Chapter 1 contemporary 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 resources for Acid Derivatives: Volume 1 (1979)
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. Directly the opposite is the case of formic acid (Scheme 1).
A. 8 kcoI/mole kcol(mole H\ ,c\+ H II O+ II NH, Relative energies (kcal/mole) of FIGURE 15. the tautomers of protonated formamide. reported PA values for acetaldehyde and formic acid and it is very hard t o choose among them. However, if we accept -175 kcal/mole for HCOOH and -1 85 kcal/ mole for HCOOCH3 as recommended b y Mills and coworkersg7 then we may use these values t o bracket t h e PA of HCONHl. If we interpolate linearly we obtain a PA value for HCONHz t o be -180 kcal/ mole, while linear extrapolation to HCOF gives a PA value of -170 kcal/mole.
1, 77 (1976), or R. McWeeny and B. T. Sutcliffe, hethods of Molecular Quantum Mechanics, Academic Press, New York, 1969, Chap. C. J. Roothaan, Rev. Mod. , 23. 69 (1951). 2. J. Paldus, J. Ozem. , 61,5321 (1975) or M. J. Downward and M. A. Robb, nieoret. Chim. Acta, 46, 129 (1977). 3. The force may b e calculated from equations given in P. Pulay,Mol. , 17. 197 (1969). 4. E. B. Wilson, J. C. Decius and P. C. Cross, Molecular Vibrutions. McGraw-Hill, New York, 1955. 5. D. F. Mclntosh and M. R. Peterson, General Vibrational Analysis Program, Program No.