Stereoelectronic Effects A Bridge Between Structure and Reactivity 1st Edition by Igor Alabugin 1118906349 9781118906347

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Product details:

ISBN 10: 1118906349

ISBN 13: 9781118906347

Author: Igor V. Alabugin

 

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 in asymmetric catalysis, photochemical processes, bioorganic chemistry and biochemistry, inorganic and organometallic reactivity, supramolecular chemistry and materials science

Stereoelectronic Effects A Bridge Between Structure and Reactivity 1st Table of contents:

1 Introduction

1.1 Stereoelectronic effects – orbital interactions in control of structure and reactivity

1.2 Orbital interactions in theoretical chemistry

1.3 The birth of stereoelectronic concepts in organic chemistry

References

2 Direct Effects of Orbital Overlap on Reactivity

2.1 Bond formation without bond breaking: types of overlap in two-orbital interactions

2.2 Bond formation coupled with bond breaking

2.3 Stereoelectronics of supramolecular interactions

References

3 Beyond Orbital Overlap

3.1 Electronic count: two-electron, one-electron and three-electron bonds

3.2 Isovalent vs. sacrificial conjugation

3.3 Neutral, negative, and positive hyperconjugation

References

4 Computational and Theoretical Approaches for Studies of Stereoelectronic Effects

4.1 Quantifying orbital interactions

4.2 Localized orbitals from delocalized wavefunctions

References

5 General Stereoelectronic Trends – Donors, Acceptors, and Chameleons

5.1 Three types of delocalization: conjugation, hyperconjugation, and σ-conjugation

5.2 Geminal and vicinal interactions

5.3 Stereoelectronic main rule: antiperiplanarity

5.4 Scales of donor and acceptor ability of orbitals: polarization, hybridization, and orbital energy effects

5.5 Cooperativity of stereoelectronic effects and antiperiplanar lone pair hypothesis (ALPH) theory – several donors working together

5.6 Summary

References

6 Stereoelectronic Effects with Donor and Acceptor Separated by a Single Bond Bridge

6.1 σ/σ-Interactions

6.2 σ/π-Interactions

6.3 p/σ-Interactions

6.4 n/σ-Interactions

6.5 n/π-Interactions

6.6 π/π-Interactions

References

7 Stereoelectronic Effects with Donor and Acceptor Separated by a Vinyl Bridge

7.1 σ/σ* interactions

7.2 σ/π interactions: allenes vs. alkenes

7.3 Vinyl halides and their carbanions (transition from σC-H → σ*C-Hal to nC → σ*C-Hal interactions)

7.4 Diazenes and the isomerization of azo compounds

7.5 Antiperiplanarity in coordinated bond-breaking and bond-forming processes: eliminations, fragmentations and additions

7.6 Syn-periplanarity: the second best choice

References

8 Remote Stereoelectronic Effects

8.1 Extended through space interactions: homoconjugation and homohyperconjugation

8.2 Double hyperconjugation and through-bond interactions

8.3 Combined through-bond and through-space interactions

8.4 Symmetry and cooperativity effects in cyclic structures

References

9 Transition State Stabilization with Stereoelectronic Effects

9.1 Torquoselectivity

9.2 Diastereoselection in nucleophilic addition to carbonyl compounds and other π-systems

9.3 Electrophilic addition to enamines

9.4 Hyperconjugative assistance to alkyne bending and alkyne cycloadditions

9.5 Negative conjugation – donation from oxygen lone pairs to breaking bonds

9.6 Remote lone pairs in radical reactions: fragmentations

References

10 Stereoelectronic Effects in Reaction Design

10.1 Static stereoelectronics

10.2 Dynamic stereoelectronics

References

11 Stereoelectronic Effects in Action

11.1 Gauche effect (σ → σ* interactions)

11.2 Trans-effect – the cousin of gauche effect in organometallic chemistry

11.3 Anomeric effects (n → σ* interactions)

11.4 Bioorganic chemistry and enzyme reactions

References

12 Probing Stereoelectronic Effects with Spectroscopic Methods

12.1 Infrared spectroscopy

12.2 Nuclear magnetic resonance spectroscopy

12.3 Conclusion

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Igor Alabugin,Stereoelectronic,Effects,Structure