1H NMR-based kinetic and theoretical studies of the simultaneous formation of two discrete rotameric systems of a novel difenchyl sulfite ester
- Singh, Alicia, Kaye, Perry T, Lobb, Kevin A
- Authors: Singh, Alicia , Kaye, Perry T , Lobb, Kevin A
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/447925 , vital:74684 , xlink:href="https://doi.org/10.1016/j.tet.2017.10.059"
- Description: Attempted repetition of a reported synthesis of fenchene from fenchol has afforded, in high overall yield, a mixture shown by spectroscopic and elemental analysis to comprise a pair of discrete rotameric systems of a novel 2-endo-2′-endo-difenchyl sulfite ester. The kinetics of the formation of these dimeric rotameric systems (I and II) has been explored experimentally, using 1H NMR spectroscopic analysis, and theoretically at molecular and quantum mechanical levels. Construction of a theoretical model has permitted calculation of rate constants for each of the steps, while modelling of the transition state complexes corresponding to the rate-determining steps for the formation of the rotameric systems I and II has revealed their independent access to further sets of interconverting rotamers.
- Full Text:
- Date Issued: 2017
- Authors: Singh, Alicia , Kaye, Perry T , Lobb, Kevin A
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/447925 , vital:74684 , xlink:href="https://doi.org/10.1016/j.tet.2017.10.059"
- Description: Attempted repetition of a reported synthesis of fenchene from fenchol has afforded, in high overall yield, a mixture shown by spectroscopic and elemental analysis to comprise a pair of discrete rotameric systems of a novel 2-endo-2′-endo-difenchyl sulfite ester. The kinetics of the formation of these dimeric rotameric systems (I and II) has been explored experimentally, using 1H NMR spectroscopic analysis, and theoretically at molecular and quantum mechanical levels. Construction of a theoretical model has permitted calculation of rate constants for each of the steps, while modelling of the transition state complexes corresponding to the rate-determining steps for the formation of the rotameric systems I and II has revealed their independent access to further sets of interconverting rotamers.
- Full Text:
- Date Issued: 2017
Synthesis and anti-parasitic activity of C-benzylated (N-arylcarbamoyl) alkylphosphonate esters
- Adeyemi, Christiana Modupe, Isaacs, Michelle, Mnkandhla, Dumisani, Krause, Rui W M, Klein, Rosalyn, Hoppe, Heinrich C, Lobb, Kevin A, Kaye, Perry T
- Authors: Adeyemi, Christiana Modupe , Isaacs, Michelle , Mnkandhla, Dumisani , Krause, Rui W M , Klein, Rosalyn , Hoppe, Heinrich C , Lobb, Kevin A , Kaye, Perry T
- Date: 2017
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/125641 , vital:35803 , https://doi.org/10.1016/j.tet.2017.01.045
- Description: Unexpected substituent-dependent regioselectivty challenges in the synthesis of C-benzylated (N-arylcarbamoyl)phosphonate esters have been resolved. The C-benzylated N-furfurylcarbamoyl derivative showed low micromolar PfLDH inhibition, while one of the C-benzylated N-arylcarbamoyl analogues was active against Nagana Trypanosoma brucei parasites which are responsible for African trypanosomiasis in cattle.
- Full Text:
- Date Issued: 2017
- Authors: Adeyemi, Christiana Modupe , Isaacs, Michelle , Mnkandhla, Dumisani , Krause, Rui W M , Klein, Rosalyn , Hoppe, Heinrich C , Lobb, Kevin A , Kaye, Perry T
- Date: 2017
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/125641 , vital:35803 , https://doi.org/10.1016/j.tet.2017.01.045
- Description: Unexpected substituent-dependent regioselectivty challenges in the synthesis of C-benzylated (N-arylcarbamoyl)phosphonate esters have been resolved. The C-benzylated N-furfurylcarbamoyl derivative showed low micromolar PfLDH inhibition, while one of the C-benzylated N-arylcarbamoyl analogues was active against Nagana Trypanosoma brucei parasites which are responsible for African trypanosomiasis in cattle.
- Full Text:
- Date Issued: 2017
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