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Content: v. 1. Three-membered heterocycles, together with all fused systems containing a three-membered heterocyclic ring / volume editor, Albert Padwa -- v. 2. Four-membered heterocycles together with all fused systems containing a four-membered heterocyclic ring / volume editor, Christian Stevens -- v. 3. Five-membered rings with one heteroatom together with their benzo and other carbocyclic-fused derivatives / volume editors, Gurnos Jones, Christopher A. Ramsden -- v. 4. Five-membered rings with two heteroatoms, each with their fused carbocyclic derivatives / volume editor, John Joule -- v. 5. Five-membered rings: triazoles, oxadiazoles, thiadiazoles and their fused carbocyclic derivatives / volume editor, Viktor V. Zhdankin -- v. 6. Other five-membered rings with three or more heteroatoms, and their fused carbocyclic derivatives / volume editor, Viktor V. Zhdankin -- v. 7. Six-membered rings with one heteroatom, and their fused carbocyclic derivatives / volume editor, David StC. Black -- v. 8. Six-membered rings with two heteroatoms, and their fused carbocyclic derivatives / volume editor, R. Alan Aitken -- v. 9. Six-membered rings with three or more heteroatoms, and their fused carbocyclic derivatives / volume editor, Kenneth Turnbull -- v. 10. Ring systems with at least two fused heterocyclic five- or six-membered rings with no bridgehead heteroatom / volume editor, Ray C.F. Jones -- v. 11. Bicyclic 5-5 and 5-6 fused ring systems with at least one bridgehead (ring junction) N / volume editor, Janine Cossy -- v. 12. Five- and six-membered fused systems with bridgehead (ring junction) heteroatoms concluded: 6-6 bicyclic with one or two N or other heteroatoms; polycyclic; spirocyclic / volume editor, Keith Jones -- v. 13. Seven-membered heterocyclic rings and their fused derivatives / volume editor, George R. Newkome -- v. 14. Eight-membered and larger heterocyclic rings and their fused derivatives, other seven-membered rings / volume editor, George R. Newkome -- v. 15. Cumulative subject index
E-Book Content
7.01 Pyridines and their Benzo Derivatives: Structure J. B. Harper University of New South Wales, Sydney, NSW, Australia ª 2008 Elsevier Ltd. All rights reserved. 7.01.1 Introduction 7.01.2 Molecular Characteristics 1 2 7.01.2.1 Theoretical Methods 2 7.01.2.2 Experimental Structural Methods 4 7.01.2.3 Spectroscopic Methods 5 7.01.2.3.1 7.01.2.3.2 7.01.2.3.3 7.01.2.3.4 7.01.2.3.5 7.01.2.4 5 6 7 7 7 Thermodynamic Studies 7.01.2.4.1 7.01.2.4.2 7.01.2.4.3 7.01.3 Nuclear magnetic resonance Ultraviolet/Vis spectroscopy Infrared spectroscopy Mass spectrometry Photoelectron spectroscopy 8 Tautomerism Conformation Solvation and solvent effects 8 8 11 Supramolecular Characteristics 11 7.01.3.1 Extended Pyridine Derivatives 11 7.01.3.2 Interactions in Solution 16 7.01.3.2.1 7.01.3.2.2 7.01.3.3 7.01.4 Host–guest complexes Rotaxanes and catenanes 16 22 Crystal Engineering: Interactions in the Solid State Summary 27 35 References 35 7.01.1 Introduction As for CHEC(1984) and CHEC-II(1996) this section covers the structure of pyridine, along with derivatives substituted at either nitrogen or carbon. Particularly, this will include the benzosubstituted derivatives such as quinolines and isoquinolines, along with bipyridyl systems. In addition, the saturated derivatives (such as piperidines) will also be covered. While the valence isomers of pyridine have been considered through computation (for example, see ), the structures are not reported and, as such, these compounds will not be dis