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Proton affinity of diastereoisomers of modified prolines using the kinetic method and density functional theory calculations: role of the cis / trans substituent on the endo / exo ring conformation
Author(s) -
Mezzache S.,
Pepe C.,
Karoyan P.,
Fournier F.,
Tabet J.C.
Publication year - 2005
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2049
Subject(s) - chemistry , diastereomer , substituent , density functional theory , computational chemistry , kinetic energy , stereochemistry , physics , quantum mechanics
Abstract 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. Copyright © 2005 John Wiley & Sons, Ltd.