's Amides (1970) PDF

ISBN-10: 0470771232

ISBN-13: 9780470771235

ISBN-10: 0471980498

ISBN-13: 9780471980490

Content:
Chapter 1 Molecular and digital constitution of the amide staff (pages 1–72): M. B. Robin, F. A. Bovey and Harold Basch
Chapter 2 Synthesis of amides (pages 73–185): A. L. J. Beckwith
Chapter three Acid?base and complexing homes of amides (pages 187–243): R. B. Homer and C. D. Johnson
Chapter four Rearrangement and removing of the amido staff (pages 245–288): Joseph F. Bieron and Frank J. Dinan
Chapter five Photochemistry of the amido workforce (pages 289–308): Ionel Rosenthal
Chapter 6 Radiation chemistry of amides (pages 309–334): Owen H. Wheeler
Chapter 7 Chemistry of imidic compounds (pages 335–381): Owen H. Wheeler and Oscar Rosado
Chapter eight The chemistry of thioamides (pages 383–475): W. Walter and J. Voss
Chapter nine The chemistry of the thiohydrazide workforce (pages 477–514): W. Walter and ok. J. Reubke
Chapter 10 The chemistry of hydrazides (pages 515–600): Hans Paulsen and Dieter Stoye
Chapter eleven organic formation and reactions of the amido team (pages 601–684): J. E. Reimann and R. U. Byerrum
Chapter 12 Directing and activating results of the amido crew (pages 685–729): J. A. Shafer
Chapter thirteen Reactions of the carboxamide crew (pages 731–857): Brian G. Challis and Judith A. Challis

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Example text

A. Eovcy, and Harold Basch bis-trimethylacetamide complcx of PtCl,, a n d found the ligand to have the iminol form with Pt-NH=C coordination. F. r. spectra of amides. 1. r. studies of self-association of molecules capable of hydrogen bonding have becn carried out. These depend upon marked deshielding of the protons involved i n the hydrogen bond. Y . Qualitatively, this may bc understood as arising because the electrostatic field of the hydrogen bond tends to draw H towards Y and repel the X-H bonding electrons towards X, resulting in a reduced elcctron density about H.

We have already indicated that the principal reason for this state of affairs is that the rate constants near coalescence can be dctermined fairly accurately, while at other temperatures the errors of the measurements are such as to tip the Arrhenius plot towards lower values of A H t and consequently more negative values of AS*. It is notable that the most recent and most careful measurements yield the hishest values of 4W and less negative or even positive values of A S . icult to understand, as, on the basis of the resonance formulation (3and 4), the transition state should be less polar and less solvated than the ground state.

Hammaker and Guglcr 6 4 have suggested that. for N,N-diethylacetam:de the conformation 21 is prcferred, wliilc for N, N-diisopropylarnides, the methyl groups are turiicd away from the N atom as in 22. - H3C 'C---H O>C-N/ H' H3C H--2 'C-CH, H (211 0 \ H,C' H\ \ C-N / 9 4 3 ' C-CH, \ H / % x 3 (22 1 Conformation 21 appcars to be consistent with steric requircmcnts, but It has becn further suggested64 that they are supportcd by thc chcmical shifts of the CH, and C H protons compared to thosc of thc methyl groups, but in view of the unccrtain rationalc of chemical shifts of AT-alkyl protons, this cannot be considered strong support.

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Amides (1970)


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