Cleavage of 4-Nitrophenyl Diphenyl Phosphate by Isomeric Quaternary Pyridinium Ketoximes - How Can Structure and Lipophilicity of Functional Surfactants Influence Their Reactivity in Micelles and Microemulsions?

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Title:Cleavage of 4-Nitrophenyl Diphenyl Phosphate by Isomeric Quaternary Pyridinium Ketoximes - How Can Structure and Lipophilicity of Functional Surfactants Influence Their Reactivity in Micelles and Microemulsions?
Creators:
Kivala, Milan
Cibulka, Radek
Hampl, František
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 11-12, pp. 1642-1658
Uncontrolled Keywords:Phosphate esters cleavage, Pyridinium oximes, Functional surfactants, Nanoaggregates, Micelles, Microemulsions

Abstract

Amphiphilic pyridinium ketoximes 4-[1-(hydroxyimino)alkyl]-1-methylpyridinium bromides (<strong>1</strong>) and 1-alkyl-4-[1-(hydroxyimino)ethyl]pyridinium bromides (<strong>2</strong>) are isomeric cationic surfactants bearing the nucleophilic hydroxyimino group. They differ in the position of the nucleophilic function relative to polar head group and hydrophobic alkyl chain. The 4-nitrophenyl diphenyl phosphate (PNPDPP) cleavage by the oximate anions generated from <strong>1</strong> and <strong>2</strong> was used as a model reaction for the investigation of the influence of the structure and lipophilicity of functional surfactants on their reactivity in micelles and microemulsions. The investigation of the model reaction in cationic micelles of hexadecyltrimethylammonium bromide (CTAB), in non-ionic micelles (Triton X-100 and Brij 35) and in o/w microemulsion (isooctane/phosphate buffer/CTAB and butan-1-ol) has revealed that it is the lipophilicity which is the most important factor influencing the localization and reactivity of functional surfactants in nanoaggregates. <p>

Title:Cleavage of 4-Nitrophenyl Diphenyl Phosphate by Isomeric Quaternary Pyridinium Ketoximes - How Can Structure and Lipophilicity of Functional Surfactants Influence Their Reactivity in Micelles and Microemulsions?
Creators:
Kivala, Milan
Cibulka, Radek
Hampl, František
Uncontrolled Keywords:Phosphate esters cleavage, Pyridinium oximes, Functional surfactants, Nanoaggregates, Micelles, Microemulsions
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:71
Number:11-12
Page Range:pp. 1642-1658
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061642UNSPECIFIED
ID Code:2567
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Kivala, Milan; Cibulka, Radek; Hampl, František (2006) Cleavage of 4-Nitrophenyl Diphenyl Phosphate by Isomeric Quaternary Pyridinium Ketoximes - How Can Structure and Lipophilicity of Functional Surfactants Influence Their Reactivity in Micelles and Microemulsions? Collection of Czechoslovak Chemical Communications, 71 (11-12). pp. 1642-1658. ISSN 0010-0765

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