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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Additional info for Acid Derivatives: Volume 1 (1979)
For the latter compound, Pople and coworkers' found that the conformation with the plane of the amide group twisted ' ' p 7 6 ' 1. 79 kcal/mole more stable than the all-planar structure. 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).
Yates and I. G. Csizmadia, Progr. Theorer. Org. , 2, 162 (1977). 0- 60 - 2401 300 b, - 0 1 . R e c e n t advances in the theoretical treatment of acid derivatives 3 FIGURE 25. Pseudo-threedimensional representation of the conformational energy surface for the tetrahedral intermediate. The minima are shown in the lower projection. Reproduced with permission from M. 14. Lien, A. C . Hopkinson, M. R. Peterson, K . Yates and I. G. Csizmadia, Progr. nieoret. Org. , 2 , 162 (1977). 122 2 H - /? : FIGURE 26.
1. Recent advances in the theoretical treatment of acid derivatives 49 0 W 0 -2c E \ - s -4c Y $ -6C 5 -8C lx w w t- a -1OC J 2 -12C -14C FIGURE 22. Computed reaction profile for the attack of OH- on formamide. Reproduced with permission from G. Alagona, E. Scrocco and J. Tomasi. J. Amer. Uzem. , 97, 6976 (1975). An ab initio s t u d y o n the base-catalysed hydrolysis of methyl formate has recently been reported' 2 3 involving the mechanism shown in equation (6 I ) . Most 0 I1 C / \ H - 0- I -0 H OCH3 CIIIIIOH H' - HCOOH + - O W 3 - HCOO- + HOCH3 (611 'oCH3 of the work has focused o n t h e stereochemistry of the first intermediate (15).