title: Conformational analysis and intramolecular interactions of L-proline methyl ester and its N-acetylated derivative through spectroscopic and theoretical studies.
abstract: This work reports a detailed study regarding the conformational preferences of L-proline methyl ester (ProOMe) and its N-acetylated derivative (AcProOMe) to elucidate the effects that rule their behaviors, through nuclear magnetic resonance (NMR) and infrared (IR) spectroscopies combined with theoretical calculations. These compounds do not present a zwitterionic form in solution, simulating properly amino acid residues in biological media, in a way closer than amino acids in the gas phase. Experimental (3)JHH coupling constants and infrared data showed excellent agreement with theoretical calculations, indicating no variations in conformer populations on changing solvents. Natural bond orbital (NBO) results showed that hyperconjugative interactions are responsible for the higher stability of the most populated conformer of ProOMe, whereas for AcProOMe both hyperconjugative and steric effects rule its conformational equilibrium.
authors.affiliation: Physical Organic Chemistry Laboratory, Chemistry Institute, University of Campinas , 13083-970 Campinas, SP, Brazil.
authors.forename: Carolyne B
authors.initials: CB
authors.lastname: Braga
authors.forename: Lucas C
authors.initials: LC
authors.lastname: Ducati
authors.forename: Cláudio F
authors.initials: CF
authors.lastname: Tormena
authors.forename: Roberto
authors.initials: R
authors.lastname: Rittner
mesh_terms: D000107:Acetylation; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011789:Quantum Theory
chemical_list: C071203:acryloylproline methyl ester; D011392:Proline