کتاب Basic One- and Two-Dimensional NMR Spectroscopy انگلیسی

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Fourth, Completely Revised and Updated Edition

Translated by: Jack K. Becconsall

Prof. Dr. Horst Friebolin
Organisch-Chemisches Institut der Universitat
Im Neuenheimer Feld 270
69120 Heidelberg
Germany

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors , and publisher do not warrant the information contained in these books , including this book, to be free of e rrors . Readers are advised to keep in mind that stateme nts, data, illustrations, procedural detail s or other items may inadvertently be inaccurate.

Foreword

Over the past decade, many, if not most, graduate students and postdoctoral fellows in organic chemistry seem to have come to regard nuclear magnetic resonance spectroscopy as a “black box” . Something in which you insert an unknown and out comes the data to establish structural formula. Perhaps this trend in the way NMR is perceived is really not surprising, because how manufacturers have tried to package their instruments to be ” user friendly” and because of the enormous growth in the sophistication of what NMR instrumentation can do.

Those of us who were fortunate to be in on the beginning of the applications of NMR to organic chemistry in the mid- 1950’s were able to more or less “grow” with the field and come into the modern arena of multipulse and multidimensional NMR with substantial experience with NMR fundamentals. Those who now wish to start using NMR in their research surely must feel, at least somewhat, overwhelmed by the enormity and sophistication of the currently available knowledge of NMR and must have further concerns at being told by the specialists, that fantastic further, even more sophisticated , developments are in the offing. A “black box” that would function with no need to worry about its inner workings must then be an attractive proposition. The problem is that to properly use modern NMR requires a lot of rather specialized knowledge. The effects of couplings , of exchange, of relaxation times, of low sensitivity, of solvent and so on, make selection of instrumental parameters for taking spectra far from routine. Serious errors or inefficient use of very expensive instrumentation come with ease.

The best way to learn NMR spectroscopy is by doing it , but textbooks, guidebooks anet:J:eference books are vitally necessary. Having written two b oks about NMR basics, with a third in progress , I know mething about the difficulties of making available “what e ery NMR user should know” . And it is to this objective th Professor Friebolin has made a wonderfully broad coRtfi ution. This book will be of interest and help to both those needing to learn and those needing a reference book to refresh their memories, or extend their capabilities in NMR spectroscopy. It is not a book intended to replace the treatises of Abragam or Bodenhausen, Ernst and Wokaun.

However, even though it does start at a useful elementary level , it goes rather deeply into the difficult basics of multipulse and multidimensional spectroscopy. The result is material that almost every reader will find of value.

The beginner can start with the elements of chemical shifts and couplings and later proceed to more difficult matters. The expert can find ways of explaining what he is doing , without necessarily resorting to density matrices; or else , in impatience with an eager, but dull , learner, can say “Go read about it in Friebolin , then we can talk” .

Much is covered in this book in meaningful detail. There is a plethora of structural parameters for proton and carbon NMR and many examples of how they can be used . Best of all , though , are very clear, meticulously written descriptions of INEPT, DEPT, INADEQUATE, COSY, NOESY, and the like , in one- and two-dimensional NMR spectroscopy. Experts may prefer mathematical equations for compactness and “it is easy to see”. I prefer descriptions such as those used by Professor Friebolin , which will indeed require careful reading , rereading and drawing and redrawing ones own vector diagrams, but can lead to a real level of understanding. Such understanding in its turn can only result in improved ability to take and interpret NMR spectra.

1-The Physical Basis of NMR Spectroscopy

1-1 Introduction

In 1946 two research groups, that of F. Bloch, W.W. Hansen and M. E. Packard and that of E. M. Purcell, H. C. Torrey and R.V. Pound, independently observed nuclear magnetic reso nance signals for the first time. Bloch and Purcell were jointly awarded the Nobel Prize for Physics in 1952 for their discovery. Since then nuclear magnetic resonance (NMR) spectroscopy has developed into an indispensable tool for chemists, bio chemists, physicists, and more recently medical scientists.

During the first three decades of NMR spectroscopy all measure ments relied on one-dimensional modes of observation; this gives spectra having just one frequency axis, the second axis being used to display the signal intensities. The development of two-dimensional NMR experiments during the 1970s heralded the start of a new era in NMR spectroscopy. Spectra recorded by these methods have two frequency axes, the intensities being displayed in the third dimension. More recently it has even become possible to perform experiments with three or more dimensions, although these are still far from being routine techniques.

The importance of the position that NMR spec troscopy now occupies is illustrated by the awards of the Nobel Prize for Chemistry in 1991 to R.R. Ernst and in 2002 to K. Wi.ithrich, and of the Nobel Prize for Medicine in 2003 to P. Lauterbur and P. Mansfield for their pioneering research on NMR methods in chemistry, biochemistry and medicine. The new techniques that have emerged during the last few years show that developments in NMR spectroscopy are still far from coming to an end.

This book aims to explain why it is that, for chemists espe cially, NMR spectroscopy has become {possibly) the most important of aJJ spectroscopic methods.

The main field of application of NMR spectroscopy is that of determining the structures of molecules. The necessary infor mation for this is obtained by measuring, analyzing and inter preting high-resolution NMR spectra recorded on liquids of low viscosity (or in some cases on solids by using special tech niques and instruments that have been developed in the last few years). In this book we will confine our attention almost exclusively to high-resolution NMR spectroscopy on liquids, since solid-state measurements involve quite different experimental techniques and the interpretation often brings in extra compli cations.

The nuclides that mainly interest us are protons (1H) and car bon-13 (‘³C), as their resonances are the most important ones for determining the structures of organic molecules. However, in the following chapters we shall meet also examples of NMR spectroscopy of other nuclides whose NMR signals can now be observed without difficulty.

In order to understand NMR spectroscopy we first need to learn how nuclei which have a nuclear angular momentum P and a magnetic momentµ behave in a static magnetic field. Following this we shall discuss the basic NMR experiment, the different methods of observation, and the spectra] parameters.

1	The Physical Basis of NMR Spectroscopy	1
1.1	ntroduction	1
1.2	Nuclear Angular Momentum and Magnetic Moment	2
1.3	Nuclei in a Static Magnetic Field	4
1.3.1	Directional Quantization	4
1.3.2	Energy of the Nuclei in the Magnetic Field	4
1.3.3	Populations of the Energy Levels	6
1.3.4	Macroscopic Magnetization ………….. .	6
1.4	Basic Principles of the NMR Experiment …. .	7
1.4.1	ThReesonance Condition …………… .	7
1.4.2	Basic Principle of the NMR Measurement … .	8
1.5	The Pulsed NMR Method …………… .	9
1.5.l	The Pulse ………………………. .	9
1.5.2	The Pulse Angle ………………….. .	10
1.5.3	Relaxation ……………………… .	13
1.5.4	The Time and Frequency Domains: the Fourier Transformation	14
1.5.5	Spectrum Accumulation …………….. .	16
1.5.6	The Pulsed NM R Spectrometer …………	18
1.6	Spectral Parameters: a Brief Survey .……. .	22
1.6.l	The Chemical Shift. ……………….. .	22
1.6.1.1	Nuclear Shielding …………………. .	22
1.6.1.2	Reference Compounds and the a-Scale …… .	24
1.6.2	Spin-Spin Coupling………………… .	26
1.6.2.1	The Indirect Spin-Spin Coupling …………	26
1.6.2.2	Coupling to One Neighboring Nucleus (AX Spin System)	27
1.6.2.3	Coupling to Two Equivalent Neighboring Nuclei (AX2 Spin System)	29
1.6.2.4	Coupling to Three or More Equivalent Neighboring Nuclei (AXn Spin System)	30
1.6.2.5	Multiplicity Rules …………………. .	30
l.6.2.6	Couplings between Three Non-equivalent Nuclei (AMX Spin System)	31
1.6.2.7	Couplings between Equivalent Nuclei (A., Spin Systems)	32
1.6.2.8	The Order of a Spectrum ……………..	33
1.6.2.9	Couplings between Protons and other Nuclei: 13C Satellite Spectra	33
1.6.3	The Intensities of the Resonance Signals	34
1.6.3.l	1H Signal Intensities	34
1.6.3.2	1·1cs1·gna1·1ntens1.t.1es	35
1.6.4	Summary	37
1.7	“Other” Nuclides	38
1.7.I	Nuclides with Spin/= 1/2	39
1.7.2	Nuclides with Spin 1 > 112	40
1.8	Bibliography for Chapter 1	41
2	The Chemical Shift	43
2.1	ntroduction	43
2. 1.l	Influence of the Charge Density on the Shielding	44
2.12	Effects of Neighboring Groups	47
2.1.2.1	Magnetic Anisotropy of Neighboring Groups	47
2. 1.2 .2	Ring Current Effects	49
2. 1.2 .3	Electric Field Effects	51
2. 1.2.4	Intermolecular Inte ractions – Hydrogen Bonding and Solvent Effects	51
2.1.2.5	Isotope Effects	51
2..1.3	Summary	52
2.2	1 H Chemical Shifts of Organic Compounds	53
2.2.1	Alkanes and Cycloalkanes	54
2.2.2	Alkenes	56
2.2.3	Arenes	56
2.2.4	Alkynes	57
2.2.5	Aldehydes	58
2.2.6	OH, SH , NH	59
2.3	13C Chemical Shifts of Organic Compounds	60
2.3.l	Alka nes and Cycloalkanes	61
2.3.2	Alkenes	63
2.3.3	Arenes	64
2.3.4	Alkynes	66
2.3.5	Allenes	66
2.3.6	Carbonyl and Carboxy Compounds	66
2.3.6.1	Aldehydes and Ketones	67
2.3.6.2	Carboxylic Acids and Derivati ves	68
2.4	Relationships between the Spectrum and the Molecular Structure	70
2.4. 1	Equivalence, Symmetry a nd Chi ra li ty	70
2.4 .2	Homotopic, Enantiotopic and Diaste reotopic Groups	74
2.4.3	Summary	77
2.5	Chemical Shifts of “Other” Nuclides	78
2.6	Bibliography for Chapter 2	83
3	Indirect Spin-Spin Coupling	85
3.1	Introduction	85
3.2	H,H Coupling Constants and Chemical Structure	87
3.2. l	Geminal Couplings ²./ (H,H)	87
3.2.1.1	Dependence on Bond Angle	87
3.2. l.2	Substituent Effects	88
3.2.l.3	Effects of Neighboring iT-Electrons	88
3.2.2	Yicinal Couplings 3./(H,H)	89
3.2.2.1	Dependence on the Dihedral Angle	90
3.2.2.2	Substituent Effects	93
3.2.3	H,H Couplings in Aromatic Compounds	95
3.2.4	Long-range Couplings	96
3.3	C,H Coupling Constants and Chemical Structure	97
3.3.1	C,H Couplings through One Bond 1J(C,H)	97
3.3.l.l	Dependence on the s-Fraction	97
3.3.1.2	Substituent Effects	97
3.3.2	C,H Couplings through Two or More Bonds	98
3.3.2.I	Geminal Couplings (i.e. ²1 (C,H) in H-C- 13C)	98
3.3.2.2	Yicinal Couplings (i.e. 3J(C,H) in H-C-C-13C)	99
3.3.2.3	Long-range Couplings ³+ ¹¹J(C.H)	99
3.3.3	C,H Couplings in Benzene Derivatives	99
3.4	C,C Coupling Constants and Chemical Structure	100
3.5	Correlations between C,H and H,H Coupling Constants	101
3.6	Coupling Mechanisms	102
3.6.1	The Electron-Nuclear Interaction	102
3.6.2	H,D Couplings	104
3.6.3	Relationship between the Coupling and the Lifetime of a Spin State	105
3.6.4	Couplings through Space ……………..	106
3.7	Couplings of “Other” Nuclides (Heteronuclear Couplings)	106
3.8	Bibliography for Chapter 3	109
4	Spectrum Analysis and Calculations	111
4.1	Introduction	111
4.2	Nomenclature	113
4.2.l	Systematic Notation for Spin Systems	113
4.2.2	Chemical and Magnetic Equivalence	114
4.3	Two-Spin Systems	116
4.3.1	The AX Spin System	116
4.3.2	The AB Spin System	118
4.4	Three-Spin Systems	120
4.4.1	The AX2, AK2, AB2 and A3 Spin Systems	120
4.4.2	The AMX and ABX Spin Systems	121
4.5	Four-Spin Systems	123
4.5.1	A2X2 and A2B2 Spin Systems	123
4.5.2	The AA’XX’ and AA’BB’ Spin Systems	124
4.6	Spectrum Simulation and Iteration	125
4.7	Analysis of 13C NMR Spectra	126
4.8	Bibliography for Chapter 4 .………….. .	127
5	Double Resonance Experiments ……. .	129
5.1	Introduction ………………………	129
5.2	Spin Decoupling in 1H NMR Spectroscopy ... .	130
5.2.l	Simplification of Spectra by Selective Spin Decoupling …………..	130
5.2.2	Suppression of a Solvent Signal …………	132
5.3	Spin Decoupling in 13C NMR Spectroscopy .. .	133
5.3.1	1H Broad-band Decoupling ……………	133
5.3.2	The Gated Decoupling Experiment ………	135
5.3.3	¹H Off-Resonance Decoupling ………… .	136
5.3.4	Selective Decoupling in 13C NMR Spectroscopy	137
5.4	Bibliograph)1 for Chapter 5 .………….. .	138
6	Assignment of ¹H and 13C Signals …….	139
6.1	Introduction …………………….. .	139
6.2	1H NMR Spectroscopy ……………… .	140
6.2.1	Defining the Problem ………………. .	140
6.2.2	Empirical Correlations for Predicting Chemical Shifts	141
6.2.2.1	Alkanes (Shoolery’s Rule) …………… .	141
6.2.2.2	Alkenes ……………………….. .	142
6.2.2.3	Benzene Derivatives……………….. .	143
6.2.3	Decoupling Experiments ……………..	145
6.2.4	Effects of Solvent and Temperature …….. .	145
6.2.5	Altering the Chemical Structure of the Sample	146
6.3	13C NMR Spectroscopy •	147
6.3.1	Defining the Problem ………………. .	147
6.3.2	Empirical Correlations for Predicting Approximate Chemical Shifts	148
6.3.2.l	Alkanes ……………………….. .	148
6.3.2.2	Alkenes ……………………….. .	151
6.3.2.3	Benzene Derivatives…………………	153
6.3.3	Decoupling Experiments ……………. .	154
6.3.4	T₁ Measurements …………………. .	154
6.3.5	Solvent and Temperature Effects and Shift Reagents	154
6.3.6	Chemical Changes to the Sample ………. .	154
6.4	Computer-aided Assignment of 13C NMR Spectra	156
6.4.1	Searching for Identical or Related Compounds	156
6.4.2	Spectrum Prediction . . . . . . . . . . . . . . . . . . . . .	151
6.5	Bibliography for Chapter 6. . . . . . . . . . . . . . . .	159
7	Relaxation . . . . . . . . . . . . . . . . . . . . . . . . . . .	16l
7.1	Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . .	I6 l
7.2	Spin-Lattice Relaxation of 13C Nuclei (T1).	162
7.2.1	Relaxation Mechanisms . . . . . . . . . . . . . . . . . .	162
7.2.2	Experimental Determination of T₁; the Inversion Recovery Experiment	164
7.2.3	Relationships between T, and Chemical Structure	168
7.2.3.1	Influence of Protons in CH, CH2 and CH3 Groups	168
7.2.3.2	Influence of Molecular Size . . . . . . . . . . . . . . .	169
7.2.3.3	Segmental Mobilities . . . . . . . . . . . . . . . . . . . .	170
7.2.3.4	Anisotropy of the Molecular Mobility. . . . . . . .	170
7.2.4	Suppression of the Water Signal . . . . . . . . . . . .	171
7.3	Spin-Spin Relaxation (T2) . . . . . . . . . . . . . . . .	171
7.3.1	Relaxation Mechanisms . . . . . . . . . . . . . . . . . .	17 I
7.3.2	Experimental Determination of T₂; the Spin-Echo Experiment	173
7.3.3	Line-widths of NMR Signals. . . . . . . . . . . . . . .	177
7.4	Bibliography for Chapter 7. . . . . . . . . . . . . . . .	178
8	One-Dimensional NMR Experiments using Complex Pulse Sequences . . . . . . . .	I 8I
8.1	Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . .	18J
8.2	Basic Techniques Using Pulse Sequences and Pulsed Field Gradients	182
8.2.1	The Effect of the Pulse on the Longitudinal Magnetization (Mz)	183
8.2.2	The Effect of the Pulse on the Transverse Magnetization Components(Mx•, My•)	184
8.2.3	The Effect of Pulsed Field Gradients on the Transverse Magnetization	187
8.3	The ]-Modulated Spin-Echo Experiment . . . . .	192
8.4	The Pulsed Gradient Spin-Echo Experiment . .	200
8.5	Signal Enhancement by Polarization Transfer. .	202
8.5.l	The SPI Experiment. . . . . . . . . . . . . . . . . . . . .	202
8.5.2	The INEPT Experiment. . . . . . . . . . . . . . . . . .	205
8.5.3	The Reverse INEPT Experiment with Proton Detection	213
8.6	The DEPT Experiment . . . . . . . . . . . . . . . . . .	218
8.7	The Selective TOCSY Experiment. . . . . . . . . .	223
8.8	The One-Dimensional INADEQUATE Experiment	225
8.9	Bibliography for Chapter 8. . . . . . . . . . . . . . . .	229
9	Two-Dimensional NMR Spectroscopy . . .	231
9.1	Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . .	23 I
9.2	The Two-Dimensional NMR Experiment. . . . .	232
9.2.1	Preparation, Evolution and Mixing, Data Acquisition	232
9.2.2	Graphical Representation. . . . . . . . . . . . . . . . .	236
9.3	Two-Dimensional ./-Resolved NMR Spectroscopy	237
9.3.1	Hctcronuclear Two-Dimensional}-Resolved NMR Spectroscopy	237
9.3.2	Homonuclear Two-Dimensional}-Resolved NMR Spectroscopy	241
9.4	Two-Dimensional Correlated NMR Spectroscopy	246
9.4.1	Two-Dimensional Heteronuclear (C.H)-Correlated NMR Spectroscopy (HETCOR or CH-COSY)	247
9.4.2	Two-Dimensional Homonuclear (H,H)-Correlated NMR Spectroscopy (H,H-COSY: Long-Range COSY)	255
9.4.3	Reverse Two-Dimensional Heteronuclear (H,C)-Correlated NMR Spectroscopy (HSQC; HMQC)	263
9.4.4	The Gradient-Selected (gs-)HMBC Experiment	268
9.4.5	The TOCSY Experiment…. . . . . . . . . . . . . .	273
9.4.6	Two-Dimensional Exchange NMR Spectroscopy: The Experiments NOESY ROESY and EXSY	276
9.5	The Two-Dimensional INADEQUATE Experiment	281
9.6	Summary of Chapters 8 and 9. . . . . . . . . . . . . .	286
9.7	Bibliography for Chapter 9. . . . . . . . . . . . . . . .	287
10	The Nuclear Overhauser Effect . . . . . . . . .	289
10.l	Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . .	289
10.2	Theoretical Background. . . . . . . . . . . . . . . . . .	290
10.2.l	The Two-Spin System. . . . . . . . . . . . . . . . . . . .	290
10.2.2	Enhancement Factors. . . . . . . . . . . . . . . . . . . .	293
10.2.3	Multi-Spin Systems	294
10.2.4	From the One-Dimensional to the Two-Dimensional Experiments, NOESY and ROESY	295
10.3	Experimental Aspects . . . . . . . . . . . . . . . . . . .	296
10.4	Applications. . . . . . . . . . . . . . . . . . . . . . . . . . .	298
10.5	Bibliography for Chapter 10. . . . . . . . . . . . . . .	303
11	Dynamic NMR Spectroscopy (DNMR) ..	30S
11.1	Introduction …………………….. .	305
11.2	Quantitative Calculations ……………. .	309
11.2.1	Complete Line-shape Analysis ………… .	309
1l.2.2	The Coalescence Temperature Tc and the Corresponding Rate Constant kc	311
11.2.3	Activation Parameters ……………… .	312
11.2.3.1	The Arrhenius Activation Energy £A ……. .	312
11.2.3.2	The Free Enthalpy of Activation t::,.G ……..	313
11.2.3.3	Estimating the Limits of Error ………….	314
11.2.4	Rate Constants in Reactions with Intermediate Stages	315
11.2.5	Intermolecular Exchange Processes . . . . . . . . .	3 16
11.3	Applications. . . . . . . . . . . . . . . . . . . . . . . . . . .	3 17
ll.3.1	Rotation about CC Single Bonds . . . . . . . . . . .	317
11.3.1.1	C(sp3)-C(sp3) Bonds. . . . . . . . . . . . . . . . . . . .	318
ll.3.1.2	C(sp2)-C(sp3) Bonds. . . . . . . . . . . . . . . . . . . .	3 I 8
11.3.1.3	C(sp2)-C(sp2) Bonds. . . . . . . . . . . . . . . . . . . .	319
11.3.2	Rotation about a Partial Double Bond . . . . . . .	319
ll.3.3	Inversion at Nitrogen and Phosphorus Atoms. .	321
11.3.4	Ring Inversion . . . . . . . . . . . . . . . . . . . . . . . . .	322
11.3.5	Valence Tautomerism. . . . . . . . . . . . . . . . . . . .	325
11.3.6	Keto-Enol Tautomerisrn. . . . . . . . . . . . . . . . . .	326
11.3.7	Intermolecular Proton Exchange . . . . . . . . . . .	327
ll.3.8	Reactions and Equilibration Processes . . . . . . .	329
11.4	Bibliography for Chapter 11. . . . . . . . . . . . . . .	332
12	Shift Reagents. . . . . . . . . . . . . . . . . . . . . . . .	335
12.1	Lanthanide Shift Reagents (LSRs) . . . . . . . . . .	335
12.1.1	Fundamentals. . . . . . . . . . . . . . . . . . . . . . . . . .	335
12.1.2	Applications and Quantitative Interpretation . .	337
12.2	Chiral Lanthanide Shift Reagents. . . . . . . . . . .	340
12.3	Chiral Solvents. . . . . . . . . . . . . . . . . . . . . . . . .	342
*U.4*	Bibliography for Chapter 12. . . . . . . . . . . . . . .	345
13	Macromolecules . . . . . . . . . . . . . . . . . . . . . .	347
13.1	Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . .	347
13.2	Synthetic Polymers. . . . . . . . . . . . . . . . . . . . . .	348
13.2.1	The Tacticity of Polymers. . . . . . . . . . . . . . . . .	348
13.2.2	Polymerization of Dienes . . . . . . . . . . . . . . . . .	35 I
13.2.3	Copolymers . . . . . . . . . . . . . . . . . . . . . . . . . . .	352
13.2.4	Solid-State NMR Spectroscopy of Polymers . . .	353
13.3	Biopolymers .……………………. .	355
13.3.J	Peptides and Proteins ………………..	356
13.3.1.l	Sequence Analysis ………………….	357
13.3.1.2	ThTehree-Dimensional Structure of Proteins ..	358
13.3.2	Polynucleotides ………………….. .	360
13.3.3	Oligosaccharides and Polysaccharides……. .	362
13.4	Bibliography for Chapter 13 .…………. .	366
14	NMR Spectroscopy in Biochemistry and Medicine	369
14.1	Introduction	369
14.2	Elucidating Reaction Pathways in Biochemistry	370
14.2.1	Syntheses using Singly 13C-Labeled Precursors	370
14.2.l.l	Low Levels of 13C Enrichment ………….	370
14.2.1.2	High Levels of 13C Enrichment	372
14.2.2	Syntheses using Doubly 13C-Labeled Precursors	373
14.3	High-Resolution in vivo NMR Spectroscopy	375
14.3.1	The Problem and its Solution	375
14.3.2	3 tp NMR Experiments	376
14.3.3	1 H and 13C NMR Experiments	379
14.4	Magnetic Resonance Tomography	380
14.4.1	Basic Principles and Experimental Considerations	380
14.4.2	Applications	386
14.4.2.1	Magnetic Resonance Tomography	386
14.4.2.2	Magnetic Resonance Spectroscopy, 1H MRS	390
14.5	Bibliography for Chapter 14	392
	Subject Index	395
	Index of Compounds	403

کتاب Basic One- and Two-Dimensional NMR Spectroscopy انگلیسی

دانلود pdf کتاب Basic One- and Two-Dimensional NMR Spectroscopy – Horst Friebolin

Fourth, Completely Revised and Updated Edition

Foreword

1-The Physical Basis of NMR Spectroscopy

Contents

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پکیج طلایی اصل سوالات عمومی از سال 86 تا 1402

پکیج جامع سوالات آموزش و پرورش حیطه اختصاصی

پکیج جامع سوالات آموزش و پرورش حیطه عمومی

کتاب گنجینه سوالات استخدامی آموزگار ابتدایی(3 حیطه کامل)

پکیج کامل آموزگار ابتدایی

کتاب PDF ترجمه مبانی طیف سنجی رزونانس مغناطیسی هسته یک و دو بعدی هورست فربولین

کتاب شیمی آلی پیشرفته جلد اول: ساختار و مکانیزم ها فرانسیس کری ترجمه PDF

کتاب ترجمه سنتز آلی پیشرفته PDF – فرانسیس کری، ریچارد ساندبرگ

ترجمه کتاب شیمی هتروسیکل گیل کریست PDF

کتاب نگرشی بر طیف سنجی پاویا ترجمه فارسی

نقد و بررسی‌ها

کتاب Basic One- and Two-Dimensional NMR Spectroscopy انگلیسی

دانلود pdf کتاب Basic One- and Two-Dimensional NMR Spectroscopy – Horst Friebolin

Fourth, Completely Revised and Updated Edition

Foreword

1-The Physical Basis of NMR Spectroscopy

Contents

آموزش ویدیویی باز کردن فایل های زیپ در گوشی های اندرویدی

محصولات مرتبط

نقد و بررسی‌ها

کتاب Basic One- and Two-Dimensional NMR Spectroscopy انگلیسی