Synthesis and properties of highly lipophilic phosphazene bases

Selberg, Sigrid; Rodima, Toomas; Lõkov, Märt; Tshepelevitsh, Sofja; Haljasorg, Tõiv; Chhabra, Shibba Takkar; Kadam, Sandip A.; Toom, Lauri; Vahur, Signe; Leito, Ivo

doi:10.1016/j.tetlet.2017.04.039

Cited by 11 publications

(14 citation statements)

References 16 publications

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“…The newly obtained values are generally in good agreement with those published earlier , , . For 78 % of bases the differences are less than 0.03 p K a units and for 98 % of bases less than 0.1 p K a units.…”

Section: Resultssupporting

confidence: 91%

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On the Basicity of Organic Bases in Different Media

et al. 2019

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The basicities of simple organic bases – aliphatic and aromatic amines, amidines, phosphazenes, as well as saturated and unsaturated nitrogen heterocycles – are examined in acetonitrile, dimethyl sulfoxide, tetrahydrofuran, water and the gas phase. The basicities (pKaH values) of conjugate acids of a large variety of bases in these media are presented and discussed. Equations employing easily usable structural descriptors have been derived for approximately converting basicities from acetonitrile to other solvents. Recommendations are given on their practical use and a number of pKaH values that are experimentally unavailable are estimated from these relationships. An important part of the minireview is a large compilation of pKaH and GB values of the compounds in solvents and the gas phase, respectively, as well as the revised basicity scale in acetonitrile, now containing more than 270 pKaH values.

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Section: Resultssupporting

confidence: 91%

“…The revised basicity scale (Table ) is composed of previously published data, , and unpublished results for 9‐chloroacridine and 2‐aminoacridine (experimental conditions as in ref …”

Section: Methodsmentioning

confidence: 99%

On the Basicity of Organic Bases in Different Media

et al. 2019

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“…Synthesis and characterization of the used lipophilic bases have been described elsewhere. [9] In addition, phosphazene 4-NO2-C6H4-P1(pyrr) [10] was included as a reference compound, having comparatively different structure and directly measured aqueous pKa value. The rest of the used chemicals were of commercial origin: acetonitrile (Rathburn, HPLC grade, used for preparing stock solutions of base B), octan-1-ol (Sigma-Aldrich, Chromasolv grade), glycine (Reanal, analytical reagent), p-toluenesulfonic acid monohydrate (Sigma-Aldrich, ACS reagent, ˃98.5 %), sodium p-toluenesulfonate (Reakhim, "pure"), HBr (Fisher, 48 %, ACS reagent), NaCl (Fisher, ACS reagent) and NaBr (Fisher, ACS reagent).…”

Section: Methodsmentioning

confidence: 99%

“…Aqueous pKa (a) pKa ow Counterion 1 7.7 [9] 4.3 Cl -2 8.4 [9] 5.4 Cl -3 9.2 [9] 6.7 Cl -4 10.2 [9] 8.2 Cl -4-NO2-C6H4-P1(pyrr) 9.22 [10] 6.4…”

Section: Compoundmentioning

confidence: 99%

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Biphasic pKa Values

Selberg¹,

Tshepelevitsh²,

Leito³

2018

Croat. Chem. Acta

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A novel approach-termed here as biphasic pKa values-is presented for quantifying the acidity/basicity of lipophilic compounds embedded in water-immiscible media (membranes or solutions) at equilibrium with aqueous solution. In this approach the hydrogen ion activity is determined in the aqueous phase, while the concentration ratio of protonated and deprotonated forms of acid/base is measured in the lipophilic phase with any suitable technique. The approach has been demonstrated on the example of biphasic pKa values of some lipophilic indicator bases in the octanol : water system, measured using UV-Vis spectrophotometry. The measurement is straightforward if the counterion identity and concentration and overall ionic strength in the aqueous phase are included in the standard state definition. Biphasic pKa values are envisaged to be useful for characterizing lipophilic indicators, synthetic receptors, phase transfer catalysts and other implements that are used in hydrophobic media (e.g. in sensor membranes) in contact with water.

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Tris(benzophenoneimino)phosphane and Related Compounds

et al. 2023

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A new group of bases with benzophenoneiminyl (bpi) moiety has been synthesized and characterized in this work. The title compound tris(benzophenoneimino)phosphane (P(bpi) 3 ) 1 was prepared with a convenient one-pot approach: benzophenone imine was deprotonated using MeMgCl and reacted with PBr 3 in diglyme. The method could be considered as a method of choice for preparing other (amino)phosphanes in case lithiointermediates and/or protonated phosphane is out of consideration. Phosphane 1 is further used to prepare a range of related phosphonium cations and phosphazenes. Phosphonium cations were deprotonated to assess the stability of the resulting phosphonium ylides. In some cases, the bulky substances were capable of forming PÀ N heterocycles. Experimental (MeCN) and computational (MeCN, THF, gas-phase) basicities of benzophenone imine, phosphane 1, phosphonium ylides, and phosphazenes, as well as some representative XRD structures, are presented and discussed.

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Synthesis and properties of highly lipophilic phosphazene bases

Cited by 11 publications

References 16 publications

On the Basicity of Organic Bases in Different Media

On the Basicity of Organic Bases in Different Media

Biphasic pKa Values

Tris(benzophenoneimino)phosphane and Related Compounds

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