Carbon-Nitrogen Double Bonds (1970)

Chapter 1 normal and theoretical features (pages 1–60): C. Sandorfy
Chapter 2 equipment of formation of the carbon?nitrogen double bond (pages 61–147): Shlomo Dayagi and Yair Degani
Chapter three research of azomethines (pages 149–180): David J. Curran and Sidney Siggia
Chapter four The optical rotatory dispersion and round dichroism of azomethinies (pages 181–234): R. Bonnett
Chapter five uncomplicated and complex?forming houses (pages 235–253): J. W. Smith
Chapter 6 Additions to the azomethine team (pages 255–298): Karou Harada
Chapter 7 Cycloaddition reactions of carbon–nitrogen double bonds (pages 299–326): Jean?Pierre Anselme
Chapter eight Substitution reactions on the azomethine carbon and nitrogen atoms (pages 327–362): R. J. Morath and Gardner W. Stacy
Chapter nine syn?anti Isomerizations and rearrangements (pages 363–464): C. G. McCarty
Chapter 10 Cleavage of the carbon–nitrogen double bond (pages 465–504): Albert Bruylants and Mrs. E. Feytmants?de Medicis
Chapter eleven Electrochemistry of the carbon–nitrogen double bond (pages 505–564): Henning Lund
Chapter 12 Photochemistry of the carbon?nitrogen double bond (pages 565–596): Gunnar Wettermark
Chapter thirteen Imidoyl halides (pages 597–662): R. Bonnett
Chapter 14 Quinonediimines and similar compounds (pages 663–729): ok. Thomas Finley and L. okay. J. Tong

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895 c- 1*105 N 1 . General and Thcoretical Aspccts 21 I t is interesting in this respect to invoke an idea originally due to Sanderson4* which thcn became a crucial point in orbital electronegativity theories. According to it, since the electronegativity of an atom in a niolecule depends on its charge density q, the electronegativities of both atoms bonded together must hecome equal. Subsequently this idea has been applied to the tonding atomic orbitals rather than the whole eleciron distribution around the atoms.

50 3 if the C=N distance is taken as 1-30 A. 24. It is instructive to rewrite the ground state wave function in terms of valence-bond structures. 707xB) (2) where 1 and 2 represent the coordinates of electron 1 and 2 respectively. B. CB+ 25% t, tB 50% c,+ c g 2% 20 C . Sandorfy The share of the ionic structures is highly exaggerated, a well-known defect of the simple Huckel MO method. 616xc + 0 . ~~OXN(~)XN(~) + 0 . 5yo 47% It is seen that the difference between the weight of C N - and C - N i is equal to the effective negative charge on the nitrogen (24y0).

I n 1956 Fabian, Legrand and PoirierlOO published an extensive review o n the infrared and Raman spectra of imines. T h e following two tables are reproduced from their paper. Table 12 gives a general view of C=N band frequencies and Table 13 gives C=N stretching frequencies in amidines. Reference 100 should be consulted for details. 1. Gcncral and Tlicorciical Aspects TABLE 11. C=N 39 infrared stretching frequencies (conjugatcd). 5 1655 1657 1656 1640 1625 1627 1611 1655 - 1658 1646 1628 1639 1619 Oximes have somewhat wider frequency-ranges but do not differ greatly from the imines in their C=N frequency.

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