Acid Derivatives: Volume 1 (1979)

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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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E. ), Znferafomic Distances, Special Publication No. 11, The Chemical Society, London, 1958; Supplement, Special Publication No. 18, T h e Chemical Society, London, 1965. 8. J. E. T. Worth, F. T. Marchese and M. E. Conrad, nzeoret. a i m . Acta, 36, 195 (1975). 9. R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. , 54,724 (1971). 10. A. Geffrey, L. Radom and 3. A. Pople, Carbohydrate Res.. 25, 117 (1972). 11. I. G. Csizmadia, M. C. Harrison and B. T. Z. T. Quart Progr. Repf.. 50, 4 (1963); Theoret.

For example t h e following four reported PA values of HCOGH spread over a range of 1 7 kcal/mole: -16298, -16699, -17S1Oo, -179"'. TABLE 14. Experimental basicities of somc carboxylic acids Acid -Proton affinity" (kcal/molc) HCOOH CH, COOH CH,CH,COOH F, ccoo1-i 175 188 190 167 - "Reference 97. Besides energetics there are stereochemical questions associated with protonation. One of t h e most important questions is the site of protonation. In the case of formate ion both oxygen atoms are equivalent, thus there is no chance for the formation of more than one tautomer.

2 kcal/mole)* O . As far as the proton transfer is concerned we may distinguish two processes: the single proton transfer and the double proton transfer. In the single proton transfer we generate an ion pair: and clearly such a charge separation is an unfavourable process from energetic considerations. The double proton transfer however will regenerate the original situation: 44 I. G. Csizmadia, M. R. Peterson, C. Kozmutza and M. A. e. EDt= 0). Only the barrier height of this interconversion will determine the feasibility of this double proton transfer.

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