Greenberg / Liebman / Wasserman Strained Organic Molecules

Organic Chemistry: A Series of Monographs, Vol. 38
1. Auflage 2013
ISBN: 978-1-4832-1795-6
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, 422 Seiten, Web PDF

Strained Organic Molecule, Volume 38 considers the vast field of strained organic molecules. The book discusses energy and entropy; cyclopropane and cyclobutane; and unique strained groupings or building blocks. The text also describes the aesthetics, rearrangements, and topology of polycycles; kinetic and thermodynamic stability; and tetrahedral tetracoordinate carbon. The inverted tetrahedra, propellanes, buttaflanes, and paddlanes; planar methane and its derivatives; and five- and six-coordinaste carbon are also considered. Chemists will find the book invaluable.

Dr. Arthur Greenberg is a Professor of Chemistry at the University of New Hampshire. His research interests include physical organic chemistry and environmental organic chemistry. Emphases include strained organic molecules such as bridgehead bicyclic lactams, having twisted amide linkages, and epoxyoxepins of possible relevance to benzene metabolism. Interests include airborne carcinogens such as polycyclic aromatic hydrocarbons (PAH) and their derivatives.

Autoren/Hrsg.

Greenberg, Arthur

Liebman, Joel F.

Wasserman, Harry H.

Inhaltsverzeichnis

1;Front
Cover;1
2;Strained Organic Molecules;4
3;Copyright Page;5
4;Table of Contents;6
5;Preface;10
6;CHAPTER 1. Energy and Entropy;16
6.1;1.A
Reference States and Reference Books;16
6.2;1.B
Origin of Molecular Strain;28
6.3;1.C
Thermodynamics and Symmetry;36
6.4;1.D
Potential Energy Curves and Zero-Point Energy;39
7;CHAPTER 2. Cyclopropane and Cyclobutane;44
7.1;2.A Conceptual Models for the Bonding in Cyclopropane;44
7.2;2.B Selected Reactions of Cyclopropanes;61
7.3;2.C Cyclobutane;70
8;CHAPTER 3. Unique Strained Groupings or Building Blocks;79
8.1;3.A Cycloalkanes;80
8.2;3.B Bicyclic, Spirocyclic, and Bridged Hydrocarbons;85
8.3;3.C Tetrahedrane;100
8.4;3.D Strained Alkenes: Molecules Lacking Torsional Strain;105
8.5;3.E Torsionally Distorted
p Bonds;123
8.6;3.F "Bredt Compounds9' and Cyclic
Allenes;141
8.7;3.G Cycloalkynes, Benzyne, and Cyclocumulenes;148
8.8;3.H Distorted Aromatic Rings;154
9;CHAPTER 4. Polycycles: Aesthetics, Rearrangements, and Topology;193
9.1;4.A Adamantanes and Higher Homologues;193
9.2;4.B Iceane;212
9.3;4.C Miscellaneous Acid-Catalyzed Rearrangements;214
9.4;4.D Strained Molecules of Formula (CH)n;218
9.5;4.E Additional Polycyclic Molecules;230
9.6;4.F Molecular Topology;235
10;CHAPTER 5. Kinetic and
Thermodynamic Stability;240
10.1;5.A Introduction;240
10.2;5.B Orbital Symmetry and Stabilities of Benzene Valence Isomers;243
10.3;5.C Transition Metals and Strained Carbocyclic Molecules;260
10.4;5.D Strained Heterocyclic Molecules;292
10.5;5.E Substituted Derivatives of Strained Molecules;340
11;CHAPTER 6. A Potpourri of Pathologies;357
11.1;6.A When is Tetracoordinate Carbon Tetrahedral?;357
11.2;6.B Inverted Tetrahedra, Propellanes, Buttaflanes, and Paddlanes;358
11.3;6.C Planar Methane and Its Derivatives;384
11.4;6.D Five- and Six-Coordinate Carbon;390
12;Addendum;401
13;Index;407
14;ORGANIC CHEMISTRY;422