4228-00-6Relevant articles and documents
Dodecanoic acid derivatives: Synthesis, antimicrobial evaluation and development of one-target and multi-target QSAR models
Sarova, Devinder,Kapoor, Archana,Narang, Rakesh,Judge, Vikramjeet,Narasimhan, Balasubramanian
experimental part, p. 769 - 781 (2012/05/20)
In this study a series of dodecanoic acid derivatives (1-30) were synthesized and evaluated for in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. 4-Nitro phenyl dodecanoate (4) and quinolin-8-yl dodecanoate (5) emerged as most effective antibacterial agents, and 1-(4-benzylpiperazin- 1-yl) dodecan-1-one (15) was found to be the most effective antifungal agent amongst the synthesized dodecanoic acid derivatives. Quantitative structure activity relationship (QSAR) studies performed by the development of one-target and multi-target models indicated that multitarget model was effective in describing the antimicrobial activity of dodecanoic acid derivatives as well demonstrated the importance of topological parameter, zero-order molecular connectivity index (0X). Springer Science+Business Media, LLC 2010.
Synthesis and critical micelle concentration of a series of gemini alkylphenol polyoxyethylene nonionic surfactants
Yang, Fang,Li, Gang,Xu, Nian,Liu, Rong,Zhang, Song-Mei,Wu, Zeng-Jiang
experimental part, p. 339 - 345 (2012/06/30)
A series of gemini n-alkylphenol polyoxyethylene surfactants (GAP) were successfully synthesized and their molecular structure were confirmed by NMR and FTIR spectrum. Using the same synthesis route, a Gemini nonylphenol polyoxyethylene surfactant (GNP) was synthesized using an industrial nonylphenol product and paraformaldehyde, and its molecular structure was also characterized by 1H-NMR and FTIR spectra. The optimal reaction conditions were established. The critical micelle concentration (CMC) values of GAP were determined by means of Wilhelmy plate method and steady-state fluorescence probe method. The experimental results show how the lengths of the hydrophilic polyoxyethylene chain and the hydrophobic tail alter the CMC values. The CMC values of the GAP are found to be much lower than those of corresponding conventional single tail nonionic surfactants of the polyethoxylated alkylphenol type, which indicates that the gemini species exhibit a better surface activity. AOCS 2011.
Reaction of carboxylic acid esters with phenolates in oil-in-water microemulsions based on cetyltrimethylammonium bromide
Mirgorodskaya,Valeeva,Kudryavtseva,Vylegzhanina,Zuev
, p. 590 - 595 (2008/02/08)
A kinetic study of reactions of carboxylic acid esters with phenols activated with alkalis or amines in microemulsions based on cationic surfactants showed that the phenolates formed upon activation exhibit different nucleophilicity depending on the value of the negative charge on the oxygen atom, which is determined by the properties of the phenol, ionizing agent, and solvent. Pleiades Publishing, Inc., 2006.
An eco-friendly method for the synthesis of aryl and alkyl esters of carboxylic acids using acid activated Indian bentonite
Vijayakumar,Iyengar, Pushpa,Nagendrappa, Gopalpur,Prakash, B. S. Jai
, p. 922 - 925 (2007/10/03)
Esterification of various carboxylic acids with phenol and alcohols has been achieved using acid activated Indian bentonite (AAIB) as catalyst. The catalyst is versatile, and the reaction is found to work well for primary, secondary and tertiary alcohols. The yields are very good under specific reaction conditions.
Effective Charge Development in Ester Hydrolysis Catalyzed by Cationic Micelles
Al-Awadi, Nouria,Williams, Andrew
, p. 2001 - 2004 (2007/10/02)
Reaction of hydroxide ion with substituted phenyl laurates is catalyzed by micelles containing CTAB (cetyltrimethylammonium bromide).The observed rate constants for ester consumption obey a Michaelis-Menten-like rate law, kobsd = (kOHKeq + kOHcat)/(Keq + ), where kOHcat is the second order rate constant for reaction of hydroxide ion with micelle-bound ester, Keq is a partition coefficient for dissociation of ester from the micelle-bound ester, and kOH is the second order rate constant for reaction of free ester with hydroxide ion.The value of the parameter Keq is independent of the nature of the substituent on the ester.The ratio kOHcat/Keq represents the free energy change from ester in aqueous solution to the transition state of the ester reaction in the micellar pseudophase.The dependence of log kOHcat/Keq on the pKa of the leaving phenol obeys a linear Bronsted equation with β1g = -0.51, and log kOH obeys a linear Bronsted equation with β1g = -0.56.Since both Bronsted parameters refer to catalyzed and uncatalyzed reactions starting from the same standard state (aqueous solution), the effective charge in the transtition state of both reactions is almost the same.The microscopic medium is thus similar for both cases, consistent with the COOAr moiety's residing in an aqueous-like region of the pseudophase in the catalytic process.
the Effect of Hydrophobic-Lipophilic Interactions on Chemical Reactivity. 1. New Evidence for Intermolecular Aggregation and Self-Coiling
Jiang, Xi-Kui,Hui, Yong-Zheng,Fan, Wei-Qiang
, p. 3839 - 3843 (2007/10/02)
The hydrolytic behavior of 21 para-substituted phenyl esters of n-alkanoic acids (n-X) with various chain lengths in 60:40 (Φ=0.60), 50:50 (Φ=0.50), and 40:60 v/v (Φ=0.40) Me2SO-H2O mixtures was studied.Four new sets of experimental results which include departure from Hammett correlation for N-hexadecanoates (16-X), substantial differences in activation parameters, and effects of amylose on the kinetic parameters and on the activation parameters are presented along lines of reasoning mentioned by previous authors.These data establish that the aggregation and self-coiling of the n-alkanoate chain actually exist under experimental conditions.
