- Title
- Benzimidazole or Diamide From a Reaction of Diamines and Carboxylic Acids or Acid Chlorides: Crystal Structures and Theoretical Studies
- Creator
- Odame, Felix, Hosten, Eric C, Betz, Richard, Lobb, Kevin A, Tshentu, Zenixole R
- Subject
- To be catalogued
- Date
- 2015
- Type
- text
- Type
- article
- Identifier
- http://hdl.handle.net/10962/447938
- Identifier
- vital:74685
- Identifier
- xlink:href="https://pdfs.semanticscholar.org/bf5a/ce94c9436f40059793eb988e08da8ef09886.pdf"
- Description
- A reaction of an acid chloride with a diamine yielded a diamide. m-Toluic acid was chlorinated to m-toluoyl chloride and subsequently reacted with 4-methyl-o-phenylenediamine in pyridine to obtain 3-methyl-N-[2-(3-methylbenzamido)phenylbenzamide (I). 2-(3-Methylphenyl)-1H-benzimidazole (II) has been obtained upon reacting o-phenylenediamine with m-toluic acid in polyphosphoric acid and toluene. The compounds have been characterized by IR, NMR, microanalyses and GC-MS. The crystal structures of the compounds have been discussed. DFT calculations of the frontier orbitals of the precursor compounds have been carried out to ascertain the groups that contribute to the HOMO and LUMO, and to study their contribution to the reactivity in the formation of the diamides and benzimidazoles. The synthesis of the amide from a diamine was seen to be favoured in the presence of a good leaving group attached to the carbonyl as in the case of acid chloride. However, the synthesis of benzimidazoles was found to be favoured in the presence of an excess of a protonating agent and high temperature.
- Format
- computer, online resource, application/pdf, 1 online resource (9 pages), pdf
- Publisher
- Acta Chimica Slovenica
- Language
- English
- Relation
- Acta Chimica Slovenica, Odame, F., Hosten, E., Betz, R., Lobb, K. and Tshentu, Z.R., 2015. Benzimidazole or Diamide From a Reaction of Diamines and Carboxylic Acids or Acid Chlorides: Crystal Structures and Theoretical Studies. Acta Chimica Slovenica, 62(4), Acta Chimica Slovenica volume 62 number 4 2015 1580-3155
- Rights
- Publisher
- Rights
- Use of this resource is governed by the terms and conditions of the Elsevier Terms and Conditions Statement (https://www.elsevier.com/legal/elsevier-website-terms-and-conditions)
- Rights
- Open Access
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Collections
Lobb, Kevin Allan (Assoc Prof)
RU Department of Chemistry
SDG 03. Good Health and Well-Being
| Thumbnail | File | Description | Size | Format | |||
|---|---|---|---|---|---|---|---|
| View Details Download | SOURCE1 | Benzimidazole or Diamide From a Reaction.pdf | 318 KB | Adobe Acrobat PDF | View Details Download |