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ISBN-10: 0470771585

ISBN-13: 9780470771587

ISBN-10: 0471996106

ISBN-13: 9780471996101

Chapter 1 contemporary advances within the theoretical remedy 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 resolution 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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0a6 kcal/mole. N-methylacetamide (NMA) (1 1) was studied by Shipman and Christoffersen6 s , using floating spherical gaussian orbitals (FSGO). The lowest energy was obtained f o r a conformation with the N-methyl group cis t o the carbonyl group, a C-methyl group hydrogen eclipsing the CO group, and an N-methyl group hydrogen eclipsing the C-N bond. This C-N bond conformation was also found experimentally8 '. 66 kcal/ mole less stable. 8 kcal/moles5. Note that the conformational behaviour of the N-methyl group upon rotation about the C-N bond is opposite to that of NMF.

The fully extended form (1 80",180") was 4 kcal/mole less stable. IV. CHEMICAL PROPERTIES A. Protonation, Deprotonation and Proton Transfer Consecutive protonation and deprotonation reactions allow one to relate the acidity and basicity of compounds: A:- 1 AH 2 + Step 1 Sfep1 Step 2 S t e p 2' AH2' 2' 1' measures measures measures measures t h e basicity of A-. the acidity of AH. the basicity of AH. t h e acidity of AH;. The energy changes in reactions 1 o r 2 are given by P A , the proton affinity of A - or A H with a positive o r negative sign according t o the thermodynamic convention.

Reproduced with permission from A. C . Hopkinson and 1. G. Csizmadia, 7heoref. Cltim. , 31, 83 (1973). 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 ) .

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Acid Derivatives: Volume 1 (1979)

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