Double-Bonded Functional Groups: Volume 1 (1977)

Content:
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 concerning the X?Y team (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)

Example text

A study of nitro-substituted esters. whose conformational change would affect the dipole moment particularly markedly, did not discover any significant proofZo2,nor did a study of the dielectric loss reveal any change of conformation'". 203 : (i) mesomerism within the functional g r o ~ p ' ~expressed ~ . ' ~ ~ by structure 94; (ii) electrostatic r e p u l ~ i o n of~ ~ nearly ~ . ~parallel ~ ~ dipoles in the E form 92b; (iii) repulsion of lone electron (iv) purely steric hindrance in the same (v) a kind of hydrogen bond2'' stabilizing the Z form 92a.

Note the difference between the significance of these substituents in compounds 55 and the nitro substituent in 54: The former were introduced to enlarge the amount of information, while the nitro group in 54 is an inherent structural feature, without which there would be n o configurational problem. g. 56) until recently. The assignment is based on an 1. Dipole moments of molecules containing X=Y groups 37 X-ray study of N-methyl-4-chlorobenzaldimineN-oxide66 and on other arguments'15; among these even the dipole moment of 56 is completely although the second isomer is not known.

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. From unsymmetrical derivatives benzeneazomethane dioxide (76) and its derivatives were investigated' 5 2 . The high dipole moment is certainly incompatible with the E configuration (76a) and was interpreted in terms of some rotational freedom around the N=N bond'52.

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