Amino, Nitrosco and Nitro Compounds and Their Derivatives:

Content:
Chapter 1 Structural chemistry (pages 1–51): S. Sorriso
Chapter 2 Stereochemistry and conformations (pages 53–83): Morton Raban and Jeremy Greenblatt
Chapter three The chemistry of ionized amino, nitroso and nitro compounds within the fuel section (pages 85–126): Helmut Schwarz and Karsten Levsen
Chapter four Rearrangements regarding nitroso and nitro compounds (pages 127–153): D. L. H. Williams
Chapter five The spectroscopy, photophysics and photochemistry of saturated amines (pages 155–180): Arthur M. Halpern
Chapter 6 Photochemistry of nitro and nitroso compounds (pages 181–290): Yuan L. Chow
Chapter 7 Radiation chemistry of amines, nitro and nitroso compounds (pages 291–318): Clive L. Greenstock
Chapter eight Electrochemistry of nitro compounds (pages 319–337): Albert J. Fry
Chapter nine Electrochemistry of amines (pages 339–359): Wayne E. Britton
Chapter 10 Radical anion reactions of nitro compounds (pages 361–393): Nathan Kornblum
Chapter eleven Direct aminations (pages 395–416): Tuvia Sheradsky
Chapter 12 Pyrolysis of nitrites, nitrates, nitro compounds, nitroso compounds and amines (pages 417–458): Leslie Batt
Chapter thirteen Nitrones and nitronic acid derivatives: their constitution and their roles in synthesis (pages 459–564): Eli Breuer
Chapter 14 Nitroxides (pages 565–622): Hans Gunter Aurich
Chapter 15 Enamines and ynamines (pages 623–714): G. Pitacco and E. Valentin

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Extra info for Amino, Nitrosco and Nitro Compounds and Their Derivatives: Volume 1 (1982)

Example text

Recall the proviso that changes in structure parameters cannot be explained in terms of resonance alone. 0 ' + 0+/0 CH3-N' CH3-N< C HN ;~ 0 0*O It 111 (20) As regards the possible limiting structures participating in resonance in nitromethane, it is interesting that in this molecule the quadrupole coupling constants158may be explained by a valence bond description in which 'nitrite ion' type structures (20, I) contribute by ca. 20%. 59 (chloropicrin and bromopicrin). According to some author~'~~ this J ~ difference ~, in C-N distance together with the fact that the configuration of the nitro group is very similar to that in free NO2, may be explained by some decomposition in halopicrins.

We have also seen that in aromatic amines there is a correlation between the C-N bond distance and the value of the adjacent C-C bond lengths in the phenyl. 46 S. Sorriso In general the effect of the substituents on the geometry of the phenyl ring has been recognized by various authors231and explored a ~ c u r a t e l y ~ ~In ' - the ~ ~ ~case . of the C-C bond lengths of the phenyl ring in almost all the molecules examined u p until now a rationalization cannot be made because accurate structure determinations are lacking due t o thermal motion.

29. J. H. Bryden, L. A. Burkardt, E. W. Hughes and J. , 9, 573 (1956). 30. F. Iwasaki and H. , B28, 3370 (1972). 31. F. J. Lovas, F. 0. Clark and E. Tiemann, J. Chem. , 62, 1925 (1975). 32. K. Takagi and T. Kojirna, J. Phys. Japan, 30, 1145 (1971). 33. M. Tsuboi, A. Y. Hirakawa and K. Tamagake, J. Mol. Spectry, 22, 272 (1967). 34. J. Kraitchman, Amer. J . , 21, 17 (1953). 35. R. E. Penn and R. J. Olsen, J. Mol. Spectry, 62,423 (1976). 36. R. E. Penn and J. A. Birkenmeier, J. Mol. Spectry, 62,416 (1976).

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