Synthesis and stereochemistry of benzamidines and acetamidines

Arkivoc

Volumn 2000, Issue 3 SPEC.ISS., 2000, Pages 320-342

  Oberlander, Eva A ^a   Tebby, John C ^a  

^a STAFFORDSHIRE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; AMIDE; AMIDINE; BENZAMIDINE DERIVATIVE; METHYL GROUP;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHIRALITY; MOLECULAR MECHANICS; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; POLYMERIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

EID: 3042599242     PISSN: 14246376     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Oberlander, E. A.; Tebby, J. C. Heteroatom Chem., 1998, 9, 261.
2. Atherton, F. R.; Morrison, A. L.; Cremlyn, R. J. W.; Kenner, G. W.; Todd, A. R.; Webb, R. F. Chem. And Ind., 1955, 1183.
3. Cramer, F. D.; Weinmann, G. Chem. and Ind., 1960, 46.
4. (a) Cremlyn, R. J. W.; Kenner, G. W.; Todd A. R. Soc., 1960, 4511.
5. b) Atherton, F. R. EP 782267 (1954).
6. C. Zioudrou; Tetrahedron, 1962, 18, 197.
7. (a) Perkow, W. DAS 1067433 (1957). Samarai, L. I.; Kolodyazhnyi, D. I.; Vishnevskii, O. V; Derkach, G. I.Zh. Obshch. Khim., 1970, 40, 750.
8. (a) Perkow, W. DAS 1067433 (1957). Samarai, L. I.; Kolodyazhnyi, D. I.; Vishnevskii, O. V; Derkach, G. I.Zh. Obshch. Khim., 1970, 40, 750.
9. (b) Look, M.J. Agric. Food Chem., 1980, 28, 888.
10. Wiesboeck, R. A. 1968, US 3393253.
11. Zabirov, N. G.; Pozdeev, O. K.; Shamsevaleev, F. M.; Cherkasov R. A.; Gilmanova, G. H. Khim. Farm. Zh., 1989, 600.
12. (a) Efremov, D. A.; Zavlin, P. M.; Tebby, J. C. "Phosphoric Anhydride: Structure, Chemistry and Applications" Pub. Wiley 1998, 121 - 126.
13. (b) Smith, J. R. L.; Norman, R. O. C.; Rose, M. E.; Curran, A. C. W.J. Chem. Soc., Perkin Trans. 1, 1979, 1185.
14. (a) Steinkopf, W. B., 1908, 41, 3571.
15. (b) Kirsanov, A. V.; Makitra, R. G. Zh. Obshch. Khim., 1957, 27, 450.
16. Mizrahi, V.; Modro, T. A. J. Org. Chem., 1982, 47, 3533.
17. Zimin, M. G.; Afanasyev; M. M.; Pudovik, A. N. Zh. Obshch. Khim., 1979, 49, 2621.
18. (e) Onisko, P. P.; Shuvalova, E. A.; Chudakova, T. I.;
19. (f) Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim., 1989, 59, 2138.
20. Zavlin, P. M.; Efremov, D. A.; Govorkov, A. L. Zh. Obshch. Khim., 1992, 62, 220.
21. llaBenzanilide has its HOMO and HOMO-1 similar to formamide but its HOMO -2 has the electron density on the amide group restricted to the carbonyl p-bond. HOMO -5 has delocalisation across all three atoms of the amide group.The partial charge on N was slightly larger for formamide (-0.45) than for benzanilide (-0.37) the charges on O being the same (-0.30) [HF STO-3G). Electrostatic potentials although considerably higher in magnitude followed the same trends.
22. "The Chemistry of the Amide Group" Ed. Zabicky, J., Pub. Interscience 1970;
23. a) Chapter 1 "Molecular and electronic structure of the amide group" by Robin, M. B. Bovey F. A. and Barsch H.
24. b) Chapter 2 "Acid, base and complexing properties of amides" by Homer R. B. andJohnson C. D.",
25. Chapter 3 "Reactions of the Carboxamide group" by Challis B. C. and Challis J. A..
26. (a) Jugie, G.; Smith J. A.; Martin, J. J. Chem. Soc., Perkin II 1975, 925.
27. (b) Tebby, J. C.; Willetts, S. E. Phosphorus and Sulfur, 1987, 30, 292.
28. (a) Leistner, S.; Vieweg, S.; Vieweg, H.; Strohsheidt, T. Pharmazie, 1991, 46, 415.
29. (b) Khokhlov, P. S. K.; Kashemirov, B. A.; Mikitjuk, A. D.; Chimishkjan, A. L.; Strepikheev, Yu. A., Zh. Obshch. Khim., 1984, 54, 2701.
30. -1 less stable than the amide structure.
31. We acknowledge the assistance of Dr M. C. Salt in performing the acid catalysed experiments.
32. Baraniak, J.; Stec, W. J. Phosphorus Sulfur, 1986, 29, 115.
33. Baraniak, J.; Stec, W. J. Tetrahedron Lett., 1991, 32, 137, 4193.
34. Mazurkiewicz, R., Acta Chim. Hung., 1990, 127, 439.