Synthetic popularity reflects chemical reactivity

Journal of Physical Organic Chemistry

Volumn 22, Issue 9, 2009, Pages 897-902

  Kowalczyk, Bartlomiej ^a   Bishop, Kyle J M ^a   Smoukov, Stoyan K ^a   Grzybowski, Bartosz A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Linear free energy relationships; Organic chemistry; Structure activity relationship; Substituent effect; Synthesis design

Indexed keywords

LINEAR FREE ENERGY RELATIONSHIPS; ORGANIC CHEMISTRY; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTITUENT EFFECT; SYNTHESIS DESIGN;

CHEMICAL REACTIVITY; FREE ENERGY; GRAFTING (CHEMICAL); SYNTHESIS (CHEMICAL);

CHEMISTRY;

EID: 68949207785     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1535     Document Type: Article

References (37)

1. J. Devillers, Comparative QSAR, Taylor & Francis, New York, 1998.
2. L. B. Kier, L. Hall, Molecular Connectivity in Structure Activity Relationships, Research Studies Press, Letchworth, 1986.
3. R. Ponec, L. Amat, R. Carbo-Dorca, J. Phys. Org. Chem. 1999, 12, 447-454.
4. M. Karelson, V. S. Lobanov, A. R. Katritzky, Chem. Rev. 1996, 96, 1027-1043.
5. R. B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 1965, 87, 395-397.
6. R. Hoffman, Angew. Chem., Int. Ed., 2004, 43, 6586-6590.
7. K. Fukui, H. Fujimoto, Frontier Orbitals and Reaction Paths: Selected Papers of Kenichi Fukui, World Scientific Publishing Co., Singapore, 1998.
8. B. A. Grzybowski, A. V. Ishchenko, C. Y. Kim, G. Topalov, R. Chapman, D. W. Christianson, G. M. Whitesides, E. I. Shakhnovich, Proc. Natl. Acad. Sci. 2002, 99, 1270-1273.
9. B. A. Grzybowski, A. V. Ishchenko, J. Shimada, E. I. Shakhnovich, Acc. Chem. Res. 2002, 35, 261-269.
10. M. Fialkowski, K. J. M. Bishop, V. A. Chubukov, C. J. Campbell, B. A. Grzybowski, Angew. Chem., Int. Ed. 2005, 44, 7263-7269.
11. K.J. M. Bishop, R. Klajn, B. A.Grzybowski, Angew. Chem., Int. Ed. 2006, 45, 5348-5354.
12. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, VCH, New York, 1976.
13. F.A.Carey, R. J.Sundberg, Advanced Organic Chemistry, Plenum Press, New York, 1993.
14. L. P. Hammett, Chem. Rev. 1935, 17, 125-136.
15. L. P. Hammett, J. Am. Chem. Soc. 1937, 59, 96-103.
16. Ortho-substituents do not follow Hammett's equation because of additional steric effects.
17. The net electronic effect of substituent × considered as the sum of two distinct effects: induction and resonance. The effect of resonance is greater for para than for meta substituents due to better conjugation of electron pairs in the para position. In contrast, inductive effects, which result from the polarization of bonds, are stronger for meta than for para substituents, which are more distant from the reaction site. Consequently, the Hammett constant s depends not only on the particular substituent but also on the substituent's position and is measured separately for meta and para positions (denoted as oop, respectively).
18. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
19. For other X's the reaction counts are below 5.
20. A. F. Hegarty, The chemistry of diazonium and diazo groups, In The Chemistry of Functional Groups, (Ed.: S. Patai) Wiley, New York, 1978.
21. H. H. Jaffe, Chem. Rev. 1953, 53, 191-261.
22. S. Ueno, T. Suzuki, J. Soc. Chem. Ind. (Japan) 1933, 36B, 615.
23. H. Zollinger, Azo and Diazo Chemistry - Aliphatic and Aromatic Compounds, Interscience Publishers, London, 1961.
24. A. L. Casado, P. Espinet, J. Am. Chem. Soc. 1998, 120, 8978-8985.
25. P. Espinet, A. M. Echavarren, Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
26. V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595.
27. M. B. Smith, J. March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, (6th edn), John Wiley, New York, 2007.
28. O. C. M. Davis, F. W. Rixon, J. Chem. Soc. 1915, 107, 728.
29. A. V. Willi, R. E. Robertson, Can. J. Chem. 1953, 31, 361.
30. S. Proch, Y. Mei, J. M. R. Villanueva, Y. Lu, A. Karpov, M. Ballauff, R. Kempe, Adv. Synth. Catal. 2008, 350, 493.
31. K. Ingold, S. Natshaw, J. Chem. Soc. 1936, 222.
32. E. Tommila, Ann. Acad. Sci. Fennicae 1942, A69, No.3.
33. D. P. Evans, J. J. Gordon, H. B. Watson, J. Chem. Soc. 1937, 1430.
34. K. Bowden, S. P. Hiscocks, M. K. Reddy, J. Chem. Soc., Perkin. Trans. 2 1997, 1133.
35. R. Prihod'ko, M. Sychev, I. Kolomitsyn, P. J. Stobbelaar, E. J. M. Hensen, R. A. van Santen, Microporous Mesoporous Mater. 2002, 56, 241.
36. C. Kooymaen, R. Vanh Helden, A. F. Bickel, Koninkl. Ned. Akad. Wetenschap. Proc. 1953, 56B, 75.
37. D. S. Sivia, J. Skilling, Data Analysis: A Bayesian Tutorial, Oxford University Press, New York, 2006.