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Carbon Nanotubes: Properties and Applications
Published in Alexander V. Vakhrushev, Vladimir I. Kodolov, A. K. Haghi, Suresh C. Ameta, Carbon Nanotubes and Nanoparticles, 2019
The functionalization of nanotubes is carried out by using carboxylic groups, which acts as a precursor for most esterification and amidation reactions. The carboxylic group is converted into an acyl chloride with the use of thionyl or oxalyl chloride which is then reacted with the desired amide, amine, or alcohol. CNTs modified with acyl chloride react readily with highly branched molecules such as poly(amidoamine), which acts as a template for silver ion and later being reduced by formaldehyde. Amino-modified CNTs can be prepared by reacting ethylene diamine with an acyl chloride-functionalized CNTs. In a similar way, thiol-stabilized ZnS-capped CdSe QDs were protected with 2-aminoethanethiol and linked to the acid-terminated CNTs in presence of a coupling agent such as 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (Fig. 10.9).31
Carboxylic Acids, Carboxylic Acid Derivatives, and Acyl Substitution Reactions
Published in Michael B. Smith, A Q&A Approach to Organic Chemistry, 2020
An acid chloride has a chlorine attached directly to a carbonyl (Cl—C=O). What is the IUPAC nomenclature system for an acid chloride?
Synthesis and characterization of the Co(II) and Ni(II) complexes of 1,3,4-thiadiazole-derived ketones and secondary alcohols: thermal and magnetic properties
Published in Journal of Coordination Chemistry, 2021
Melih Erdogan, Kubra Kiymaz, Hakan Tahtaci, Saban Uysal
In the second step of the study, N-(5-((2-(3,4-dichlorophenyl)-2-oxoethyl)thio)-1,3,4-tiadiazole-2-yl)benzamide derivatives (5a-j) were synthesized by reaction of 3 with various benzoyl chloride derivatives (4a-j) in the presence of pyridine with yields varying between 65% and 84%. These reactions are typical nucleophilic acyl substitution reactions that occur through nucleophilic addition and elimination to the carbonyl carbon. Acyl groups produce substitution reactions, as expected. Chlorine that has bonded to the carbonyl carbon can be removed by protonation if necessary. Acyl chlorides usually react by losing the chloride ion, a very good leaving group. The lone electron pair on the amino group in 3 attacks the carbonyl carbon of the acyl derivatives (4a-j) as a nucleophile. A proton from the amino group transfers to chloride and the electron pair on oxygen attacks the carbon to form a double bond, with hydrogen chloride turning into pyridinium chloride salt. After the reaction is completed, when the raw materials formed are washed with a large amount of water, pyridinium chloride is removed from the medium. The proposed reaction mechanism for formation of 5a-j is given in Figure 2.
An expedient and rapid green chemical synthesis of N-chloroacetanilides and amides using acid chlorides under metal-free neutral conditions
Published in Green Chemistry Letters and Reviews, 2018
Chloroacetyl chloride (CAC) (26) is an important two carbon bifunctional unit widely used in synthetic chemistry (27). It is used as a protecting group (28) for alcohols and amines. The acid chloride part is used in many acylation reactions with alcohols, amines, (29–32) alkynes (33) and also in Friedel–Crafts reactions (34, 35). Similarly the α-chlorine can be replaced by many nucleophiles (OH─, NH2─, SH─ etc.) through SN2 displacement (36–39). Many chloroacetamides are used as herbicides such as alachlor [15972-60-8], metolachlor [51218-45-2].
Anthracene possessing amide functionality as a turn-on fluorescent probe for Cu2+ and Zn2+ ions
Published in Journal of Coordination Chemistry, 2021
The procedure for synthesis of A1 is outlined in Scheme 1. Initially acyl chloride 1 was synthesized by taking 9-anthracene carboxylic acid (0.8 gm, 3.8 mmol) and one drop of N,N-dimethylformamide in 3 ml of thionyl chloride in a vacuum dried two neck round bottom flask. After the reaction was complete (4-5 h), the in situ generated HCl was removed with a gas trap apparatus containing KOH pallets and excess of N,N-dimethylformamide was removed by vacuum. This formed acyl chloride (1) was further used without purification.