approach for creating water-soluble functionalized vesicles employing N -alkyl-3-boronopyridinium triflates (alkyl = CH 3 , C 12 H 25 , C 16 H 33 ) as sensors for monosaccharides .…”

Section: Introductionmentioning

confidence: 99%

Effect of pH and Oxygen Atom of the Hydrophobic Chain on the Self-Assembly Property and Morphology of the Pyridyl Boronic Acid Based Amphiphiles

Maiti

Roy

2013

Langmuir

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The surface activity and aggregation behavior of two synthesized boronic acid based anionic surfactants, sodium salt of 2-dodecyl pyridine-5-boronic acid (SDDPB) and sodium salt of 2-oxydodecyl pyridine-5-boronic acid (SODDPB), were studied in buffer solution at pH 9 and 13 containing carbohydrates. The self-assembly formation was investigated by use of a number of techniques including surface tension, conductivity, fluorescence spectroscopy, dynamic light scattering, X-ray diffraction, and transmission electron microscopy (TEM). Both of the amphiphiles exhibit a single break in the surface tension vs log(concentration) plots, indicating existence of one critical aggregation concentration. Steady state fluorescence spectroscopy was used to determine the polarity indexes using pyrene and the rigidity of the microenvironments of the aggregates using 1,6-diphenyl-1,3,5-hexatriene (DPH) as fluorescence probe molecules. The pKa's of both amphiphiles were determined in buffer solutions of different pH's. XRD studies were performed to shed light on the morphology of the self-assemblies. TEM micrographs revealed the existence of vesicles for both the amphiphiles in buffer solution of pH 9, but at pH 13, TEM pictures indicate the existence of closed vesicles in SDDPB solution and at concentrated solution the vesicles are fused to form sponge-like micelles. After aging the vesicular solution of pH 13 of SDDPB, the closed vesicles are destroyed. In contrast, for SODDPB at pH 13, TEM pictures suggest the existence of spherical and complex micelles in solution which were further transformed into crystal-like structure upon aging. The average hydrodynamic radii were determined by dynamic light scattering measurement. Therefore, for the first time, we have successfully synthesized two new surfactants containing pyridyl-boronic acid as a headgroup which shows remarkable tuning of morphology in two different pH's and in the presence of two different carbohydrates.

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“…There are five major groups of surfactants characterized by the charge of their polar moiety as a result of negatively or positively charged or nonionized functional groups: anionic, cationic, nonionic, amphoteric (zwitterionic), and semipolar. − …”

Section: Introductionmentioning

confidence: 99%

Surfactant-Mediated Effects on Hydrological and Physical Soil Properties: Data Synthesis

Lehmann,

Flaig,

Dueñas

et al. 2023

Environ. Sci. Technol.

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Soils are under the threat of a multitude of anthropogenic factors affecting the complex interplay of various physical and hydrological soil processes and properties. One such factor is the group of surface-active compounds. Surfactants have a broad range of applications and can reduce solid−liquid interfacial forces and increase wettability and dispersion of particles. Surfactant effects are context-dependent, giving rise to a wide range of reported effects on different soil processes and properties. Here, we evaluate the evidence base of surfactant research on 11 hydrological and physical soil variables. Our goal was to identify knowledge gaps and test the robustness of the proposed surfactant effects. We found that the current knowledge base is insufficient to reach strong data-backed conclusions about the effects of surfactants in soils. We identified a unique case of bias in the data as a result of conflated patterns from laboratory and field studies. We could not support the hypothesis that the surfactant charge determines soil effects for any of the tested soil variables. We believe that further experiments on surfactant-mediated effects on soil properties and processes are urgently required, paying attention, in particular, to improving experimental design and data reporting standards.

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First Example of Surfactants Enclosing a Semipolar Nitrogen−Boron Bond

Cited by 10 publications

References 16 publications

Pericyclic Reactions between Aminoboranes R₂BNR₂‘ and Alkenes: [4+2] vs [2+2] Transition States

Pericyclic Reactions between Aminoboranes R₂BNR₂‘ and Alkenes: [4+2] vs [2+2] Transition States

Effect of pH and Oxygen Atom of the Hydrophobic Chain on the Self-Assembly Property and Morphology of the Pyridyl Boronic Acid Based Amphiphiles

Surfactant-Mediated Effects on Hydrological and Physical Soil Properties: Data Synthesis

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First Example of Surfactants Enclosing a Semipolar Nitrogen−Boron Bond

Cited by 10 publications

References 16 publications

Pericyclic Reactions between Aminoboranes R2BNR2‘ and Alkenes: [4+2] vs [2+2] Transition States

Pericyclic Reactions between Aminoboranes R2BNR2‘ and Alkenes: [4+2] vs [2+2] Transition States

Effect of pH and Oxygen Atom of the Hydrophobic Chain on the Self-Assembly Property and Morphology of the Pyridyl Boronic Acid Based Amphiphiles

Surfactant-Mediated Effects on Hydrological and Physical Soil Properties: Data Synthesis

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Pericyclic Reactions between Aminoboranes R₂BNR₂‘ and Alkenes: [4+2] vs [2+2] Transition States

Pericyclic Reactions between Aminoboranes R₂BNR₂‘ and Alkenes: [4+2] vs [2+2] Transition States