Proton affinity of diastereoisomers of modified prolines using the kinetic method and density functional theory calculations: role of thecis/trans substituent on theendo/exo ring conformation
| Autor: | Françoise Fournier, Philippe Karoyan, S. Mezzache, Jean-Claude Tabet, Claude Pepe |
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| Rok vydání: | 2005 |
| Předmět: |
Models
Molecular Proline Hydrogen bond Stereochemistry Organic Chemistry Molecular Conformation Diastereomer Substituent Glutamic Acid Stereoisomerism Protonation Ring (chemistry) Analytical Chemistry Kinetics chemistry.chemical_compound chemistry Leucine Thermodynamics Proton affinity Density functional theory Algorithms Spectroscopy Cis–trans isomerism |
| Zdroj: | Rapid Communications in Mass Spectrometry. 19:2279-2283 |
| ISSN: | 1097-0231 0951-4198 |
| Popis: | The proton affinity (PA) of cis/trans-3-prolinoleucines and cis/trans-3-prolinoglutamic acids have been studied by the kinetic method and density functional theory (DFT) calculations. Several conformations of the neutral and the protonated modified prolines, in particular the endo and exo ring conformations, were analyzed with respect to their contribution to the PA values. When the substituent is an alkyl, both the diastereoisomers have the same PA value. However, the PA values for the diastereoisomers are different when the substituted chain contains functional groups (e.g. a carboxyl group). This variation in PA values could be attributed to the existence of intramolecular hydrogen bonds. |
| Databáze: | OpenAIRE |
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