3 edition of anomeric effect and related stereoelectronic effects at oxygen found in the catalog.
anomeric effect and related stereoelectronic effects at oxygen
Anthony J. Kirby
Includes bibliographical references and index.
|Statement||Anthony J. Kirby.|
|Series||Reactivity and structure ;, v. 15|
|LC Classifications||QD471 .K5 1983|
|The Physical Object|
|Pagination||149 p. :|
|Number of Pages||149|
|LC Control Number||82005889|
Stereoelectronic Effects illustrates the utility of stereoelectronic concepts using structure and reactivity of organic molecules Reverse anomeric effect “Anomeric effects without lone pairs”: beyond the n→σ* interactions "This book is highly recommended to every chemist and particularly to every student to. oxygen, nitrogen, sulfur, and other heteroatoms are well documented in the scientific literature. Arguably, the best documented and the most intensively studied of such effects is the anomeric effect,19 The anomeric effect was originally defined as the preference for an electronegative substituent positioned next to an oxygen.
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The Anomeric Effect and Related Stereoelectronic Effects at Oxygen. Authors: Kirby, A. Free PreviewBrand: Springer-Verlag Berlin Heidelberg. : The Anomeric Effect and Related Stereoelectronic Effects at Oxygen (Reactivity and Structure: Concepts in Organic Chemistry) (): Anthony John Kirby, Dennis Young: BooksCited by: : Anomeric Effect and Related Stereoelectronic Effects at Oxygen (Reactivity & Structure) (): Kirby, Anthony John: BooksAuthor: Anthony John Kirby.
The Anomeric Effect and Related Stereoelectronic Effects at Oxygen. Authors (view affiliations) Anthony John Kirby; Search within book. Front Matter. Pages i-viii. PDF. Anthony John Kirby.
Pages Stereoelectronic Effects on Reactivity: The Kinetic Anomeric Effect. Anthony John Kirby. Pages Appendix. Anthony John Kirby. Anomeric effect and related stereoelectronic effects at oxygen. Berlin ; New York: Springer-Verlag, (OCoLC) Material Type: Internet resource: Document Type: Book, Internet Resource: All Authors / Contributors: Anthony J Kirby.
ISBN: OCLC Number: Description: 1 online resource: Contents: A. Stereoelectronic Effects on Structure Introduction The Anomeric Effect The Reverse Anomeric Effect The Exo-Anomeric Effect The Generalised Anomeric Effect The Gauche Effect Electronic Basis of the Effects In: The Anomeric Effect anomeric effect and related stereoelectronic effects at oxygen book Related Stereoelectronic Effects at Oxygen.
Reactivity and Structure Concepts in Organic Chemistry, vol Springer, Berlin, HeidelbergCited by: 2. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen Reactivity and Structure: Concepts in Organic Chemistry: : Anthony John Kirby, Dennis Young: Libros en Format: Tapa blanda.
In the tetrahydropyran ring, Y= oxygen, which is a heteroatom, so the anomeric effect contributes and stabilizes the observed substituent position. In both cases, X= OMe. The anomeric effect is most often observed when Y= oxygen, but can also be seen with other lone pair bearing heteroatoms in the ring, such as nitrogen, sulfur, and phosphorus.
. The (normal) anomeric effect is the preference of an electronegative substituent for the axial position on a tetrahydrofuran (Juaristi & Cuevas, ; Kirby, ; Thatcher, ; Thibaudeau & Chattopadhyaya, ). This book provides a comprehensive review of the structural, conformational, and chemical manifestations of the anomeric effect.
In order to present a cogent discussion of this most fundamental and relevant phenomenon, three chapters examine our present understanding of the origin of this conformational effect, based upon a wealth of theoretical and physical data.
Stereoelectronic Effects illustrates the utility of stereoelectronic concepts using structure and reactivity of organic molecules. This advanced textbook provides an up-to-date overview of the field, starting from the fundamental principles and presenting a large selection of modern examples of stereoelectronic effects in organic reactivity.
In chemistry, primarily organic and computational chemistry, a stereoelectronic effect is an effect on molecular geometry, reactivity, or physical properties due to spatial relationships in the molecules' electronic structure, in particular the interaction between atomic and/or molecular orbitals.
This effect is now considered to be a special case of a general preference (the generalized anomeric effect) for gauche conformations about the bond CðY in the system XðCðYðC where X and Y are heteroatoms having nonbonding electron pairs, commonly at least one of which is nitrogen, oxygen, sulfur or Size: 1MB.
In furanoses, a high selectivity of the axial orientation of substituents at the anomeric center is established statistically through crystallographic data studies of anomeric substructures and related hydrocarbons.
This fact constitutes conclusive evidence of non equivalence of the endo oxygen lone pairs (O = sp 2).Cited by: This chapter also introduces a number of classic stereoelectronic effects on reactivity such as the gauche effect, the anomeric and homoanomeric effects, the β-silicon and β-tin effects etc.
The remainder of the book is devoted to new areas of development in the topic-such as differentiation of the endo and exo anomeric interactions, specific analysis of the enthalpic component of anomeric effects, critical evaluation of the kinetics and reverse anomeric effects, discovery of a new substantial effect in second- and lower-row.
TermsVector search | B–OK. Download books for free. Find books. 5, Books The Anomeric Effect and Related Stereoelectronic Effects at Oxygen.
Springer-Verlag Berlin Heidelberg. Anthony John Kirby (auth.) bond effect chern conformation stereoelectronic anomeric effect effects axial lone The stereoelectronic alignment of course has to be anti-periplanar, and this orientation will control how the anomeric effect operates.
What you may not find in the text books is a C CN bond as the electron acceptor. But if e.g. C F can be one, why not C CN (the cyano group is often described as a pseudo-halogen).Reviews: 7.
Chapter Views are the COUNTER-compliant sum of full text article downloads since November (both PDF and HTML) across all institutions and individuals. The anomeric effect is a chemical phenomenon 1,2,3,4,5,6,7,8,9 that refers to an observed stabilization 10 of six-membered carbohydrate rings when they contain an electronegative substituent at.
Nasrin Masnabadi, Afshin Taghva Manesh and Fatemeh Azarakhshi, Ab Initio Calculations of the Conformational Preferences of 1,3-OxathianeS-Oxide and its Analogs ContainingSandSEAtoms—Evidence for Stereoelectronic Interactions Associated with the Anomeric Effects, Phosphorus, Sulfur, and Silicon and the Related Elements,8, (), ().Cited by: The Anomeric Effect and Related Stereoelectronic Effects at Oxygen A.
Kirby Springer-Verlag, Berlin, Heidelberg, New-York, 3. Carbohydrates, Synthesis, Mechanisms and Stereoelectronic Effects M. Miljkovic Springer, NY, 4. Electostatic and Stereoelectronic Effects in Carbohydrate Chemistry M. Miljkovic Springer, NY, Size: 1MB. Anomeric Effect and Related Stereoelectronic Effects Momcilo Miljkovic.
Oxocarbenium Ion Momcilo Miljkovic. Conformations and Chemistry of Oxocarbenium Ion Momcilo Miljkovic. Armed-Disarmed Concept in the Synthesis of Glycosidic Bond Momcilo Miljkovic.
Stereoelectronic Effects in Nucleosides and Nucleotides Momcilo Miljkovic. 7 Book Edition: 有機化学において、アノマー効果（アノマーこうか、英: anomeric effect ）あるいはエドワード＝レミュー効果（Edward-Lemieux effect）は、立体電子効果の一つである。 シクロヘキサン環内のヘテロ原子に隣接するヘテロ原子性置換基が、立体的考察から予測される障害の少ないエクアトリアル配置で.
Stereoelectronic Effects illustrates the utility of stereoelectronic concepts using structure and reactivity of organic molecules An advanced textbook that provides an up-to-date overview of the field, starting from the fundamental principles Presents a large selection of modern examples of stereoelectronic effects in organic reactivity Shows practical applications of stereoelectronic effects.
Stereoelectronic effects in organic chemistry. 0n that basis acetal function acidic conditions Acta alkoxy group alkyl amide amino aminoester anomeric effect anti peri planar axially oriented B-glycosides bicyclic C—0 bond carbanion carbon carbonyl group carbonyl-oxygen exchange Chem Chim cis isomer cleavage co-workers compound.
Stereoelectronic Effects. Welcome,you are looking at books for reading, the Stereoelectronic Effects, you will able to read or download in Pdf or ePub books and notice some of author may have lock the live reading for some of ore it need a FREE signup process to obtain the book.
If it available for your country it will shown as book reader and user fully subscribe will benefit by. Machine derived contents note: Anomeric Effect: How It Came To Be Postulated, J.T. Edward; Anomeric and Associated Stereoelectronic Effects: Scope and Controversy, G.R.J.
Thatcher; Intramolecular Strategies and Stereoelectronic Effects: Glycosides and Orthoesters Hydrolysis Revisited, P.
Deslongchamps. These are the same interactions associated with the quasi-anomeric effect. (The quasi-anomeric effect, discussed in Section V of Chapter 6, provides an explanation for the conformations adopted by pyranosyl radicals.
27,28) Since these orbital interactions are developing at the transition state, they should be responsible, at least in. The anomeric effect – the key stabilizing force in oxygen containing compounds The anomeric effect, a well-known axial preference of acceptor substituents at the anomeric carbons of pyranoses and related heterocycles with an endocyclic lone pair, is one of the oldest and most-studied stereoelectronic effects 15 (Scheme 1).Cited by: Anomeric and Reverse Anomeric Effect in Acetals and Related Functions F.
Grein Chap DOI: /bkch Publication Date (Print): Novem Effective Molarities for Intramolecular Reactions. Kirby, Adv. Phys. Org. Chem.,17, Key Words: PHYSICAL ORGANIC/MECHANISMS/INTRAMOLECULAR A. Illustrated Glossary of Organic Chemistry Anomeric effect: Originally defined as the tendency of heteroatomic substituents (such as an OH group) adjacent to a heteroatom within a cyclohexane ring to prefer the axial orientation instead of the less hindered equatorial orientation that would be expected from steric considerations alone.
An anomer is a type of geometric variation found at certain atoms in carbohydrate molecules. An epimer is a stereoisomer that differs in configuration at any single stereogenic anomer is an epimer at the hemiacetal/acetal carbon in a cyclic saccharide, an atom called the anomeric carbon.
The anomeric carbon is the carbon derived from the carbonyl carbon compound (the ketone or. Anomeric effect Last updated Janu The α- and β-anomers of D-glucopyranose. In organic chemistry, the anomeric effect or Edward-Lemieux effect is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to a heteroatom within a cyclohexane ring to prefer the axial orientation instead of the less hindered equatorial orientation that would be.
In effect, the C–C glycosylic bond in the dΨU analog likely acts as an insulator to inhibit the flow of electrons from the sugar O4′ to the uracil ring, thus blocking the key coupling of the anomeric and σ-π Arom stereoelectronic effects predicted here by the experimentally defined substrate and product by: bonds, manifests itself in numerous stereoelectronic effects controlling organic structure and reactivity.1,2 In particular, such interactions can deliver electron density to electron-deficient centers and, thus, are often sug-gested to determine stereoselectivity of organic reactions where the transition states for stereodivergent pathways.
Anomeric effects in pyranosides and related acetals. The anomeric effect, originally defined as the preference of an electronegative substituent at the anomeric position of pyranosides to stand in an axial rather than an equatorial position, results from the combination of multiple steric, stereoelectronic and medium interactions Cited by: β‐Silicon effect and related β‐effects n/σ‐Interactions Anomeric effects Reverse anomeric effect “Anomeric effects without lone pairs”: beyond the n → σ* interactions n/π‐Interactions Esters and related carboxylic acid derivatives File Size: 1MB.
The term “anomeric effect” has been used to describe stereo-preferences of sugars 26 and related molecules. 27 Recent work has argued that stereo-preferences are actually a result of destabilizing electrostatic interactions. 28 In this work the role of hyperconjugation in phosphodiester bond length is explored.
The current terminology of Cited by: 5. Summary This chapter illustrates the generality of stereoelectronic concepts, Stereoelectronic Effects in Action Search for more papers by this author. Book Author(s): Igor V.
Alabugin. Department of Chemistry and Biochemistry, Florida State University, USA. Search for more papers by this author. The anomeric effect and associated Stereoelectronic effects The anomeric effect and associated Stereoelectronic effects Tvaroska, Igor CARBOHYDRATE RESEARCH ELSEVIER Carbohydrate Research () C9-C10 Book review The Anomeric Effect and Associated Stereoelectronic Effects, ACS Symposium SeriesEdited by Gregory R.J.