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 houses 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)
Peterson, C. Kozmutza and M . A. 97 kcal/mole for trans-NMA). E. Biological Molecules One class of biological molecules of great importance is the amino acids. Glycine, +NH3CH2CO0 ;and polypeptides of glycine have been the subject of several ab initio inves'tigations. Ryan and Whittenas performed calculations o n t h e planar conformers of the glycine and glycylglycine zwitterions, and found that n o major redistribution of electronic charge occurs upon dimerization (formation of t h e peptide bond).
T h e in-plane oxygen) protonation resulted in a greater energy lowering than either the T O or n N protonation' 0 4 . This finding was in agreement b i t h earlier work involving electrostatic potential contours' 0 5 . Similar findings were reported10G for the interaction of formamide and other cations such as Na+ and K+. Theoretical studies of protonation of other acid derivatives such as esters and anhydrides have not been made. However, an experimental study on the P A values 1. R e c e n t advances in t h e theoretical treatment of acid derivatives I -160- I 41 I - I I 0 I - 1901 I I 6 ATOMIC FIGURE 16.
H I I I min2 TS3 minl Turning t o the protonation of formamide, the first question is the site of protonation. There are two possibilities: 0-protonation and N-protonation. A number of papers’ O 3 dealing with the problem reported computed proton affinities indicating t h a t 0-protonated formamide is more stabie than :he N-protonated tautomer (see Figure 15) by some 6 kcal/mole. I c H\ I H+ 4 O+ 0 II C H H / \ N I H / H II H Although the observation that the 0-protonated teutomer is more stable than the N-protonated one is believed t o be significant, the numerical values of the proton affinities are probably too large due t o the use of a moderate basis set and limited geometry optimization.
Acid Derivatives: Volume 1 (1979)