Preparation of a Novel Class of Cationic Gemini Imidazolium Surfactants Containing Amide Groups as the Spacer: Their Surface Properties and Antimicrobial Activity

Abstract

A class of novel cationic Gemini imidazolium surfactants containing amide groups as the spacer were synthesized from ethylenediamine and 1‐bromoalkane(C8, C10, C12, C14, C16) by N‐alkylation to get N,N′‐dialkyl ethylenediamine (1a–e), 1a–e was further reacted with chloroacetyl chloride by N‐acylation to get N,N′‐(ethane‐1,2‐diyl)bis(2‐chloro‐N‐alkylacetamide) (2a–e), which was further reacted respectively with 1‐methyl imidazole by quaternized to form the surfactant molecule, N,N′‐((ethane‐1,2‐diyl)bis(alkyl‐azanediyl)bis(2‐oxoethane‐2,1‐diyl)) bis(1‐methyl‐1H‐imidazol‐3‐ium) dichloride. The structures of intermediates (1a–e) and (2a–e) were characterized by IR and 1H NMR. The structures of the surfactants (3a–e) were characterized by IR, 1H‐NMR and 13C‐NMR and element analysis. The critical micelle concentrations (CMC) of 3a–e were determined by the conductivity method at 25 °C. The CMC values decreased with increasing the length of the hydrophobic chain. The surfactants (3a–e) showed good foaming stability, emulsion ability and wetting ability. The surfactants (3a–e) also have good antimicrobial activity against Staphylococcus aureus, Escherichia coli and Bacillus subtilis.

Aggregation behavior of anionic sulfonate gemini surfactants with dodecylphenyl tails

“…Because micelles have a much larger hydrodynamic radius than individual molecules of the surfactant, the diffusion of the molecules through a solution is more sluggish and they are less efficient charge carriers. Above the CMC, the conductivity continues to increase with the surfactant concentration; however, the slope is lower above than below the CMC [42]. Consequently, the formation of micelles in a solution is manifested as visible break in the plot of conductivity versus surfactant concentration.…”

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

“…In this regard, the imidazolium skeleton can be transformed into ionic liquids with promisingly potent pharmacological properties [ 18 , 19 , 20 , 21 ]. Consequently, monoimidazolium [ 22 , 23 , 24 ] and bisimidazolium [ 25 , 26 , 27 , 28 ] salts have been explored as a new generation of antibacterial agents. In this context, amino acid-based monoimidazolium salts with good bacterial toxicity have been reported in the literature [ 29 ].…”

Flexible Semicrown Ether‐Linked Symmetric Cationic Gemini Surfactants: Synthesis and Evaluation as Catalysts for Acceleration of Diastereoselective [3 + 2] Cycloaddition Reaction in Reversed Phase Micellar Media

“…The emulsification is realized by the effect of adsorption, and it forms a layer of adsorptive film in the interface of dispersed droplets. As is shown in Table , the emulsion power of compound 2b is better than 2a because adsorption at the interface increases with the increase of the molecular hydrophobic chain length (Wang et al, ; Xu et al, ).…”