Download PDF by : Acid Derivatives: Volume 1 (1979)

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ISBN-10: 0470771585

ISBN-13: 9780470771587

ISBN-10: 0471996106

ISBN-13: 9780471996101

Chapter 1 fresh advances within the theoretical therapy of acid derivatives (pages 1–58): I. G. Csizmadia, M. R. Peterson, C. Kozmutza and M. A. Robb
Chapter 2 Thermochemistry of acid derivatives (pages 59–66): Robert Shaw
Chapter three Chiroptical homes of acid derivatives (pages 67–120): Rolf Hakansson
Chapter four Mass spectra of acid derivatives (pages 121–174): S. W. Tam
Chapter five Complexes of acid anhydrides (pages 175–212): R. Foster
Chapter 6 Hydrogen bonding in carboxylic acids and derivatives (pages 213–266): Dusan Hadzi and Snegulka Detoni
Chapter 7 The synthesis of carboxylic acids and esters and their derivatives (pages 267–490): Michael A. Ogliaruso and James F. Wolfe
Chapter eight The chemistry of lactones and lactams (pages 491–531): G. V. Boyd
Chapter nine The chemistry of orthoamides of carboxylic acids and carbonic acid (pages 533–599): W. Kantlehner
Chapter 10 Detection and backbone of acid derivatives (pages 601–640): W. H. Prichard
Chapter eleven The photochemistry of natural acids, esters, anhydrides, lactones and imides (pages 641–753): Richard S. Givens and Nissim Levi

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Extra info for Acid Derivatives: Volume 1 (1979)

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G. Csizmadia, M. R. Peterson, C. Kozmutza and M. A. 4 h co l/m o lc FIGURE 12. Computed proton affinities (kcal/mole) of formate ion to give cis formic acid, and cis formic acid to give the cis-trans protonated acid. Reproduced with permission from A. C. Hopkinson, K. Yates and I. G. Csizmadia, J: a e m . , 52,1784 (1970). The hydroxy-protonated tautomer of formic acid is less stable than the carbonyl-protonated tautomer b y some 25 kcal/mole. However, within the carbonylprotonated tautomer (14) there are three conformations.

89 kcal/mole. These results are in agreement with experiment, which gives a 26O angle of rotation for the minimum energy form. Radom and coworkers44 examined acetamide and found t h e lowest energy form to have a methyl H eclipsing the carbonyl group (cf. acetic acid in the previous section). 3 kcal/mole. 3 experimentallya2). 4 e V S O . Turning t o N-substituted amides, the lowest energy conformation of N-methylformamide (NMF) (10) was reported44 t o have the methyl group cis t o the carbonyl group, in agreement with experimenta 3.

R. Peterson, K . Yates and I. G. Csizmadia, Progr. nieoret. Org. , 2 , 162 (1977). 122 2 H - /? : FIGURE 26. Optimum STOJG g e e metry for conformation B (see Figures 23 and 24) of the tetrahedral intermediate. Reproduced with permission from M. H. Lien, A. C. Hopkinson, M. R. Peterson, K. Yates and I. G . Csizmadia, Progr. 77ieoret. Org. , 2, 162 (1977). 0 Low minimum Soddle point between minimum A and C -0 /r! : I High minimum minimum B FIGURE 27. Idealized geometry of approach for hydroxide ion o n methyl formate and the resulting anions.

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Acid Derivatives: Volume 1 (1979)

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