Read e-book online Amidines and Imidates: Volume 1 (1975) PDF

ISBN-10: 0470771496

ISBN-13: 9780470771495

ISBN-10: 0471669237

ISBN-13: 9780471669234

Content:
Chapter 1 common and theoretical features of amidines and imidic acid derivatives (pages 1–84): G. Hafelinger
Chapter 2 structure, configurational and conformational facets, and chiroptical homes of imidic acid derivatives (pages 85–155): G. Fodor and B. A. Phillips
Chapter three Detection and backbone of imidic acid derivatives (pages 157–188): W. H. Prichard
Chapter four Rearrangements concerning imidsc acid derivatives (pages 189–240): C. G. McCarty and L. A. Garner
Chapter five The electrochemistry of Imsdic esters and amidines (pages 241–253): Henning Lund
Chapter 6 organic reactions and pharmaceutical makes use of of imidic acid derivatives (pages 255–281): Raymond J. Grout
Chapter 7 coaching and artificial makes use of of amidines (pages 283–348): Jean?Albert Gautier, Marcel Miocque and Claude Combet Farnoux
Chapter eight Kinetics and mechanisms of reactions of amidines (pages 349–384): Robert H. de Wolfe
Chapter nine Imidates together with cyclic imidates (pages 385–489): Douglas G. Neilson
Chapter 10 The chemistry of amidrazones (pages 491–545): okay. M. Watson and D. G. Neilson
Chapter eleven Estimation of the thermochemistry of imidic acid derivatives (pages 547–564): Robert Shaw
Chapter 12 advanced formation, H?bonding and basicity of imidic acid derivatives (pages 565–617): J. Sevcik and F. Grambal

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Additional info for Amidines and Imidates: Volume 1 (1975)

Sample text

For amidrazones two tautomeric forms (39) and (40) are possible. I 1 C C -N 4 \- - - N-N- I (39) 1 -N -/ \ - N-N- I I (40) Table 8 shows the results of the HMO-calculation for both forms with the parameters of equation 9. For both isomers three bonding MO’s and one antibonding MO filled with six x-electrons are obtained. The x-bond energy is higher for the tautomer (40) indicating a higher degree of stability In this compound the charge distribution is more smoothed out. TABLE 7. Results of the HMO-calculation for imidic acid derivatives with the heteioatom parameters from eq Compound 1 21 i Ej C // \3 X- - a: cj1 (B) cj2 cj3 ,hot, Enbond (B> (8) 41 42 q3 51 52 -N- x = c1 Imidoyl chlorides 1 2 x=s Thioimidates 1.

0-CH, 1646(CHC13)”‘ R-C // NH CaHs-C \ OR’ 1655-1652(Rarnan)11~ CeHs-C, O-CH2 \ VH2 O-CHZ 1650118 N- -C NH // OR 1653-1648(Rarnan)115 N-CHz 167O1la 1565(CCi4)108 1663(CHC13)lo8 16211a /N-CH, // CBHS-C, \- s- S-CH, 1622(CHCI,)”‘ 7-CH2 H3C-C I ceHs-c~-iHz \ \S-CH2 S-CHz 16401l’ 1613”’ I 607(CHC13)’14 1S80(CHCl3)”‘ 1. Aspects of amidines and imidic acid derivatives 53 conjugation lowers the vibration frequency except in the case of the diconjugated methyl N-phenylbenzimidate108. Quarternization raises the frequency of the C = N double bond.

The deviations are generally less than the standard deviations given for the equations (10). The C = N double bond length is decreasing in the order: amidinium cations > amidines > amidrazones > imidates > thioimidates > imidoyl chlorides > imines. The C-N single bond length decreases in the order amides > amidines > amidinium cations. 5. Effect of phenyl substitution on amidines The x-bond energies of phenyl-substituted planar amidines listed in Table 10 may only be compared directly for systems of equal size.

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Amidines and Imidates: Volume 1 (1975)


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