Role of hydrogen-bonded nucleophiles in aromatic nucleophilic substitutions in aprotic solvents. Reactions of halonitrobenzenes with ethylenediamine, 3-dimethylamino-1-propylamine and histamine in toluene

Journal of Physical Organic Chemistry

Volumn 18, Issue 8, 2005, Pages 880-885

  Alvaro, Cecilia E Silvana ^a   Nudelman, Norma Sbarbati ^b  

^a UNIVERSIDAD NACIONAL DEL COMAHUE   (Argentina)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Aprotic solvents; Aromatic nucleophilic substitution; Dimer nucleophile mechanism; Hydrogen bond; Hydrogen bonded nucleophiles; Mixed aggregates

Indexed keywords

DIMERS; HYDROGEN BONDS; MOLECULAR STRUCTURE; SOLVENTS; SUBSTITUTION REACTIONS; SURFACE TREATMENT; SYNTHESIS (CHEMICAL);

APROTIC SOLVENTS; AROMATIC NUCLEOPHILIC SUBSTITUTION; DIMER NUCLEOPHILE MECHANISMS; HYDROGEN-BONDED NUCLEOPHILES; MIXED AGGREGATES;

AROMATIC COMPOUNDS;

EID: 22544463686     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.957     Document Type: Review

References (40)

1. Desiraju G, Steiner T. The Weak Hydrogen Bond. Oxford University Press: New York, 1999.
2. Scheiner S. Hydrogen Bonding. Oxford University Press: New York, 1997.
3. Filarowski A, Koll A, Karpfen A, Wolschann P. Chem. Phys. 2004; 297: 323-332.
4. Ki Rhee S, Hoon Kim S, Lee S, Young Lee J. Chem. Phys. 2004; 297: 21-29.
5. Katritzky AR, Fara DC, Yang H, Tämm K, Tamm T, Karelson M. Chem. Rev. 2004; 104: 175-198.
6. Palm N, Palm V. Russ. J. Org. Chem. 2000; 36: 1075.
7. Reichardt C. Chem. Rev. 1994; 94: 2319.
8. Abboud J-LM, Notario R. Pure Appl. Chem. 1999; 71: 645-718.
9. Marcus Y. Chem. Soc. Rev. 1993; 22: 409-416.
10. Raczynska ED, Wozniak K. Trends Org. Chem. 1998; 7: 159-172.
11. Zou J-W, Yu Q-S, Shang Z-C. Wuji Huaxue Xuebao 2000; 58: 1247.
12. Zou J-W, Shang Z-C, Yu Q-S. Wuji Huaxue Xuebao 2001; 14: 51.
13. Zhao W-N, Shang Z-C, Zou J-W, Guo M, Yu Q-S. Wuji Huaxue Xuebao 2002; 18: 726.
14. Katritzky A, Tamm T, Wang Y, Sild S, Karelson M. J. Chem. Inf. Comput. Sci. 1999; 39: 684.
15. Spange S, Vilsmeier E, Fischer K, Reuter A, Prause S, Zimmermann Y, Schmidt Ch. Macromol. Rapid Commun. 2000; 21: 643.
16. Terrier F. Nucleophile Aromatic Displacement: The Influence of the Nitro Group, in Organic Nitro Chemistry Series, Ferrer H (ed). VCH Publishers: New York, 1991.
17. Nudelman NS. In The Chemistry of Amino, Nitroso, Nitro and Related Groups, Patai S (ed). Wiley: Chichester, 1996; 1215-1300.
18. (a) Nudelman NS, Savini M, Alvaro CES, Nicotra V, Yankelevich JS, J. Chem. Soc. Perkin Trans. 2 1999; 1627-1630;
19. (b) Nudelman NS, Alvaro CES, Savini M, Nicotra V, Yankelevich JS. Collect. Czech. Chem. Commun. 1999; 64: 1583-1593.
20. (a) Mancini PME, Fortunato G, Adam C, Vottero LR, Terenzani AJ. J. Phys. Org. Chem. 2002; 15: 258-269;
21. (b) Mancini PME, Adam C, Perez A, del C, Vottero LR. J. Phys. Org. Chem. 2000; 13: 221-231.
22. (a) Boga C, Forlani L. J. Chem. Soc. Perkin Trans. 2 2001; 1408-1413;
23. (b) Forlani L, Boga C, Forconi M. J. Chem. Soc. Perkin Trans. 2 1999; 1455-1458.
24. Nudelman NS. J. Phys. Org. Chem. 1989; 2: 1-14.
25. Chiacchiera SM, Singh JO, Anunziata JD, Silver JJ. J. Chem. Soc. Perkin Trans. 2 1988; 1585-1589.
26. (a) Forlani L. In The Chemistry of Amino, Nitroso, Nitro and Related Groups, Patai S (ed). Wiley: Chichester, 1996; 423-477;
27. (b) Forlani L. J. Phys. Org. Chem. 1999; 12: 417-424.
28. Sugiyama N, Hayami J. Chem. Soc. Jpn. 1999; 691-692.
29. Rao CN, Pradeep T. Chem. Soc. Rev. 1991; 20: 477.
30. Ramondo F, Bencivenni L, Portalone G, Domenicano A. Struct. Chem. 1994;5: 1.
31. Llamas-Saiz AL, Foces-Foces C, Elguero J. J. Mol. Struct. 1994; 328: 297.
32. (a) Nudelman NS, Palleros D. Acta Sud. Am. Quim. 1981; 1: 125;
33. (b) Nudelman NS, Palleros D. J. Org. Chem. 1983; 48: 1607.
34. Hirst J. J. Phys. Org. Chem. 1994; 7: 68.
35. Nudelman NS, Montserrat JM. J. Chem. Soc. Perkin Trans. 2 1990; 1073-1076.
36. Nudelman NS, Alvaro CES, Yankelevich JS. J. Chem. Soc. Perkin Trans. 2 1997; 2125-2130.
37. Weast RC (ed). Handbook of Chemistry and Physics (57th edn). CRC Press, Inc: Cleveland, Ohio, USA; 1977.
38. Nudelman NS, Marder M, Gurevich A. J. Chem. Soc. Perkin Trans. 2 1993; 229-233.
39. Vogel A. Practical Organic Chemistry (4th edn). Longman Inc: New York, USA; 1978: 526.
40. Bunnet JF, Kato T, Nudelman NS. In Fundamental Organic Chemistry Laboratory Manual, Finley KT, Wilson J (eds). Prentice-Hall: New Jersey, 1974, 112.