Browse > Article
http://dx.doi.org/10.5012/bkcs.2008.29.9.1769

Pyridinolysis of O-Aryl Phenylphosphonochloridothioates in Acetonitrile  

Lumbiny, Bilkis Jahan (Department of Chemistry, Inha University)
Adhikary, Keshab Kumar (Department of Chemistry, Inha University)
Lee, Bon-Su (Department of Chemistry, Inha University)
Lee, Hai-Whang (Department of Chemistry, Inha University)
Publication Information
Bulletin of the Korean Chemical Society / v.29, no.9, 2008 , pp. 1769-1773 More about this Journal
Abstract
fThe kinetics and mechanism of the reactions of Y-O-aryl phenylphosphonochloridothioates with X-pyridines are investigated in acetonitrile at 35.0 ${^{\circ}C}$. The negative value of the cross-interaction constant, $\rho$XY = −0.46, indicates that the reaction proceeds by concerted $S_N2$ mechanism. The observed $k_H/k_D$ values involving d-5 pyridine ($C_5D_5N$) nucleophiles are greater than unity (1.05-1.11). The net primary deuterium kinetic isotope effects, $(k_H/k_D)_{net}$ = 1.28-1.35, excluding the increased $pK_a$ effect of d-5 pyridine are obtained. The transition state with a hydrogen bond between the leaving group Cl and the hydrogen (deuterium) atom in the C-H(D) is suggested for the studied reaction system.
Keywords
O-Aryl phenylphosphonochloridothioates; Pyridinolysis; Cross-interaction constant; Deuterium kinetic isotope effect
Citations & Related Records
Times Cited By KSCI : 5  (Citation Analysis)
Times Cited By Web Of Science : 42  (Related Records In Web of Science)
Times Cited By SCOPUS : 44
연도 인용수 순위
1 Lee, H. W.; Guha, A. K.; Lee, I. Int. J. Chem. Kinet. 2002, 34, 632   DOI   ScienceOn
2 Dey, N. K.; Han, I. S.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 2003   DOI   ScienceOn
3 Hoque, M. E. U.; Dey, N. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Org. Biomol. Chem. 2007, 5, 3944   DOI   ScienceOn
4 Hengge, A. C.; Onyido, I. Curr. Org. Chem. 2005, 9, 61   DOI   ScienceOn
5 Kumara Swamy, K. C.; Satish Kumar, N. Acc. Chem. Res. 2006, 39, 324   DOI   ScienceOn
6 Um, I. H.; Park, J. E.; Shin, Y. H. Org. Biomol. Chem. 2007, 5, 3539   DOI   ScienceOn
7 Guha, A. K.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1999, 765
8 Holtz, K. M.; Catrina, I. E.; Hengge, A. C.; Kantrowitz, E. R. Biochemistry 2000, 39, 9451   DOI   ScienceOn
9 Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Phys. Org. Chem. 2008, 21, 544   DOI   ScienceOn
10 Um, I. H.; Shin, Y. H.; Han, J. Y.; Mishima, M. J. Org. Chem. 2006, 71, 7715   DOI   ScienceOn
11 Guha, A. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 12   DOI   ScienceOn
12 Lee, H. W.; Guha, A. K.; Kim, C. K.; Lee, I. J. Org. Chem. 2002, 67, 2215   DOI   ScienceOn
13 Adhikary, K. K.; Lee, H. W.; Lee, I. Bull. Korean Chem. Soc. 2003, 24, 1135   DOI   ScienceOn
14 Adhikary, K. K.; Lumbiny, B. J.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 851   DOI   ScienceOn
15 Thatcher, G. R. J. Adv. Phys. Org. Chem. 1989, 25, 99   DOI
16 Williams, A. Concerted Organic and Bio-Organic Mechanisms; CRC Press: Boca Raton, 2000; Chapter 7-8
17 Hengge, A. C. Acc. Chem. Res. 2002, 35, 105   DOI   ScienceOn
18 Hengge, A. C. Adv. Phys. Org. Chem. 2005, 40, 49   DOI
19 Zalatan, J. F.; Catrina, I.; Mitchell, R.; Grzyska, P. K.; O'Brien, P. J.; Herschlay, D.; Hengge, A. C. J. Am. Chem. Soc. 2007, 129, 9789   DOI   ScienceOn
20 Albert, A.; Serjeant, E. P. The Determination of Ionization Constants, 3rd ed.; Chapman and Hall: New York, 1984
21 Onyido, I.; Albright, K.; Buncel, E. Org. Biomol. Chem. 2005, 3, 1468   DOI   ScienceOn
22 Dean, J. A. Handbook of Organic Chemistry; McGraw-Hill: New York, 1987; Chapter 8
23 Hehre, W. J.; Random, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; Chapter 4
24 Charton, M. Prog. Phys. Org. Chem. 1987, 16, 287   DOI
25 Dunn, E. J.; Buncel, E. Can. J. Chem. 1989, 67, 1440   DOI
26 Dunn, E. J.; Moir, R. T.; Buncel, E.; Purdon, J. G.; Bannard, R. A. B. Can. J. Chem. 1990, 68, 1837   DOI
27 Buncel, E.; Albright, K. G.; Onyido, I. Org. Biomol. Chem. 2004, 2, 601   DOI   ScienceOn
28 Perrin, C. I.; Engler, R. E. J. Phys. Chem. 1991, 95, 8431   DOI
29 Perrin, C. I.; Ohta, B. K.; Kuperman, J. J. Am. Chem. Soc. 2003, 125, 15008   DOI   ScienceOn
30 Onyido, I.; Swierczek, K.; Purcell, J.; Hengge, A. C. J. Am. Chem. Soc. 2005, 127, 7703   DOI   ScienceOn
31 Liu, Y.; Gregersen, B. A.; Hengge, A. C.; York, D. M. Biochemistry 2006, 45, 10043   DOI   ScienceOn
32 Gregersen, B. A.; Lopez, X.; York, D. M. J. Am. Chem. Soc. 2003, 125, 7178   DOI   ScienceOn
33 Crumpler, T. B.; Yoh, J. H. Chemical Computations and Errors; John Wiley: New York, 1940; p 178
34 Oivanen, M.; Ora, M.; Lonnberg, H. Collect. Czech. Chem. Commun. 1996, 61, S-1   DOI
35 Melander, L.; Saunders, W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley-Interscience: New York, 1980
36 Poirier, R. A.; Youliang, W.; Westaway, K. C. J. Am. Chem. Soc. 1994, 116, 2526   DOI   ScienceOn
37 Li, Y.; Bao, R.; Zhang, Z.; Yang, J.; Cao, J.; Jiang, X. Huaxue Xuebao 1987, 45(7), 696
38 Tsao, L.; Chzhou, Ch.; Sun, Ts.; Koroteev, A. M. Russian J. Org. Chem. 2003, 39(11), 1608   DOI   ScienceOn
39 Purnanand; Batra, B. S. Indian J. Chem. 1992, 31B(11), 778
40 Purnanand; Batra, B. S.; Lal, G. Tetrahedron Letters 1994, 35(26), 4641   DOI   ScienceOn
41 Hoque, M. E. U.; Dey, N. K.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 1797   DOI   ScienceOn
42 Hoque, M. E. U.; Dey, S.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Org. Chem. 2007, 72, 5493   DOI   ScienceOn
43 Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 936   DOI   ScienceOn
44 Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57
45 Lee, I.; Lee, H. W. Collect. Czech. Chem. Commun. 1999, 64, 1529   DOI   ScienceOn
46 Lee, I. Chem. Soc. Rev. 1990, 19, 317   DOI
47 Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165   DOI
48 Perrin, C. I.; Ohta, B. K.; Kuperman, J.; Liberman, J.; Erdelyi, M. J. Am. Chem. Soc. 2005, 127, 9641   DOI   ScienceOn
49 Hondal, R. J.; Bruzik, K. S.; Zhao, Z.; Tsai, M. D. J. Am. Chem. Soc. 1997, 119, 5477   DOI   ScienceOn
50 Lee, I.; Kim, C. K.; Li, H. G.; Sohn, C. K.; Kim, C. K.; Lee, H. W.; Lee, B. S. J. Am. Chem. Soc. 2000, 122, 11162   DOI   ScienceOn