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Zeitschrift für Physikalische Chemie

International journal of research in physical chemistry and chemical physics

Editor-in-Chief: Rademann, Klaus


IMPACT FACTOR 2017: 1.144
5-year IMPACT FACTOR: 1.144

CiteScore 2017: 1.08

SCImago Journal Rank (SJR) 2017: 0.495
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Volume 223, Issue 4-5

Issues

Conformation and Aggregation of Proline Esters and Their Aromatic Homologs: Pyramidal vs. Planar RR´N-H in Hydrogen Bonds

Susanne Hesse / Martin A. Suhm
Published Online: 2009-09-25 | DOI: https://doi.org/10.1524/zpch.2009.6043

Abstract

The conformations of proline esters are investigated by infrared spectroscopy in supersonic slit jet expansions. Two easily convertible puckering variants of the pyrrolidine ring with intramolecular N-H···O contacts are shown to be particularly stable. The aggregation tendency of proline esters via intermolecular N-H···O hydrogen bonds is remarkably weak. IR differences between enantiopure and racemic dimers are difficult to quantify. Dehydrogenation of the pyrrolidine ring to pyrrole leads to a stable planar carboxylic ester conformation. Its aggregation tendency is pronounced due to the planar hybridization of the nitrogen atom and leads to a symmetric, β sheet-like dimer with strongly red-shifting hydrogen bonds. The spectroscopic observations underscore the differences between intermolecular interactions of N-terminal and peptide-bound amino acids in peptide chains.

Keywords: Proline Esters; Pyramidal RR´N-H; Planar RR´N-H; Hydrogen Bonds

About the article

* Correspondence address: Universität Göttingen, Institut für Physikalische Chemie, Tammannstr. 6, 37077 Göttingen, Deutschland,


Published Online: 2009-09-25

Published in Print: 2009-05-01


Citation Information: Zeitschrift für Physikalische Chemie, Volume 223, Issue 4-5, Pages 579–604, ISSN (Online) 2196-7156, ISSN (Print) 0942-9352, DOI: https://doi.org/10.1524/zpch.2009.6043.

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[1]
Katharina E. Otto, Susanne Hesse, Tobias N. Wassermann, Corey A. Rice, Martin A. Suhm, Thorsten Stafforst, and Ulf Diederichsen
Physical Chemistry Chemical Physics, 2011, Volume 13, Number 31, Page 14119
[2]
Johan J. J. Dom, Benjamin J. van der Veken, Bart Michielsen, Sam Jacobs, Zhifeng Xue, Susanne Hesse, Hans-Martin Loritz, Martin A. Suhm, and Wouter A. Herrebout
Physical Chemistry Chemical Physics, 2011, Volume 13, Number 31, Page 14142
[3]
Bart Michielsen, Johan J. J. Dom, Benjamin J. van der Veken, Susanne Hesse, Zhifeng Xue, Martin A. Suhm, and Wouter A. Herrebout
Physical Chemistry Chemical Physics, 2010, Volume 12, Number 42, Page 14034
[4]
M. A. Suhm and F. Kollipost
Physical Chemistry Chemical Physics, 2013, Volume 15, Number 26, Page 10702
[5]
Juhyon J. Lee, Merwe Albrecht, Corey A. Rice, Martin A. Suhm, Anke Stamm, Manuel Zimmer, and Markus Gerhards
The Journal of Physical Chemistry A, 2013, Volume 117, Number 32, Page 7050
[6]
Bart Michielsen, Johan J. J. Dom, Benjamin J. van der Veken, Susanne Hesse, Martin A. Suhm, and Wouter A. Herrebout
Physical Chemistry Chemical Physics, 2012, Volume 14, Number 18, Page 6469

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