NMR Spectroscopy E-Book
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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Serie: EMR Books
- Sprache: Englisch
The challenges faced by environmental scientists today are vast, complex, and multi-faceted. For instance, predicting the fate of an environmental pollutant or understanding ecosystem responses to climate change, necessitate a firm understanding of molecular structure and dynamics of environmental media as well as the components that exist and interact within this media. Furthermore, linking information obtained at the molecular-scale to ecosystem-level processes is a major pursuit of modern environmental research. As such, NMR spectroscopy and its scalability from the molecular-scale to the macroscopic-scale, is facilitating rapid growth in environmental science. In addition, the versatility of NMR spectroscopy has resulted in the development and implementation of different types of NMR techniques to examine the structure of various types of environmental samples, living and non-living, as well as the study of critical environmental processes. This comprehensive handbook is a collection of chapters that span from methods to how NMR is used in environmental research to gain insight into various ecosystem properties. It is organized into three parts: * Part A focuses on methods used in environmental NMR which span from solution-state to magnetic resonance imaging. * Part B emphasizes how NMR spectroscopy plays an essential role in understanding various types of environmental components and related processes, including different forms of organic matter found in soil, water, and air as well as how NMR is used to probe the fate of water, organic pollutants, and metals in the environment. * Part C focuses on the growing field of environmental metabolomics which uses NMR as its main discovery platform. This volume highlights the immense potential of NMR spectroscopy to expand our fundamental understanding of environmental processes and how it will continue to do so well into the future. About eMagRes Handbooks eMagRes (formerly the Encyclopedia of Magnetic Resonance) publishes a wide range of online articles on all aspects of magnetic resonance in physics, chemistry, biology and medicine. The existence of this large number of articles, written by experts in various fields, is enabling the publication of a series of eMagRes Handbooks on specific areas of NMR and MRI. The chapters of each of these handbooks will comprise a carefully chosen selection of eMagRes articles. In consultation with the eMagRes Editorial Board, the eMagRes handbooks are coherently planned in advance by specially-selected Editors, and new articles are written to give appropriate complete coverage. The handbooks are intended to be of value and interest to research students, postdoctoral fellows and other researchers learning about the scientific area in question and undertaking relevant experiments, whether in academia or industry. Have the content of this handbook and the complete content of eMagRes at your fingertips! Visit: href="http://www.wileyonlinelibrary.com/ref/eMagRes">www.wileyonlinelibrary.com/ref/eMagRes
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Table of Contents
Cover
eMagRes Handbooks
Title Page
Copyright
eMagRes
International Advisory Board
Contributors
Series Preface
Preface
Abbreviations and Acronyms
Part A: Fundamentals of Environmental NMR
Chapter 1: Environmental NMR: Solution-State Methods
1.1 Introduction
1.2 General NMR Characteristics of Nuclei across the Periodic Table
1.3 Classical NMR Observables
1.4 Practical Aspects Related to Sensitivity and Resolution in Complex Mixtures
1.5 General Characteristics of Higher Dimensional NMR Spectra of Environmental Mixtures
1.6 The Nature of Environmental Samples
1.7 NMR Analysis of Functional Groups in Environmental Organic Mixtures
1.8 Examples
1.9 Conclusion and Future Trends
References
Chapter 2: Environmental NMR: Diffusion Ordered Spectroscopy Methods
2.1 Introduction
2.2 Translational Diffusion
2.3 Pulsed-Gradient Spin-Echo (PGSE) and Diffusion Ordered Spectroscopy (DOSY)
2.4 Applications
2.5 Future of NMR Diffusion Methods in this Field
Related Articles in Emagres
References
Chapter 3: Environmental NMR: Hyphenated Methods
3.1 Introduction
3.2 Preparation of Environmental Samples
3.3 Liquid Chromatography Nuclear Magnetic Resonance
3.4 Liquid Chromatography Solid-Phase Extraction Nuclear Magnetic Resonance
3.5 Applications of LC-NMR to Environmental Samples
3.6 Conclusions
Acknowledgment
Related Articles in eMagRes
References
Chapter 4: Environmental NMR: Solid-State Methods
4.1 Introduction
4.2 Basic Techniques for Environmental Solid-state NMR
4.3 Acquiring and Processing Spectra
4.4 Toward Quantitative Reliability
4.5 Using More Complex Pulse Sequences
4.6 Nitrogen-15 NMR
Related Articles in eMagRes
References
Further Reading
Chapter 5: Environmental NMR: High-resolution Magic-angle Spinning
5.1 Introduction
5.2 Experimental Methods
5.3 Representative Applications to Environmental Science
5.4 Conclusions
Acknowledgments
Related Articles in eMagRes
References
Further Reading
Chapter 6: Environmental Comprehensive Multiphase NMR
6.1 Introduction
6.2 NMR Spectroscopy of Natural Samples
6.3 Molecular Structure in Natural Materials Using CMP-NMR
6.4 Molecular Interactions
6.5 Conclusions and Future Directions
Acknowledgments
Related Articles in eMagRes
References
Chapter 7: Environmental NMR: Magnetic Resonance Imaging
7.1 Introduction
7.2 NMR Properties of Environmental Materials
7.3 Considerations of Equipment and Methodology
7.4 Some Selected Applications of MRI in Environmental Science
7.5 Future Trends and Challenges
Acknowledgments
Related Articles in EmagRes
References
Chapter 8: Environmental NMR: Fast-field-cycling Relaxometry
8.1 Introduction
8.2 The FFC NMR Relaxometry Experiment in Practice
8.3 Elaboration of the Decay/Recovery Curves for Natural Systems
8.4 From
τ
Domain to
T
1
Domain: The Inverse Laplace Transformation and the Relaxograms
8.5 The Nuclear Magnetic Resonance Dispersion Profiles: Quantitative Aspects in Environmental Applications
8.6 The Motion Regimes and the Qualitative Aspects of NMRD Profiles in Environmental Applications and Green Chemistry
8.7 Conclusions and Future Perspectives
Acknowledgment
References
Chapter 9: Mobile NMR
9.1 Introduction
9.2 Single-Sided NMR
9.3 Closed Magnets
9.4 Conclusion
Acknowledgments
Related Articles in eMagRes
References
Chapter 10: Terrestrial Magnetic Field NMR: Recent Advances
10.1 Introduction
10.2 Geophysical Applications
10.3 Imaging
10.4 Spectroscopy
10.5 Future Directions
Related Articles in eMagRes
References
Part B: NMR for Air, Soil and Water
Chapter 11: Dissolved Organic Matter
11.1 Introduction
11.2 Characterization of DOM Using Solid-state NMR Spectroscopy
11.3 Characterization of DOM Using Solution-state NMR Spectroscopy
11.4 NMR as a Complementary Analytical Technique for DOM Characterization
11.5 Conclusions and Future Research Directions
Acknowledgments
References
Chapter 12: Atmospheric Organic Matter
12.1 Introduction
12.2 Setting the Scene
12.3 Solid-state NMR Studies of Atmospheric Organic Matter
12.4 Solution-state NMR Studies of Atmospheric Organic Matter
12.5 The Quest for Quantification and Source Apportionment
12.6 Conclusions
Acknowledgments
Related Articles in eMagRes
References
Chapter 13: Soil Organic Matter
13.1 Introduction
13.2 A Few Milestones in the History of Nuclear Magnetic Resonance Spectroscopy
13.3 Changing Perception of Soil Organic Matter through Time
13.4 Conclusions and Future Prospects
Related Articles in eMagRes
References
Chapter 14: Chemical Ecology
14.1 Introduction
14.2 NMR-based Identification and Structure Elucidation of Ecologically Relevant Compounds
14.3 NMR-based Mixture Analysis
14.4 NMR-based Cell-Type-specific Localization
14.5 NMR-based Biosynthetic and Metabolic Labeling Studies
14.6 NMR Detection of the Metabolic Modification of Plant Polymers
14.7 Summary and Conclusions
Acknowledgments
Related Articles in eMagRes
References
Further Readings
Chapter 15: Forest Ecology and Soils
15.1 Introduction
15.2 Organic Matter Inputs to Forest Soils
15.3 Organic Matter Pools in Forest Soils
15.4 Tracing Organic Matter Fluxes through Forest Ecosystems
15.5 Forest Response to Disturbance
15.6 Overall Experimental Considerations
15.7 Conclusions
Acknowledgments
Related Article in eMagRes
References
Chapter 16: Biofuels
16.1 Introduction
16.2 NMR in Prospecting for Raw Materials
16.3 NMR in Production Control
16.4 NMR in Quality Control of the Finished Product
16.5 Conclusions and Future Challenges
Related Articles in eMagRes
References
Further Readings
Chapter 17: Clay Minerals
17.1 Introduction
17.2 Clay Mineral Structure
17.3 NMR Studies of Clay Minerals
17.4 Studies of Surfaces, Interlayers, and Adsorbed Species
17.5 NMR Studies of Surface Reactivity of Clay Minerals
17.6 Conclusions
Acknowledgments
References
Chapter 18: Soil–Water Interactions
18.1 Introduction
18.2 Relaxation Times (
T
1
and
T
2
) in Porous Systems
18.3 NMR Spectroscopy to Study Water Mobility and Water Binding
18.4 Water in Wet Soils
18.5 Soil–Water Interactions at Low Water Contents: Supramolecular Water Networks
18.6 Conclusions and Outlook
Acknowledgment
Related Articles in eMagRes
References
Further Readings
Chapter 19: Metals in the Environment
19.1 Introduction
19.2 General Metal NMR Spectroscopy
19.3 Selected Literature Examples
19.4 Potential Experiments
19.5 Conclusions and Outlook
Acknowledgments
Related Articles in eMagRes
References
Chapter 20: Organic Pollutants in the Environment
20.1 Introduction
20.2 Mechanistic Studies of Contaminant Fate
20.3 Analytical Studies
20.4 Conclusions
References
Chapter 21: Soil–Plant–Atmosphere Continuum Studied by MRI*
21.1 Introduction
21.2 Mapping Transport and Related Parameters in the SPAC by MRI Approaches
21.3 Hardware for in situ Plant Studies
Related Articles in eMagRes
References
Part C: NMR and Environmental Metabolomics
Chapter 22: Environmental Metabolomics
22.1 Introduction
22.2 Background
22.3 Rationale
22.4 Techniques
22.5 Current Applications
22.6 The Future
References
Chapter 23: Environmental Metabolomics: NMR Techniques
23.1 Introduction
23.2 One-Dimensional (1D) NMR Techniques
23.3 Two-dimensional (2D) NMR Techniques
23.4 Metabolite Identification and Quantification
23.5 Future Directions and Conclusions
Acknowledgments
Related Articles in eMagRes
References
Chapter 24: Environmental Metabolomics of Soil Organisms
24.1 Introduction
24.2 NMR-Based Metabolomics in Environmental Soil Science
24.3 Ecotoxicology
24.4 NMR and Metabolomics in the Study of Natural Products
24.5 Potential Limitations of Metabolomics
24.6 Conclusions
Acknowledgments
References
Chapter 25: Environmental Metabolomics of Aquatic Organisms
25.1 Introduction
25.2 Initial Studies and Major Contributors to the Field
25.3 Environmental Metabolomics
25.4 Conclusion
Related Articles in eMagRes
References
Chapter 26: Metabolomics in Environmental Microbiology
26.1 Introduction
26.2 NMR Methods for Environmental Metabolomics of Microbes
26.3 Case Studies
26.4 Conclusions and Prospects
Acknowledgments
Related Articles in eMagRes
References
Chapter 27: Plant Metabolomics
27.1 Introduction
27.2 Sample Preparation for NMR Analysis
27.3 Spectral Normalization and Alignment
27.4 Hyphenated NMR Approaches for Plant Metabolomics
27.5 2D NMR Approaches for Quantitative Plant Metabolomics
27.6 Stable Isotope Monitoring and Flux Analysis
27.7 NMR Imaging and MRI for Plant Metabolism Studies
Acknowledgments
Related Articles in eMagRes
References
Index
End User License Agreement
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Guide
Cover
Table of Contents
Series Preface
Preface
Part A: Fundamentals of Environmental NMR
Chapter 1: Ab Initio
List of Illustrations
Figure 1.1
Figure 1.2
Figure 1.3
Figure 1.4
Figure 1.6
Figure 1.7
Figure 1.8
Figure 1.9
Figure 1.10
Figure 1.11
Figure 2.1
Figure 2.2
Figure 2.3
Figure 2.4
Figure 2.5
Figure 2.6
Figure 2.7
Figure 2.8
Figure 2.9
Figure 2.10
Figure 2.11
Figure 2.12
Figure 3.1
Figure 3.2
Figure 3.3
Figure 3.4
Figure 3.5
Figure 3.6
Figure 3.7
Figure 3.8
Figure 3.9
Figure 3.10
Figure 3.11
Figure 3.12
Figure 3.13
Figure 4.1
Figure 4.2
Figure 4.3
Figure 4.4
Figure 4.5
Figure 4.6
Figure 5.1
Figure 5.2
Figure 5.3
Figure 5.4
Figure 5.5
Figure 5.6
Figure 5.7
Figure 5.8
Figure 5.9
Figure 5.10
Figure 5.11
Figure 5.12
Figure 6.1
Figure 6.2
Figure 6.3
Figure 6.4
Figure 6.5
Figure 6.6
Figure 6.7
Figure 6.8
Figure 6.9
Figure 6.10
Figure 6.11
Figure 6.12
Figure 6.13
Figure 6.14
Figure 7.1
Figure 7.2
Figure 7.3
Figure 7.4
Figure 7.5
Figure 7.6
Figure 7.7
Figure 8.1
Figure 8.2
Figure 8.3
Figure 8.4
Figure 8.5
Figure 8.6
Figure 8.7
Figure 9.1
Figure 9.2
Figure 9.3
Figure 9.4
Figure 9.5
Figure 9.6
Figure 9.7
Figure 9.8
Figure 9.9
Figure 9.10
Figure 10.1
Figure 10.2
Figure 10.3
Figure 10.4
Figure 10.5
Figure 11.1
Figure 11.2
Figure 11.3
Figure 11.4
Figure 11.5
Figure 12.1
Figure 12.2
Figure 12.3
Figure 12.4
Figure 13.1
Figure 13.2
Figure 13.3
Figure 13.4
Figure 13.5
Figure 14.1
Figure 14.2
Figure 14.3
Figure 14.4
Figure 14.5
Figure 14.6
Figure 14.7
Figure 14.8
Figure 14.9
Figure 14.10
Figure 14.11
Figure 14.12
Figure 14.13
Figure 15.1
Figure 15.2
Figure 15.3
Figure 15.4
Figure 16.1
Figure 16.2
Figure 16.3
Figure 16.4
Figure 16.5
Figure 16.6
Figure 16.7
Figure 16.8
Figure 17.1
Figure 17.2
Figure 17.3
Figure 17.4
Figure 17.5
Figure 17.6
Figure 17.7
Figure 17.8
Figure 17.9
Figure 17.10
Figure 17.11
Figure 18.1
Figure 18.2
Figure 18.3
Figure 18.4
Figure 18.5
Figure 18.6
Figure 19.1
Figure 19.2
Figure 19.3
Figure 19.4
Figure 19.5
Figure 19.6
Figure 19.7
Figure 20.1
Figure 20.2
Figure 20.3
Figure 21.1
Figure 21.4
Figure 21.2
Figure 21.3
Figure 23.1
Figure 23.2
Figure 23.3
Figure 23.4
Figure 23.5
Figure 23.6
Figure 24.1
Figure 24.2
Figure 24.3
Figure 25.1
Figure 25.2
Figure 26.1
Figure 26.2
Figure 26.3
Figure 27.1
Figure 27.2
List of Tables
Table 1.1
Table 1.2
Table 1.4
Table 4.1
Table 4.2
Table 4.3
Table 4.4
Table 5.1
Table 5.2
Table 5.3
Table 16.1
Table 17.1
Table 18.1
Table 18.2
Table 19.1
Table 20.1
Table 23.1
Table 23.2
Table 26.1
Table 26.2
eMagRes Handbooks
Based on eMagRes (formerly the Encyclopedia of Magnetic Resonance), this monograph series focuses on hot topics and major developments in modern magnetic resonance and its many applications. Each volume in the series will have a specific focus in either general NMR or MRI, with coverage of applications in the key scientific disciplines of physics, chemistry, biology or medicine. All the material published in this series, plus additional content, will be available in the online version of eMagRes, although in a slightly different format.
Previous eMagRes Handbooks
NMR
Crystallography
Edited by Robin K. Harris, Roderick E. Wasylishen, Melinda J.~Duer
ISBN 978-0-470-69961-4
Multidimensional
NMR Methods for the Solution State
Edited by Gareth A. Morris, James W.~Emsley
ISBN 978-0-470-77075-7
Solid-State NMR Studies of Biopolymers
Edited by Ann E. McDermott, Tatyana Polenova
ISBN 978-0-470-72122-3
NMR
of Quadrupolar Nuclei in Solid Materials
Edited by Roderick E. Wasylishen, Sharon E. Ashbrook, Stephen Wimperis
ISBN 978-0-470-97398-1
RF
Coils for MRI
Edited by John T. Vaughan, John R. Griffiths
ISBN 978-0-470-77076-4
MRI
of Tissues with Short T
2
s or T
2
*s
Edited by Graeme M. Bydder, Gary D. Fullerton, Ian R. Young
ISBN 978-0-470-68835-9
eMagRes
Edited by Robin K. Harris, Roderick E. Wasylishen, Edwin D. Becker, John R. Griffiths, Vivian S. Lee, Ian R. Young, Ann E. McDermott, Tatyana Polenova, James W. Emsley, George A. Gray, Gareth A. Morris, Melinda J.~Duer and Bernard C. Gerstein.
The eMagRes (formerly EMR) is based on the original printed Encyclopedia of Nuclear Magnetic Resonance, which was first published in 1996 with an update volume added in 2000. eMagRes was launched online in 2007 with all the material that had previously appeared in print. New updates have since been and will be added on a regular basis throughout the year to keep the content up to date with current developments. Nuclear was dropped from the title to reflect the increasing prominence of MRI and other medical applications. This allow the editors to expand beyond the traditional borders of NMR to MRI and MRS, as well as to EPR and other modalities. eMagRes covers all aspects of magnetic resonance, with articles on the fundamental principles, the techniques and their applications in all areas of physics, chemistry, biology and medicine for both general NMR and MRI. Additionally, articles on the history of the subject are included.
For more information see: www.wileyonlinelibrary.com/ref/eMagRes
NMR Spectroscopy: A Versatile Tool for Environmental Research
Editors
Myrna J. Simpson
University of Toronto, Toronto, Ontario, Canada
André J. Simpson
University of Toronto, Toronto, Ontario, Canada
This edition first published 2014 © 2014 John Wiley & Sons Ltd
Registered office
John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex,PO19 8SQ, United Kingdom
For details of our global editorial offices, for customer services and for information abouthow to apply for permission to reuse the copyright material in this book please see ourwebsite at www.wiley.com.
The right of the authors to be identified as the authors of this work has been asserted inaccordance with the Copyright, Designs and Patents Act 1988.
All rights reserved. No part of this publication may be reproduced, stored in aretrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by the UK Copyright, Designsand Patents Act 1988, without the prior permission of the publisher.
Wiley also publishes its books in a variety of electronic formats. Some content thatappears in print may not be available in electronic books.
Designations used by companies to distinguish their products are often claimed astrademarks. All brand names and product names used in this book are trade names, service marks, trademarks or registered trademarks of their respective owners. Thepublisher is not associated with any product or vendor mentioned in this book. Thispublication is designed to provide accurate and authoritative information in regard to thesubject matter covered. It is sold on the understanding that the publisher is not engagedin rendering professional services. If professional advice or other expert assistance isrequired, the services of a competent professional should be sought.
Library of Congress Cataloging-in-Publication Data
NMR spectroscopy : a versatile tool for environmental research / editors Myrna J. Simpson, Andre J. Simpson.
pages cm
Includes bibliographical references and index.
ISBN 978-1-118-61647-5 (cloth)
1. Nuclear magnetic resonance spectroscopy. 2. Environmental chemistry.
I. Simpson, Myrna J., editor. II. Simpson, Andre J., editor. TD193N57 2014 577’.140154366--dc23
2014012695
A catalogue record for this book is available from the British Library.
ISBN-13: 978-1-118-61647-5
eMagRes
Editorial Board
Editors-in-Chief
Robin
K. Harris
University of Durham
Durham
UK
Roderick
E. Wasylishen
University of Alberta
Edmonton, Alberta
Canada
Section Editors
SOLID-STATE NMR & PHYSICS
Melinda
J. Duer
University of Cambridge
Cambridge
UK
SOLUTION-STATE NMR & CHEMISTRY
George
A. Gray
Varian Inc.
Palo Alto, CA
USA
Gareth
A. Morris
University of Manchester
Manchester
UK
BIOCHEMICAL NMR
Ann
E. McDermott
Columbia University
New York, NY
USA
Tatyana
Polenova
University of Delaware
Newark, DE
USA
MRI & MRS
John
R. Griffiths
Cancer Research UK
Cambridge Research Institute
Cambridge
UK
Ian
R. Young
Imperial College
London
UK
HISTORICAL PERSPECTIVES
Edwin
D. Becker
National Institutes of Health
Bethesda, MD
USA
International Advisory Board
David
M. Grant (Chairman) (deceased)
University of Utah Salt Lake City, UT
USA
Robin
K. Harris (Chairman – from January 2014)
University of Durham
Durham
UK
Isao
Ando
Tokyo Institute of Technology
Tokyo
Japan
Adriaan
Bax
National Institutes of Health Bethesda, MD
USA
Chris
Boesch
University of Bern
Bern
Switzerland
Paul
A. Bottomley
Johns Hopkins University Baltimore, MD
USA
William
G. Bradley
UCSD Medical Center San Diego, CA
USA
Graeme
M. Bydder
UCSD Medical Center San Diego, CA
USA
Paul
T. Callaghan (deceased)
Victoria University of Wellington
Wellington
New Zealand
James
W. Emsley
University of Southampton
Southampton
UK
Richard
R. Ernst
Eidgenössische Technische Hochschule (ETH)
Zürich
Switzerland
Ray
Freeman
University of Cambridge
Cambridge
UK
Lucio
Frydman
Weizmann Institute of Science
Rehovot
Israel
Bernard
C. Gerstein
Ames, IA
USA
Maurice
Goldman
Villebon sur Yvette
France
Harald
Günther
Universität Siegen
Siegen
Germany
Herbert
Y. Kressel
Harvard Medical School Boston, MA
USA
C.
Leon Partain
Vanderbilt University Medical Center
Nashville, TN
USA
Alexander
Pines
University of California at Berkeley
Berkeley, CA
USA
George
K. Radda
University of Oxford
Oxford
UK
Hans
Wolfgang Spiess
Max-Planck Institute of Polymer Research
Mainz
Germany
Charles
P. Slichter
University of Illinois at Urbana-Champaign
Urbana, IL
USA
John
S. Waugh
Massachusetts Institute of Technology (MIT)
Cambridge, MA
USA
Bernd
Wrackmeyer
Universität Bayreuth
Bayreuth
Germany
Kurt
Wüthrich
The Scripps Research Institute La Jolla, CA
USA
and
ETH Zürich
Zürich
Switzerland
Contributors
Giuseppe Alonzo
Dipartimento di Scienze Agrarie e Forestali, Università degli Studi di Palermo, 90128 Palermo, Italy
Chapter 8: Environmental NMR: Fast-field-cycling Relaxometry
Brian Andrew
Bruker BioSpin Corporation, Billerica, MA 01821–3991, USA
Chapter 6: Environmental Comprehensive Multiphase NMR
Gregory A. Barding Jr
Department of Chemistry, University of California, Riverside, Riverside, CA 92521, USA
Chapter 27: Plant Metabolomics
Thomas Baumann
Institute of Hydrochemistry, Technische Universität München, D-81377 Munich, Germany
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Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
Lesen Sie weiter in der vollständigen Ausgabe!
