Stereochemistry. Basic Concepts and Applications

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6. [Stereochemistry] | Organic Chemistry |

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Welcome back. University Chemistry University Chemistry. RichHTML 0. PDF PC Knowledge 0. Organic Chemistry , 6th ed. Organic Chemistry , 11th ed. Related Articles University Chemistry, , 34 4 : University Chemistry, , 33 7 : Past and Present of Nimodipine as Hypotensor [J]. Th e interaction between conformational analysis and the earlier studie s b y Hughe s and Ingold o f the mechanism o f nucleophilic aliphatic substitution reaction s wa s directly responsible for many o f the important development s which hav e taken place subsequently in physical organic chemistry.

Th e examination o f the stereochemistry o f organic reaction s is now a recognize d approach in the investigation o f the mechanism o f organic reactions.

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The principle s o f conformational analysis , in association with an apprecia- tion o f the stereo-electronic features o f reaction mechanisms , have ha d a profoun d influence on the design o f new synthetic method s which are either stereoselective or stereospecific. Efficient stereocontrol in the total synthesis o f compound s with complex acycli c or cycli c chiral molecule s is now a ix recognized attribute o f modern organic chemistry.

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Furthermore , much progres s has been made recently in developing a well-based understanding o f the phenomenon o f asymmetric induction. It was precisely the confidence which organic chemists had acquired in proposing statisfactory rationaliza- tions o f stereospecific reaction s which led t o the recognition that it was not possible , using current knowledge in the s, t o account for the remark- able stereospecificity o f many thermal and photochemical concerted peri- cyclic transformations. Thi s challenge was met b y Woodwar d and Hoffmann b y their ability t o correlate a colossal array o f chemical information on the basis o f the simple concept that concerted pericyclic reaction s can procee d favourably i f orbital symmetry is conserved without the imposition o f unacceptable stereochemical constraints.

The structure o f molecule s can b e considered at three level s — constitu- tion , configuration , and conformation. Following the first direct determina- tion o f an absolute configuration b y Bijvoet , tremendou s progres s has been mad e in the determination o f the absolute configurations o f many chiral organic molecules , either b y direct or b y correlative methods.

Th e study o f the absolute configuration o f many natural product s has le d t o great interest in the stereochemistry o f biosynthetic processes. There have also been exciting and important development s in the definition o f the sterochemistry o f enzyme action. It can b e truly claimed that stereochem- istry now provide s an important link between chemistry , bio-organic chemistry, biochemistry , and molecular biology. A detailed understanding o f drug-receptor interaction cannot b e far away and one can look forward t o the synthesis o f drug s whose molecular designs are based upon accurate stereochemical detail.

In recent year s there have been major changes in stereochemical concept s and nomenclature. Th e need t o specify molecular chirality generated the excellent proposal s o f Cahn, Ingold , and Prelog and the ultimate creation o f a new language , which has enabled stereochemist s t o describe molecules and intermolecular reaction s in precise and unambiguou s terms. Subsequently the concept o f stereochemical nonequivalence heterotopi - city o f apparently identical ligand s has acquired a fundamental importance in many enzymatic reaction s and much o f the mystery associated with the stereospecificity o f biological processe s has been removed.

Similar advance s have occurred in organic chemistry since Prelog advocate d the de - scription o f stereochemical entities in topological terms. Thi s approach has led t o the fascinating development o f chemical topology. The current availability o f modern instrumentation has also had an important influence on the growth o f stereochemistry. Knowledg e o f th e x geometry o f molecule s in the solid state is now rapidly obtainable using automated X-ray methods. Th e study o f the temperature dependence o f nuclear magnetic resonance spectra provide s quantitative information on the conformational behaviour o f molecule s in solution.

Introduction to chirality - Stereochemistry - Organic chemistry - Khan Academy

From this survey it will b e apparent that the science o f stereochemistry , created b y Pasteur , van't Hof f , and L e Bel well over a century ago , continue s t o provid e an exciting and rewarding area o f ex - perimental enquiry. Department o f Chemistry W. Ollis University o f Sheffield England x i Preface It is perhap s somewhat unfortunate that w e use conventional symbol s t o identify molecule s an d because these are presented on paper in on e plane , our chemical thinking tend s t o develop in tw o dimensions.

W e find ourselve s in this situation because the macroscopi c appearance o f chemical com - pound s colour , state , etc. Thi s may explain that although there is n o such discipline as for exampl e stereo-biology or stereo-physics , it is both necessary and expedient t o discuss separately th e three-dimen- sional aspect s o f chemistry.

Although not unimportant contributions , both ol d an d recent , hav e com e from th e field o f metal complexes , it cannot b e denie d that th e overwhelm - ing majority o f stereochemical investigation s are associated with organic chemistry. In view o f this , almost all the important concept s o f stereochem- istry can b e demonstrated b y example s taken from organic chemistry.

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Even though , apart from a few pages , thi s boo k deals with th e stereochem- istry o f organic compounds , thi s is not reflected in th e title since in our opinion the conclusion s can b e applied almost directly t o other fields o f chemistry. For many decade s thereafter almost everything that wa s achieved in stereochemistry can b e regarded as the experimental verifica- tion o f their theory.

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Thi s can b e regarded as th e secon d era o f stereochemistry. Th e third on e is now taking shape an d it is characterized b y an integration o f stereochemistry with almost every field o f chemistry. Stereochemistry has ceased t o b e a separate field o f investigation : stereochemical thinking has becom e indispensable in both preparative and mechanistic organic chemistry , xiii in biochemistry , in inorganic and polymer chemistry.

Stereochemistry: Basic Concepts and Applications

Thi s boo k wishes t o serve the advancement o f the third era b y introducing the basic principles and concepts , both ol d and modern , o f stereochemistry and b y demonstrating their application b y means o f a few examples. Thi s is implemented b y a discussion o f the most important method s used in stereochemical research. A restatement o f the principles o f stereochemistry is both timely and possible since after th e explosive development o f concept s and methodology in the s and early s, the pac e has now slowed down. Th e recent past has been marked on the one hand b y a spectacular development in the application o f instrumental technique s — most importantly o f nuclear magnetic resonance and chiroptical method s — and on the other b y the establishment o f a consistent system o f concept s and notation s based on symmetry principles and mathematical group theory.

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