Modern molecular photochemistry
During the last two decades the photochemistry of organic molecules has grown into an important and pervasive branch of organic chemistry. In "Modern Molecular Photochemistry", the author brings students up to date with the advances in this field - the development of the theory of photorea...
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Sausalito, Calif.
Univ. Science Books
1991
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| 020 | |a 0935702717 |9 0-935702-71-7 | ||
| 020 | |a 9780935702712 |9 978-0-935702-71-2 | ||
| 035 | |a (OCoLC)25361980 | ||
| 035 | |a (DE-599)BVBBV012867727 | ||
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| 100 | 1 | |a Turro, Nicholas J. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Modern molecular photochemistry |c Nicholas J. Turro |
| 264 | 1 | |a Sausalito, Calif. |b Univ. Science Books |c 1991 | |
| 300 | |a 628 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 520 | 3 | |a During the last two decades the photochemistry of organic molecules has grown into an important and pervasive branch of organic chemistry. In "Modern Molecular Photochemistry", the author brings students up to date with the advances in this field - the development of the theory of photoreactions, the utilization of photoreactions in synthetic sequences, and the advancement of powerful laser techniques to study the mechanisms of photoreactions. | |
| 650 | 4 | |a Chimie organique | |
| 650 | 4 | |a Photochimie | |
| 650 | 4 | |a Réactions chimiques | |
| 650 | 4 | |a Chemical reactions | |
| 650 | 4 | |a Chemistry, Organic | |
| 650 | 4 | |a Photochemistry | |
| 650 | 0 | 7 | |a Fotochemische Reaktion |0 (DE-588)4138378-3 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Organische Verbindungen |0 (DE-588)4043816-8 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Fotochemie |0 (DE-588)4045873-8 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Organische Chemie |0 (DE-588)4043793-0 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Fotochemische Reaktion |0 (DE-588)4138378-3 |D s |
| 689 | 0 | 1 | |a Organische Verbindungen |0 (DE-588)4043816-8 |D s |
| 689 | 0 | |5 DE-604 | |
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| 689 | 1 | 1 | |a Organische Verbindungen |0 (DE-588)4043816-8 |D s |
| 689 | 1 | |5 DE-604 | |
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| 689 | 2 | 1 | |a Organische Chemie |0 (DE-588)4043793-0 |D s |
| 689 | 2 | |8 1\p |5 DE-604 | |
| 856 | 4 | 2 | |m Digitalisierung UB Regensburg - ADAM Catalogue Enrichment |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008757032&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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Datensatz im Suchindex
| DE-BY-TUM_call_number | 0302/CHE 625f 1965 A 6357 |
|---|---|
| DE-BY-TUM_katkey | 1107251 |
| DE-BY-TUM_media_number | 040030191705 |
| _version_ | 1816711914099572736 |
| adam_text | Contents
Preface
111
1
Organic Photochemistry
—
An Overview
1
1.1
Molecular Photochemistry of Organic Molecules
1
1.2
Photochemical Reactions
2
1.3
The Electronic Excitation and Deexcitation of Organic Molecules
3
1.4
State Energy Diagrams: Electronic and Spin Isomers
4
1.5
Calibration Points for Molecular Dimensions and Molecular
Motions
6
1.6
Calibration Points for Molecular Energetics and Reaction
Dynamics
8
1.7
The Nuclear Geometry of Electronically Excited States
11
1.8
An Energy Surface Description of Molecular Photochemistry
12
1.9
Organic Photoreactions
14
1.10
Summary
15
References
16
2
Electronic
Orbitals,
Configurations, and States
17
2.1
Molecular Wavefunctions and Molecular Structure
17
2.2
The Born-Oppenheimer Approximation
17
2.3
The Spirit of the Use of Quantum Mechanical Operators
19
2.4
Atomic
Orbitals,
Molecular
Orbitals,
Electronic Configuration,
and Electronic States
20
2.5
The Ground State Configuration
21
CONTENTS
2.6
The Construction of Electronic States from Electronic
Configurations
23
2.7
Visualization of Electron Spin: A Simple
Vectorial
Model
24
2.8
Vectorial
Representation of Singlet and Triplet States Derived
from a Single Configuration
26
2.9
Electronic Energy
Différence
between Singlet and Triplet States
28
2.10
The Experimental Measurement of Orbital Energies: Photoelectron
Spectroscopy
32
2.11
Summary
36
References
37
3
Transitions Between States
—
Chemical Dynamics
38
3.1
Chemical Dynamics as Transitions between States
38
3.2
Classical Dynamics: Some Preliminary Comments
39
3.3
Quantum Dynamics: The Golden Rule for Transitions between
States
40
3.4
Transitions between States: Evaluation of Transition
Probabilities
41
3.5
Nuclear Motion; Vibronic States
43
3.6
Singlet-Triplet
Interconversions
46
References
51
4
Potential Energy Surfaces
52
4.1
Potential Energy Curves and Potential Energy Surfaces
52
4.2
Movement of a Classical Particle on a Surface
52
4.3
Potential Energy Curves and Surfaces for Visualization of
Molecular Behavior
56
4.4
The Quantum Mechanical Version of the Harmonic Oscillator
56
4.5
The Influence of Collisions and Vibrations on the Motion of
the Representative Point
63
4.6
Transitions between Potential-Energy Surfaces
64
4.7
The Franck-Condon Principle and Radiative Transitions:
A Classical Model
65
4.8
The Franck-Condon Principle and Radiationless Transitions:
Analogy to a Vibrating Spring
70
4.9
Visualization of Chemical versus Physical Mechanisms of
RadiationJess Transitions
72
4.10
Summary and Prospectus
74
References
75
CONTENTS
5
Radiative Transitions
—
The Absorption and
Emission of Light
76
5.1
Absorption and Emission Spectra of Organic Molecules
76
5.2
Typical Experimental Absorption and Emission Spectra of
Organic Molecules
77
5.3
The Nature of Light: Electromagnetic Waves and Oscillating
Electric
Dipo
les
78
5.4
Light as a Stream of
Partiales:
Photons
85
5.5
The Shape of Absorption and Emission Spectra
91
5.6
State Mixing: Breakdown of the Single Orbital Configuration
and Pure Multiplicity Approximations
96
5.7
Experimental Measurements of the Absorption and Emission of
Light: Molecular Electronic Spectroscopy
103
5.8
Spin-Orbit Coupling and Spm-Forbidden Radiative Transitions
117
5.9
Experimental Examples of Spm-Forbidden Radiative Transitions:
■Sq
—►
Τ
Absorption and Phosphorescence
121
5.10
Flash Spectroscopy
130
5.11
Excited State Structures and
Dipole
Moments
132
5.12
Radiative Transitions Involving more than One Molecule:
Absorption Complexes and Exciplexes
135
5.13
Delayed Fluorescence and Phosphorescence
146
5.14
Emission from Upper Excited Singlets and Triplets; The
Azulene Anomaly
148
References
148
6
Photophysical Radiationless Transitions
153
6.1
Photophysical Radiationless Transitions as a Form of Electronic
Relaxation
153
6.2
A Classical Interpretation of Radiationless Electronic Transitions
as Jumps between Surfaces
154
6.3
Wave Mechanical Interpretation of Radiationless Transitions
between States
155
6.4
Formulation of a Parameterized Model of Radiationless
Transitions
160
6.5
The Relationship of Rates and Efficiencies of Radiationless
Transitions to Molecular Structure
170
6.6
Factors that Influence the Rate of Vibrational Relaxation
174
6.7
The Evaluation of Rate Constants for Radiationless Processes
from Quantitative Emission Parameters
176
6.8
Internal Conversion (Sn
—
Ѕ1г
S
->
So)
180
6.9
Intersystem Crossing from
S y
to
Тг
185
6.10
Intersystem Crossing
(7
-*■
So)
188
CONTENTS
6.1
1 Perturbation of
Spin-FOrbidden
Radiationless Transitions
191
6.12
The Relationship between Photophysical
Radiationless
Transitions
and Photochemical Processes
194
References
195
Theoretical Organic Photochemistry
199
7.
1 A Qualitative Theory of Organic Photoreactions 1
99
7.2
The Principle of Maximum Positive Orbital Overlap
201
7.3
Orbital Interactions
202
7.4
Orbital and State Correlation Diagrams
206
7.5
The Construction of Electron Orbital and State Coordination
Diagrams for a Selected Reaction Coordinate
207
7.6
Typical State Correlation Diagrams for Concerted
Photochemical Pericyclic Reactions
209
7.7
State Correlation Diagrams for Photoreactions Involving
Diradical
Intermediates
215
7.8
Typical State Correlation Diagrams for Non-concerted
Photoreactions: Reactions Involving Intermediates
(Diradicals and
Zwitterions) 219
7.9
State Correlation Diagrams for
α
-Cleavage of Ketones
224
7.10
A Standard Set of Primary Photoreactions for
π,π*
and
/2,π*
States
228
7.11
Conclusion: Energy Surfaces as Reaction Graphs
230
References
231
8
Mechanistic Organic Photochemistry
232
8.1
Mechanisms
232
8.2
Use of Kmetic Feasibility
m
Quantitative Mechanistic Analyses
235
8.3
The Use of Structural Criteria and the Role of Reactive
Intermediates in Mechanistic Analysis
238
8.4
Rules for Proceeding from Rate Laws to Inferring Photochemical
Reaction Mechanisms
241
8.5
Rules for Proceeding from Efficiency Laws to Inferring
Photochemical Reaction Mechanisms
243
8.6
Experimental Methods for Determining Rate Constants of
Photoreactions
245
8.7
Experimental Examples of the Measurements of Photochemical
Rate Constants
248
8.8
Reactive Intermediates: Experimental Detection and
Characterization
254
8.9
Experimental Tests for Reactive Intermediates
255
CONTENTS
8.10
Experimental
Tests
for the Involvement of Radicals and
Diradicals
264
8.11
Magnetic Resonance Methods for Detecting Radicals, Radical
Pairs, and Diradicals
266
8.12
Chemically Induced Nuclear Polarization and the Experimental
Detection of Radical Pairs
273
8.13
Chemical Spectroscopy
:
The Use of Photochemical Reactions to
Measure Excited State Energetics and Dynamics
288
8.14
Some Archetype State-Energy Diagrams
291
References
294
9
Energy Transfer
296
9.1
An Energy-Surface Description of Electronic Energy Transfer
and Energy Degradation
296
9.2
The Trivial or Radiative Mechanism for Electronic Energy
Transfer: The Spectral Overlap Integral
298
9.3
Theory of Radiationless Energy Transfer
:
A General
Formulation
299
9.4
Visualization of Energy Transfer by Coulombic Interactions:
A Transmitter-Antenna Mechanism
301
9.5
Energy Transfer by Electron Exchange: An Overlap or
Collision Mechanism
305
9.6
The Role of Energetics in Energy Transfer Mechanisms
309
9.7
The Role of Molecular Diffusion in Energy Transfer Processes
in Fluid Solution; Diffusion Controlled Quenching
311
9.8
Distance-Ttme Relationships for Diffusion
316
9.9
Energy Transfer in the Absence of Diffusion
:
The Perrin
Formulation
317
9.10
Comparison of the Theoretical Distance Dependencies of
Energy Transfer Rates and Efficiencies
319
9.11
Experimental Examples of Singlet-Singlet Energy Transfer
321
9.12
Triplet-Triplet Energy Transfer
328
9.13
Triplet-Singlet Energy Transfer in Fluid Solution
338
9.14
Singlet-Triplet Energy Transfer
339
9.15
Excitation Transfer between Conjugated Chromophores
340
9.16
Multiphoton Energy Transfer Processes; Triplet-Triplet
Annihilation; Delayed
Photoluminescence
343
9.17
Energy Transfer from Upper Excited States
344
9.18
Non verticai
Energy Transfer
346
9.19
Reversible Energy Transfer
349
9.20
Photosensitization and Quenching in Organic Photochemistry
351
9.21
Quenching by Molecular Oxygen
354
9.22
Energy Hopping or Energy Migration
354
References
358
CONTENTS
10
Photoaddition and Photosubstitution
Reactions
362
I O.I Classification of Photochemical Additions and Substitution
Reactions
362
10.2
Photoreduction of Carbonyl Compounds and Ethylenes: Linear
Addition Initiated by Hydrogen Abstraction Reactions
363
10.3
The Use of Radical Models for Hydrogen Abstraction from
η,π*
and
π,π*
States
364
10.4
Theoretical Analysis of Hydrogen and Electron Abstraction
Reactions of Ketones
367
10.5
Synthetic Applications of Photochemical Hydrogen Abstraction
Reactions
368
10.6
Mechanistic Analysis of the Photoreduction of Ketones
372
10.7
Quantitative Analysis of the Efficiency of Photoreduction
377
10.8
Experimental Examples of the Competition between Hydrogen
Abstraction and Electron Abstraction
383
10.9
Intramolecular Hydrogen Abstraction: The Type II Family of
Reactions
386
10.10
Photochemical Hydrogen and Electron Abstraction of Carbonyl
Derivatives and Unsaturated Nitrogen Compounds
393
10.11
Addition Reactions of Acyclic Ethylenes
395
10.12
Photochemical Aromatic Substitution
404
10.13
Summary
408
References
409
11
Cycloaddition
Reactions
414
11.
1 Classification of Cycloaddition Reactions
414
11.2
Photocycloadditions via Intermediates: Diradicals,
Zwitterions,
and Exciplexes
417
11.3 [2 + 2]
Photocycloaddition Reactions of Carbonyl Compounds
432
11.4
Photocycloadditions of Benzene
452
11.5
Photocycloaddition Reactions of Conjugated Enones
458
11.6
Photocycloadditions Involving Unsaturated Nitrogen
Compounds and Thioketones
465
11.7
Summary
467
References
467
12
Isomerizations and Rearrangements
473
12.1
Classification of Photochemical Rearrangements
473
12.2
Cis-trans Isomerization of Unsaturated Compounds
473
12.3
Skeletal and Positional Photoisomerizations
:
Sigmatropic
Rearrangements
482
13
.1
13
.2
13
.3
13
.4
13
.5
13.6
13
.7
CONTENTS
12.4
Electrocyclic Reactions
493
12.5
Intramolecular
Cycloadditions
of Conjugated Hydrocarbons
505
12.6
Electrocyclic
Reactions and Intramolecular
Cycloadditions
of Heteroatomic Conjugated Systems
508
12.7
Sigmatropic Isomenzations of /^y-Unsaturated Enones
519
12.8
Summary
520
References
520
13
Photofragmentation
Reactions
526
Photofragmentations
and Photoelimmations
526
Homolyüc
α
-Cleavage of Ketones; An Alkoxy
Radicai
Model
528
Sigmatropic Rearrangements of
β,
y-Unsaturated Ketones
Initiated by
α
-Cleavage
539
Photoelimination Reactions of
Azo
Compounds
544
Photoelimination of Nitrogen from Diazocompounds, Azides,
and Related Compounds
550
Photochemical Cleavage of Small Rings
557
Miscellaneous
α
-Cleavage Reactions of Peroxides, Halides,
and Nitrites; The Barton Reaction
568
13.8
Summary
571
References
572
14
Singlet Oxygen and Chemiluminescent
Organic Reactions
579
14.1
A Conceptual Link between Photoreactions and
Chemiluminescent Organic Reactions
579
14.2
Molecular Oxygen: Ground State
(3Σ)
and Excited Singlet
States
0Δ
and
ΧΣ)
583
14.3
Chemiluminescence of
1
,2-Dioxetanes and Endo-Peroxides
594
14.4
Applications of Chemiexcitation to Photochemicai Problems
605
14.5
Adiabatic Photoreactions
:
Examples of Chemiluminescent
Photoreactions
608
14.6
Red Light to Blue Light Experiments and Uphill
Photosensitization
609
14.7
Interplay of Organic Photochemistry and Chemiluminescent
Organic Reactions
611
References
6Π
Epilogue
615
Index
616
|
| any_adam_object | 1 |
| author | Turro, Nicholas J. |
| author_facet | Turro, Nicholas J. |
| author_role | aut |
| author_sort | Turro, Nicholas J. |
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| building | Verbundindex |
| bvnumber | BV012867727 |
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| classification_tum | CHE 606f CHE 625f CHE 189f |
| ctrlnum | (OCoLC)25361980 (DE-599)BVBBV012867727 |
| dewey-full | 541.35 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 541 - Physical chemistry |
| dewey-raw | 541.35 |
| dewey-search | 541.35 |
| dewey-sort | 3541.35 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Physik Chemie |
| format | Book |
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| id | DE-604.BV012867727 |
| illustrated | Illustrated |
| indexdate | 2024-11-25T17:16:24Z |
| institution | BVB |
| isbn | 0935702717 9780935702712 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-008757032 |
| oclc_num | 25361980 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-20 DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-703 DE-11 |
| owner_facet | DE-91G DE-BY-TUM DE-20 DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-703 DE-11 |
| physical | 628 S. Ill., graph. Darst. |
| publishDate | 1991 |
| publishDateSearch | 1991 |
| publishDateSort | 1991 |
| publisher | Univ. Science Books |
| record_format | marc |
| spellingShingle | Turro, Nicholas J. Modern molecular photochemistry Chimie organique Photochimie Réactions chimiques Chemical reactions Chemistry, Organic Photochemistry Fotochemische Reaktion (DE-588)4138378-3 gnd Organische Verbindungen (DE-588)4043816-8 gnd Fotochemie (DE-588)4045873-8 gnd Organische Chemie (DE-588)4043793-0 gnd |
| subject_GND | (DE-588)4138378-3 (DE-588)4043816-8 (DE-588)4045873-8 (DE-588)4043793-0 |
| title | Modern molecular photochemistry |
| title_auth | Modern molecular photochemistry |
| title_exact_search | Modern molecular photochemistry |
| title_full | Modern molecular photochemistry Nicholas J. Turro |
| title_fullStr | Modern molecular photochemistry Nicholas J. Turro |
| title_full_unstemmed | Modern molecular photochemistry Nicholas J. Turro |
| title_short | Modern molecular photochemistry |
| title_sort | modern molecular photochemistry |
| topic | Chimie organique Photochimie Réactions chimiques Chemical reactions Chemistry, Organic Photochemistry Fotochemische Reaktion (DE-588)4138378-3 gnd Organische Verbindungen (DE-588)4043816-8 gnd Fotochemie (DE-588)4045873-8 gnd Organische Chemie (DE-588)4043793-0 gnd |
| topic_facet | Chimie organique Photochimie Réactions chimiques Chemical reactions Chemistry, Organic Photochemistry Fotochemische Reaktion Organische Verbindungen Fotochemie Organische Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008757032&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT turronicholasj modernmolecularphotochemistry |