Chapter 1 Dipole moments, configurations and conformations of molecules containing X?Y teams (pages 1–92): Otto Exner
Chapter 2 Liquid crystals with X?Y teams (pages 93–129): J. P. Van Meter
Chapter three Thermochemistry of X?Y teams (pages 131–147): Robert Shaw
Chapter four Mechanisms of removal and addition reactions related to the X?Y crew (pages 149–329): Anthony F. Cockerill and Roger G. Harrison
Chapter five The electrochemistry of X?Y teams (pages 331–368): Albert J. Fry and Roberta Gable Reed
Chapter 6 1,3?Dipolar cycloadditions concerning X?Y teams (pages 369–532): Giorgio Bianchi, Carlo De Micheli and Remo Gandolfi
Chapter 7 Reactions of carbenes with X?Y teams (pages 533–651): Alan P. Marchand
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Extra resources for Double-Bonded Functional Groups: Volume 1 (1977)
The steric arrangement of dibenzalacetone involves configuration on twca C=C bonds and conformation on two C-C bonds. It was solved rather tentatively from dipole moments alone, although several substituted derivatives were available*64. Measurement of the Kerr constant165 favoured the a p conformation on C-C and E configurations on C=C. A. The conformation on the central bond of I ,2-dicarbonyl compounds has been the subject of much discussion. The definitely non-zero dipole 1. Dipole moments of molecules containing X=Y groups 49 moments of biacetyl, benzil, oxalyl chloride, ethyl oxalate, and many other similar compounds can in principle be accounted for by: (i) mixture of the sp and a p forms; (ii) one non-planar form; (iii) free rotation; (iv) an anomalous atomic polarization (if the observed dipole moment is not too large).
39 ilcn,c = The configurational problem of N-chloroimines (32a, b) was not solved in such a convincing manner, since the difference between the isomers is rather small6'. 96 D). The problem unsubstituted benzophenone-N-~hloroimine~~ woufd be worth reinvestigating on a broader experimental basis. 26 Otto Exner CYH. 95 (33) Another chloroimine (33) inay serve as an example of overestimating the dipole moment r n e t h ~ d " Even ~ . when the N H 2 group is assumed to be planar, there are still configurations on three double bonds to be determined in addition to conformations on two C-N bonds.
However, this estimation was wrong15'. The value claimed14' (1-63D) is thus certainly too high but a recalculation was not made; the E configuration (74) seems possible'50. 3-Nitroso-3-methyl-2-butanone exists as the dimer (75)even in solution. Its dipole moment was i n t e r ~ r e t e d ' ~as' a mixture of the E form (75) and the 2 form, assuming free rotation around the C-N and C-C bonds. However, the assumption and calculations are far from reliable. Hence the virtually zero dipole moment of E azoniethane dioxide'50 is the only one known with certainty; the 2 isomer was too unstable to be measured.