Molecular structure: understanding steric and electronic effects from molecular mechanics
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Hoboken, NJ
Wiley
2010
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis Klappentext |
| Beschreibung: | XIX, 333 S. Ill., graph. Darst. |
| ISBN: | 9780470195574 |
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| 245 | 1 | 0 | |a Molecular structure |b understanding steric and electronic effects from molecular mechanics |c Norman L. Allinger |
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Datensatz im Suchindex
| _version_ | 1804143219009650688 |
|---|---|
| adam_text | CONTENTS
Foreword
xi
Preface
xv
Acknowledgments
xix
1
INTRODUCTION
1
What, Exactly, is a Molecular Structure?
3
References
6
2
EXPERIMENTAL MOLECULAR STRUCTURES
7
Electron Diffraction
7
Microwave Spectroscopy
10
Х
-Ray Crystallography
11
The Phase Problem
12
Rigid-Body Motion
14
Molecular Mechanics in Crystallography
16
Neutron Diffraction
17
Nuclear Magnetic Resonance Spectra
19
Bond Lengths Depend on Method Used to Determine Them
20
References
25
3
MOLECULAR STRUCTURES BY COMPUTATIONAL METHODS
28
A Brief History of Computers
28
Computational Methods
33
Semiempirical Quantum Mechanical Methods
34
Self-Consistent Field Method
35
Ab Initio
Methods
37
Density Functional Theory
41
Molecular Mechanics
42
References
47
VI
CONTENTS
MOLECULAR
MECHANICS OF
ALK AN ES
51
Potential Energy Surface
51
Force Constant Matrix
57
Diagonal Part
57
Vibrational Spectra
58
Off-Diagonal Part
63
Stretch-Bend Effect
65
Urey-Bradley Force Field
66
van
der Waals
Forces
66
Dr. Miller s Nuclear Explosion
73
van
der Waals
Interactions between Nonidentical Atoms
74
Congested Molecules
75
Tetracyclododecane
76
Vibrational Motions of Compressed Hydrogens
80
Other Very Short
H
-Н
Distances
81
Alkanes Summary
84
Extension of The Alkane Force Field
85
Alkenes
88
Functional Groups in Molecular Mechanics
89
References
90
CONJUGATED SYSTEMS
92
Introduction
92
Structures of Conjugated Hydrocarbons
98
in-[3410][7]Metacyclophane
102
Aromatic Compounds
104
Simple Benzenoid Compounds
105
Corannulene
108
CorFullerene
109
Aromaticky
112
Cyclooctatetraene
115
[lOHlójAnnulenes
116
[îejAnnulene
116
Triquinacene (Homoaromaticity)
118
Electronic Spectra
122
Structures of Conjugated Heterocycles
124
Porphyrins
127
References
129
CONTENTS
VU
6
EFFECTS IN ORGANIC CHEMISTRY
134
Electronegativity Effect
137
Electronegativity Effect on Bond Lengths
138
Electronegativity Effect on Bond Angles
143
C
-Н
Bond Length versus Vibrational Frequency
144
Hyperconjugation
147
Baker-Nathan Effect
151
References
160
7
MORE EFFECTS —NEGATIVE HYPERCONJUGATION
162
Bohlmann
Effect
163
Anomeric Effect
167
Dimethoxymethane
169
Energetic Effects
169
Structural Effects
170
Angle Effects
173
2-Methoxytetrahydropyran
173
α
-Halo
Ketone
Effect
177
Molecular Mechanics Model
182
Energetics
185
Summary
186
References
186
8
ADDITIONAL STEREOCHEMICAL EFFECTS IN CARBOHYDRATES
189
Glucose
189
Gauche Effect
193
Polyoxyethylene
(POE) 195
Delta-Two Effect
197
Glucose Diastereomers
200
Cellobiose Analog
201
External Anomeric
Torsionai
Effect
204
References
210
9
LEWIS BONDS
212
Hydrogen Bonds
212
Quantum Mechanical Description of a Hydrogen Bond
215
Hydrogen Bonding Models in Molecular Mechanics
218
VIII
10
11
CONTENTS
Hydrogen Fluoride Dimer
221
Water Dimer
222
Methanol
Dimer
223
Ethylene
Glycol
223
Other Lewis Bonds
227
Amine-Carbonyl Interactions
228
References
237
CRYSTAL STRUCTURE CALCULATIONS
239
Crystalline Phase
240
Anticipation of Unit Cell
241
A Priori Calculations of Crystal Structures
241
Molecular Mechanics Applications to Crystals
242
Comparison of
Х
-Ray Crystal Structure with Calculated
Structures
242
Benzene Crystal
243
Biphenyl
246
Ditrityl Ether
247
More of the [18]Annulene Story
249
References
254
HEATS OF FORMATION
257
Benson s Method
258
Statistical Mechanics
261
Heats of Formation of Alkanes from Molecular Mechanics
265
Tim Clark Story
269
Thermodynamic Properties of Alkanes
273
Heats of Formation from Quantum Mechanics: Alkanes
274
Strain Energy
282
Ring Strain Energy
285
Dodecahedrane
287
Heats of Formation of Unsaturated Hydrocarbons
291
[18]Annulene, Aromaticity
294
Fullerene
295
Heats of Formation of Functionalized Molecules
296
References
297
Concluding Remarks
301
CONTENTS
ІХ
Appendix
302
Introduction
302
Jargon
302
Basis Set Superposition Error
303
Carbohydrate Conformational Nomenclature
304
Conformational Search Routine
305
Driver Routine
308
Molecular Mechanics Programs
311
Nuclear Explosion Preventer
ЗІЗ
Quantum Chemistry Progam Exchange
313
Ring Counting
315
Stereographic
Projections
317
References
319
Index
321
Until recently, the study of organic molecules has traveled down two disparate intel¬
lectual paths
—
the experimental, or physical, method and the computational, or
theoretical, method. Working somewhat independently of each other, these disciplines
have guided research for decades, but they are now being combined efficiently into
one unified strategy.
Molecular Structure delivers the essential fundamentals on both the experimental and
computational methods, then goes further to show how these approaches can join
forces to produce more effective analysis of the structure and properties of organic
compounds by:
•
Looking at experimental structures: electron, neutron, X-ray diffraction, and
microwave spectroscopy as well as computational structures:
ab initio,
semi-empirical molecular orbital, and molecular mechanics calculations
•
Discussing various electronic effects, particularly stereoelectronic effects, including
hyperconjugation, negative hyperconjugation, the
Bohlmann
and anomeric effects,
and how and why these cause changes in structures and properties of molecules
•
Illustrating complex carbohydrate effects such as the gauche effect, the delta-two
effect, and the external anomeric
torsionai
effect
•
Covering hydrogen bonding, the CH bond, and how energies, especially heats of
formation, can be affected
•
Using molecular mechanics to tie all of these things together in the familiar
language of the organic chemist, valence bond pictures
Authored by a founding father of computational chemistry, Molecular Structure broad¬
ens the scope of the subject by serving as a pioneering guide for workers in the fields
of organic, biological, and computational chemistry, as they explore new possibilities
to advance their discoveries. This work will also be of interest to many of those in
tangential or dependent fields, including medicinal and pharmaceutical chemistry
and pharmacology.
Norman L. Aijjngkr received his BS from the University of California, Berkeley, in
1951
and his PhD from the University of California, Los Angeles, in
1954.
He was on
the faculty at Wayne State University before coming to the University of Georgia as
Research Professor in
1969.
He is known for his use of computational chemistry, espe¬
cially molecular mechanics, to solve a variety of chemical problems. He is the senior
author of the MM2, MM3, and MM4 molecular mechanics software packages.
|
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| discipline | Chemie / Pharmazie |
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| spelling | Allinger, Norman L. 1928-2020 Verfasser (DE-588)1030239762 aut Molecular structure understanding steric and electronic effects from molecular mechanics Norman L. Allinger Hoboken, NJ Wiley 2010 XIX, 333 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Molecular structure Physical organic chemistry Molekülstruktur (DE-588)4170383-2 gnd rswk-swf Computational chemistry (DE-588)4290091-8 gnd rswk-swf Organische Chemie (DE-588)4043793-0 gnd rswk-swf Molekülstruktur (DE-588)4170383-2 s Computational chemistry (DE-588)4290091-8 s Organische Chemie (DE-588)4043793-0 s DE-604 Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020532938&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020532938&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Allinger, Norman L. 1928-2020 Molecular structure understanding steric and electronic effects from molecular mechanics Molecular structure Physical organic chemistry Molekülstruktur (DE-588)4170383-2 gnd Computational chemistry (DE-588)4290091-8 gnd Organische Chemie (DE-588)4043793-0 gnd |
| subject_GND | (DE-588)4170383-2 (DE-588)4290091-8 (DE-588)4043793-0 |
| title | Molecular structure understanding steric and electronic effects from molecular mechanics |
| title_auth | Molecular structure understanding steric and electronic effects from molecular mechanics |
| title_exact_search | Molecular structure understanding steric and electronic effects from molecular mechanics |
| title_full | Molecular structure understanding steric and electronic effects from molecular mechanics Norman L. Allinger |
| title_fullStr | Molecular structure understanding steric and electronic effects from molecular mechanics Norman L. Allinger |
| title_full_unstemmed | Molecular structure understanding steric and electronic effects from molecular mechanics Norman L. Allinger |
| title_short | Molecular structure |
| title_sort | molecular structure understanding steric and electronic effects from molecular mechanics |
| title_sub | understanding steric and electronic effects from molecular mechanics |
| topic | Molecular structure Physical organic chemistry Molekülstruktur (DE-588)4170383-2 gnd Computational chemistry (DE-588)4290091-8 gnd Organische Chemie (DE-588)4043793-0 gnd |
| topic_facet | Molecular structure Physical organic chemistry Molekülstruktur Computational chemistry Organische Chemie |
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