Pair-Wise Interactions by Gas Chromatography; Part III:<sup>1,2</sup>Synthesis of Isosteric Stationary Phases for Gas Chromatography

Cloux, R.; Défayes, Guy; Foti, K.; Dutoit, Jean-Claude; Kováts, Ervin sz.

doi:10.1055/s-1993-25968

Cited by 19 publications

(4 citation statements)

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“…A suspension of EtO-Py-NO 2 , (975 mg, 5.3 mmol), K 2 CO 3 (21.970 g, 159 mmol), and Bu 4 N + Br – (1.7 mg, 0.0053 mmol) in acetonitrile (15 mL) was added dropwise to a solution of Br(CH 2 ) 11 OBn (2.184 mg, 6.4 mmol) in acetonitrile (15 mL). After 96 h the residue was washed with HCl (1 M) and then with aqueous sodium hydrogen carbonate, dried over Na 2 SO 4 , and filtered.…”

Section: Methodsmentioning

confidence: 99%

Sugar–Oligoamides: Synthesis of DNA Minor Groove Binders

2012

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Sugar-oligoamides have been designed and synthesized as structurally simple carbohydrate-based ligands to study carbohydrate-minor groove DNA interactions. Here we report an efficient solution-phase synthetic strategy to obtain two broad families of sugar-oligoamides. The first type, structure vector A (-Py[Me]-γ-Py-Ind), has a methyl group present as a substituent on the nitrogen of pyrrole B, connected to the C terminal of the oligoamide fragment. The second type, structure vector B (-Py[(CH(2))(11)OH]-γ-Py-Ind), has an alkyl chain present on the nitrogen of pyrrole B connected to the C terminal of the oligoamide fragment and has been designed to access to di- and multivalent sugar-oligoamides. By using sequential DIPC/HOBt coupling reactions, the oligoamide fragment -Py[R]-γ-Py-Ind has been constructed. The last coupling reaction between the anomeric amino sugar and the oligoamide fragment was carried out by activating the acid derivative as a BtO- ester, which has been performed by using TFFH. The isolated esters (BtO-Py[R]-γ-Py-Ind) were coupled with selected amino sugars using DIEA in DMF. The synthesis of two different selective model vectors (vector A (1) and vector B (2)) and two types of water-soluble sugar-oligoamide ligands, with vector A structure (compounds 3-7) and with vector B structure (compound 8), was carried out.

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Section: Methodsmentioning

confidence: 99%

Sugar–Oligoamides: Synthesis of DNA Minor Groove Binders

2012

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“…Two of the derivatives were formed by replacing one of the CH 3 groups of C78 by OH 18,23‐dioctadecylhentetracontan‐1‐ol (POH) group and CN 1‐cyano‐18,23‐dioctadecylhentetracontane (PCN) group, and the other two solvents were formed by replacing all the four CH 3 groups of C78 by four CF 3 19,24‐bis(18,18,18‐trifluorooctadecyl)‐1,1,1,42,42,42‐hexafluorodotetracontane (TTF) groups and four OCH 3 17,22‐bis‐(16‐methoxyhexadecyl)‐1,38‐dimethoxyoctatriacontane (TMO) groups. Chemical procedures to prepare these derivatives were reported in the literature 23. Because of the dominating size of the hydrocarbon backbone, the five solvents have similar structures, and nearly the same density, molar volume, and thermal expansion coefficient.…”

Section: Probe Dependency Of χ23 Of Mixtures Of C78 and Derivativesmentioning

confidence: 99%

Probe dependency of flory–huggins interaction parameters between solvents: Cases of hydrocarbons and isosteric derivatives

Huang

2012

J of Applied Polymer Sci

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Inverse gas chromatography has been widely used to determine the Flory-Huggins parameter, v, between two solvents. Many studies showed that interaction parameters were probe dependent. In recent studies, it was proposed that the interaction between two solvents may lead to different contact probability between solutes and solvent mixtures and create an apparent solubility parameter different from volume average rule. An equation was previously derived to relate the probe dependency to the deviation of solubility parameter from the volume average rule. By plotting / 2 / 3 RT(v 23 /V 2 ) versus the solubility parameter of solutes, a linear trend could be observed with a negative slope for miscible mixtures. When there was an unfavorable interaction between two solvents, an opposite situation would be observed. In this study, mixtures of 19,24-dioctadecyldotetracontane (C78) and its derivatives were tested. The solubility parameters of mixtures showed negative deviation from the volume average. The plots of / 2 / 3 RT(v 23 /V 2 ) versus solubility parameter of solutes had positive slopes. For two derivatives the best estimated values of RT(v 23 /V 2 ) were negative in certain temperatures. Enthalpy-entropy compensation plot showed that these two derivatives have higher entropy of mixing. Mixtures Enthalpy-Entropy relation TMO (1/2) RTv 23,S /V 2 ¼ À0.84 RTv 23,H /V 2 À0.41 PCN (1/2) RTv 23,S /V 2 ¼ À0.87 RTv 23,H /V 2 À1.77 TTF (1/2) RTv 23,S /V 2 ¼ À0.90 RTv 23,H /V 2 þ 2.50 POH (1/3) RTv 23,S /V 2 ¼ À0.94 RTv 23,H /V 2 þ 1.67 POH (2/3) RTv 23,S /V 2 ¼ À0.92 RTv 23,H /V 2 þ 2.20 ARTICLE 5006

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“…The stationary phases used were derivatives of a branched paraffin, C78H158 (19,24-dioctadecyldotetracontane, C78), where a methyl or ethyl group of the paraffin was replaced by: OH (18,23-dioctadecyl-l-untetracontanol, POH), CN (1-cyano-18,23-dioctadecyluntetracontane, PCN), OCH3 (1 -methoxy-17,22-dioctadecyltetracontane, MMO), and SH (18,23-dioctadecyl-1-untetracontethiol, PSH) groups. The solvents were synthesized by Cloux et al [6,7] and their formal structures are given in Figure 1. The purity of the liquid stationary phases was greater than 99 % as determined by 13C and 1H NMR spectroscopy.…”

Section: -Chloro-alkanes Aromatics 2-alkanones; --: Calculated By mentioning

confidence: 99%

Measurement of Henry coefficients by capillary columns coated with slightly polar solvents

2000

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SummaryThe specific retention volumes and Henry coefficients measured on packed columns are compared with those calculated via retention indices determined on wall coated open tubular capillary columns. The stationary phase liquids used were derivatives of a branched paraffin, C7~H158, where a methyl or ethyl group of the paraffin was replaced by OH, CN, OCH 3 and SH groups. The retention indices of a series of molecular probes of varying polarity (aromatics, 1-chloroalkanes, 1-acetoxy-alkanes, 1-alkanols, 2-alkanones) were determined at T = 403.15 K on fused-silica open tubular columns prepared by static coating that gave stable and uniform solvent films. After obtaining the absolute data on packed columns for n-alkanes, the specific retention volumes and Henry coefficients of the solutes were calculated. The retention data obtained on both columns showed good agreement.

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Pair-Wise Interactions by Gas Chromatography; Part III:^1,2Synthesis of Isosteric Stationary Phases for Gas Chromatography

Cited by 19 publications

References 0 publications

Sugar–Oligoamides: Synthesis of DNA Minor Groove Binders

Sugar–Oligoamides: Synthesis of DNA Minor Groove Binders

Probe dependency of flory–huggins interaction parameters between solvents: Cases of hydrocarbons and isosteric derivatives

Measurement of Henry coefficients by capillary columns coated with slightly polar solvents

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Pair-Wise Interactions by Gas Chromatography; Part III:1,2Synthesis of Isosteric Stationary Phases for Gas Chromatography

Cited by 19 publications

References 0 publications

Sugar–Oligoamides: Synthesis of DNA Minor Groove Binders

Sugar–Oligoamides: Synthesis of DNA Minor Groove Binders

Probe dependency of flory–huggins interaction parameters between solvents: Cases of hydrocarbons and isosteric derivatives

Measurement of Henry coefficients by capillary columns coated with slightly polar solvents

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Pair-Wise Interactions by Gas Chromatography; Part III:^1,2Synthesis of Isosteric Stationary Phases for Gas Chromatography