- Title
- Characterization of some amino acid derivatives of benzoyl isothiocyanate: Crystal structures and theoretical prediction of their reactivity
- 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/10962/447952
- Identifier
- vital:74686
- Identifier
- xlink:href="https://doi.org/10.1016/j.molstruc.2015.05.053"
- Description
- The reaction of benzoyl isothiocyanate with L-serine, L-proline, D-methionine and L-alanine gave 2-[(benzoylcarbamothioyl)amino]-3-hydroxypropanoic acid (I), 1-(benzoylcarbamothioyl)pyrrolidine-2-carboxylic acid (II), 2-[(benzoylcarbamothioyl)amino]-4-(methylsulfanyl)butanoic acid (III) and 2-[(benzoylcarbamothioyl)amino]propanoic acid (IV), respectively. The compounds have been characterized by IR, NMR, microanalyses and mass spectrometry. The crystal structures of all the compounds have also been discussed. Compound II showed rotamers in solution. DFT calculations of the frontier orbitals of the compounds have been carried out to ascertain the groups that contribute to the HOMO and LUMO, and to study their contribution to the reactivity of these compounds. The calculations indicated that the carboxylic acid group in these compounds is unreactive hence making the conversion to benzimidazoles via cyclization on the carboxylic acids impractical. This has been further confirmed by the reaction of compounds I–IV, respectively, with o-phenylene diamine which was unsuccessful but gave compound V.
- Format
- computer, online resource, application/pdf, 1 online resource (11 pages), pdf
- Publisher
- Elsevier
- Language
- English
- Relation
- Journal of Molecular Structure, Odame, F., Hosten, E.C., Betz, R., Lobb, K. and Tshentu, Z.R., 2015. Characterization of some amino acid derivatives of benzoyl isothiocyanate: Crystal structures and theoretical prediction of their reactivity. Journal of Molecular Structure, 1099, pp.38-48, Journal of Molecular Structure volume 1099 p. 38 2015 1872-8014
- 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
- Closed Access
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Lobb, Kevin Allan (Assoc Prof)
RU Department of Chemistry
SDG 03. Good Health and Well-Being
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