A novel gold (I)-mediated intramolecular transamidation of benzoyl thiourea derivatives to form benzamides via dethiocyanation
- Odame, Felix, Woodcock, Guillaume, Hosten, Eric C, Lobb, Kevin A, Tshentu, Zenixole R
- Authors: Odame, Felix , Woodcock, Guillaume , Hosten, Eric C , Lobb, Kevin A , Tshentu, Zenixole R
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/446988 , vital:74575 , xlink:href="https://doi.org/10.1016/j.jorganchem.2020.121359"
- Description: A novel gold(I)-mediated intramolecular transamidation of thiourea derivatives to yield benzamides via dethiocyanation have been achieved by the reaction of 3-(1,3-benzothiazol-2-yl)-1-(benzoyl)thiourea derivatives in the presence of gold(I) precursors. The compounds have been characterized using IR, NMR, GC-MS and microanalysis. The single crystal XRD of 3-(1,3-benzothiazol-2-yl)-1-(3-bromobenzoyl)thiourea (5), 3-(1,3-benzothiazol-2-yl)-1-(3-methoxybenzoyl)thiourea (6), N-(benzothiazol-2-yl)benzamide (10), N-(benzothiazol-2-yl)-3-chlorobenzamide (11), N-(benzothiazol-2-yl)-4-nitrobenzamide (12), N-(benzothiazol-2-yl)-3-bromobenzamide (14) have been discussed. The novel transformation is thought to proceed by a gold(I)-mediated intramolecular transamidation reaction which releases thiocyanate to yield the benzamide. Density functional theory calculations have been used to support the proposed mechanism for this transformation.
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- Authors: Odame, Felix , Woodcock, Guillaume , Hosten, Eric C , Lobb, Kevin A , Tshentu, Zenixole R
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/446988 , vital:74575 , xlink:href="https://doi.org/10.1016/j.jorganchem.2020.121359"
- Description: A novel gold(I)-mediated intramolecular transamidation of thiourea derivatives to yield benzamides via dethiocyanation have been achieved by the reaction of 3-(1,3-benzothiazol-2-yl)-1-(benzoyl)thiourea derivatives in the presence of gold(I) precursors. The compounds have been characterized using IR, NMR, GC-MS and microanalysis. The single crystal XRD of 3-(1,3-benzothiazol-2-yl)-1-(3-bromobenzoyl)thiourea (5), 3-(1,3-benzothiazol-2-yl)-1-(3-methoxybenzoyl)thiourea (6), N-(benzothiazol-2-yl)benzamide (10), N-(benzothiazol-2-yl)-3-chlorobenzamide (11), N-(benzothiazol-2-yl)-4-nitrobenzamide (12), N-(benzothiazol-2-yl)-3-bromobenzamide (14) have been discussed. The novel transformation is thought to proceed by a gold(I)-mediated intramolecular transamidation reaction which releases thiocyanate to yield the benzamide. Density functional theory calculations have been used to support the proposed mechanism for this transformation.
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Exploring intermolecular contacts in multi-substituted benzaldehyde derivatives: X-ray, Hirshfeld surface and lattice energy analyses
- Hulushe, Siyabonga T, Manyeruke, Meloddy H, Louzada, Marcel, Rigin, Sergei, Hosten, Eric C, Watkins, Gareth M
- Authors: Hulushe, Siyabonga T , Manyeruke, Meloddy H , Louzada, Marcel , Rigin, Sergei , Hosten, Eric C , Watkins, Gareth M
- Date: 2020
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/148483 , vital:38743 , DOI: 10.1039/C9RA10752E
- Description: Crystal structures of six benzaldehyde derivatives (1–6) have been determined and their supramolecular networks were established by an X-ray crystallographic study. The study has shown that the compounds are linked by various intermolecular interactions such as weak C–H⋯O hydrogen bonding, and C–H⋯π, π–π and halogen bonding interactions which consolidate and strengthen the formation of these molecular assemblies. The carbonyl group generates diverse synthons in 1–6 via intermolecular C–H⋯O hydrogen bonds. An interplay of C–H⋯O hydrogen bonds, and C–H⋯π and π–π stacking interactions facilitates the formation of multi-dimensional supramolecular networks. Crystal packings in 4 and 5 are further generated by type I halogen⋯halogen bonding interactions. The differences in crystal packing are represented by variation of substitution positions in the compounds. Structure 3 is isomorphous with 4 but there are subtle differences in their crystal packing.
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- Authors: Hulushe, Siyabonga T , Manyeruke, Meloddy H , Louzada, Marcel , Rigin, Sergei , Hosten, Eric C , Watkins, Gareth M
- Date: 2020
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/148483 , vital:38743 , DOI: 10.1039/C9RA10752E
- Description: Crystal structures of six benzaldehyde derivatives (1–6) have been determined and their supramolecular networks were established by an X-ray crystallographic study. The study has shown that the compounds are linked by various intermolecular interactions such as weak C–H⋯O hydrogen bonding, and C–H⋯π, π–π and halogen bonding interactions which consolidate and strengthen the formation of these molecular assemblies. The carbonyl group generates diverse synthons in 1–6 via intermolecular C–H⋯O hydrogen bonds. An interplay of C–H⋯O hydrogen bonds, and C–H⋯π and π–π stacking interactions facilitates the formation of multi-dimensional supramolecular networks. Crystal packings in 4 and 5 are further generated by type I halogen⋯halogen bonding interactions. The differences in crystal packing are represented by variation of substitution positions in the compounds. Structure 3 is isomorphous with 4 but there are subtle differences in their crystal packing.
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Synthesis, characterization and biological activity of some Dithiourea Derivatives:
- Odame, Felix, Hosten, Eric C, Krause, Jason, Isaacs, Michelle, Hoppe, Heinrich C, Khanye, Setshaba D, Sayed, Yasien, Frost, Carminita L, Lobb, Kevin A, Tshentu, Zenixole R
- Authors: Odame, Felix , Hosten, Eric C , Krause, Jason , Isaacs, Michelle , Hoppe, Heinrich C , Khanye, Setshaba D , Sayed, Yasien , Frost, Carminita L , Lobb, Kevin A , Tshentu, Zenixole R
- Date: 2020
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/163046 , vital:41007 , DOI: 10.17344/acsi.2019.5689
- Description: Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Autodock 4.2, synthesized and characterized by spectroscopic methods and microanalysis.
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- Authors: Odame, Felix , Hosten, Eric C , Krause, Jason , Isaacs, Michelle , Hoppe, Heinrich C , Khanye, Setshaba D , Sayed, Yasien , Frost, Carminita L , Lobb, Kevin A , Tshentu, Zenixole R
- Date: 2020
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/163046 , vital:41007 , DOI: 10.17344/acsi.2019.5689
- Description: Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Autodock 4.2, synthesized and characterized by spectroscopic methods and microanalysis.
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The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
- Hulushe, Siyabonga T, Manyeruke, Meloddy H, Hosten, Eric C, Kaye, Perry, Watkins, Gareth M
- Authors: Hulushe, Siyabonga T , Manyeruke, Meloddy H , Hosten, Eric C , Kaye, Perry , Watkins, Gareth M
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/194048 , vital:45418 , xlink:href="https://doi.org/10.1515/ncrs-2019-0698"
- Description: C11H8O4, monoclinic, P21/c (no. 14), a = 4.5947(2) Å, b = 10.5414(3) Å, c = 19.1611(7) Å, β = 94.084(2)°, V = 925.70(6) Å3, Z = 4, Rgt(F) = 0.0376, wRref(F 2) = 0.1109,T = 200(2) K.CCDC no.: 1906383
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- Authors: Hulushe, Siyabonga T , Manyeruke, Meloddy H , Hosten, Eric C , Kaye, Perry , Watkins, Gareth M
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/194048 , vital:45418 , xlink:href="https://doi.org/10.1515/ncrs-2019-0698"
- Description: C11H8O4, monoclinic, P21/c (no. 14), a = 4.5947(2) Å, b = 10.5414(3) Å, c = 19.1611(7) Å, β = 94.084(2)°, V = 925.70(6) Å3, Z = 4, Rgt(F) = 0.0376, wRref(F 2) = 0.1109,T = 200(2) K.CCDC no.: 1906383
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Ultrasound promoted synthesis, characterization and computational studies of some thiourea derivatives
- Odame, Felix, Hosten, Eric C, Lobb, Kevin A, Tshentu, Zenixole R
- Authors: Odame, Felix , Hosten, Eric C , Lobb, Kevin A , Tshentu, Zenixole R
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/451199 , vital:75028 , xlink:href="https://doi.org/10.1016/j.molstruc.2020.128302"
- Description: Synthesis of some thiourea derivatives have been achieved by using ultrasound, the compounds have been characterised using IR, NMR, GC-MS and elemental analysis. The single crystal X-ray structure of N-[(benzyloxy)methanethioyl]benzamide (IV), 1-benzoyl-3-(2-hydroxyethyl)thiourea (V) and 3-benzoyl-1-(1-benzylpiperidin-4-yl)thiourea (VI) has been presented and the bond lengths and bond angles contrasted with computed results. The HOMO and LUMO energy levels as well as the global chemical reactivity descriptors of the compounds have also been computed and discussed. Two comformers were obtained for compounds IV to VI in the molecular Electrostatic potential and the vibrational frequency computations and these have been discussed.
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- Authors: Odame, Felix , Hosten, Eric C , Lobb, Kevin A , Tshentu, Zenixole R
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/451199 , vital:75028 , xlink:href="https://doi.org/10.1016/j.molstruc.2020.128302"
- Description: Synthesis of some thiourea derivatives have been achieved by using ultrasound, the compounds have been characterised using IR, NMR, GC-MS and elemental analysis. The single crystal X-ray structure of N-[(benzyloxy)methanethioyl]benzamide (IV), 1-benzoyl-3-(2-hydroxyethyl)thiourea (V) and 3-benzoyl-1-(1-benzylpiperidin-4-yl)thiourea (VI) has been presented and the bond lengths and bond angles contrasted with computed results. The HOMO and LUMO energy levels as well as the global chemical reactivity descriptors of the compounds have also been computed and discussed. Two comformers were obtained for compounds IV to VI in the molecular Electrostatic potential and the vibrational frequency computations and these have been discussed.
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