Browse > Article
http://dx.doi.org/10.5012/bkcs.2014.35.3.753

Kinetics and Mechanism of the Anilinolysis of Aryl N,N-Dimethyl Phosphoroamidochloridates in Acetonitrile  

Barai, Hasi Rani (Department of Chemistry, Inha University)
Lee, Hai Whang (Department of Chemistry, Inha University)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.3, 2014 , pp. 753-757 More about this Journal
Abstract
The nucleophilic substitution reactions of Y-aryl N,N-dimethyl phosphoroamidochloridates with substituted anilines and deuterated anilines are kinetically investigated in acetonitrile at $65.0^{\circ}C$. A stepwise mechanism with a rate-limiting leaving group departure from the intermediate is proposed based on the positive ${\rho}_{XY}$ value. The deuterium kinetic isotope effects involving deuterated anilines show secondary inverse with all the nucleophiles, rationalized by a dominant backside nucleophilic attack.
Keywords
Phosphoryl transfer reaction; Anilinolysis; Aryl N,N-dimethyl phosphoroamidochloridates; Deuterium kinetic isotope effects; Cross-interaction constant;
Citations & Related Records
Times Cited By KSCI : 9  (Citation Analysis)
연도 인용수 순위
1 (d) Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 936.   DOI
2 (a) Guha, A. K.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1999, 765.
3 (b) Lee, H. W.; Guha, A. K.; Lee, I. Int. J. Chem. Kinet. 2002, 34, 632.   DOI   ScienceOn
4 (c) 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
5 (e) Hoque, M. E. U.; Dey, N. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Org. Biomol. Chem. 2007, 5, 3944.   DOI   ScienceOn
6 (f) 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
7 (g) Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Phys. Org. Chem. 2009, 22, 425.   DOI   ScienceOn
8 (h) Hoque, M. E. U.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Org. Biomol. Chem. 2009, 7, 2919.   DOI   ScienceOn
9 (j) Adhikary, K. K.; Lumbiny, B. J.; Dey, S.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 2628.   DOI
10 (k) Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2012, 33, 663.   DOI   ScienceOn
11 (d) Westaway, K. C. Adv. Phys. Org. Chem. 2006, 41, 217.
12 (e) Villano, S. M.; Kato, S.; Bierbaum, V. M. J. Am. Chem. Soc. 2006, 128, 736.   DOI   ScienceOn
13 (f) Gronert, S.; Fagin, A. E.; Wong, L. J. Am. Chem. Soc. 2007, 129, 5330.   DOI   ScienceOn
14 (a) Yamata, H.; Ando, T.; Nagase, S.; Hanamura, M.; Morokuma, K. J. Org. Chem. 1984, 49, 631.   DOI
15 (b) Zhao, X. G.; Tucker, S. C.; Truhlar, D. G. J. Am. Chem. Soc. 1991, 113, 826.   DOI
16 (c) Poirier, R. A.; Wang, Y.; Westaway, K. C. J. Am. Chem. Soc. 1994, 116, 2526.   DOI   ScienceOn
17 Crumpler, T. B.; Yoh, J. H. Chemical Computations and Errors; John Wiley: New York, 1940; p 178.
18 (a) Guha, A. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 12.   DOI   ScienceOn
19 (b) 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
20 (c) Lumbiny, B. J.; Adhikary, K. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 1769.   DOI
21 (g) Hoque, M. E. U.; Lee, H. W. Int.J. Chem. Kinet. 2013, 45, 337.   DOI   ScienceOn
22 (d) Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, H. W. J. Phys. Org. Chem. 2010, 23, 1022.   DOI   ScienceOn
23 (f) Barai, H. R.; Lee, H. W. Bull. Korean Chem. Soc. 2012, 33, 270.   DOI
24 (a) 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
25 (b) Han, I. S.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 889.   DOI
26 (a) Lee, I. Chem. Soc. Rev. 1990, 19, 317.   DOI
27 (b) Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57.
28 (c) Lee, I.; Lee, H. W. Collect. Czech. Chem. Commun. 1999, 64, 1529.   DOI   ScienceOn
29 (a) Lee, I.; Koh, H. J.; Lee, B. S.; Lee, H. W. J. Chem. Soc., Chem. Commun. 1990, 335.
30 (b) Lee, I. Chem. Soc. Rev. 1995, 24, 223.   DOI   ScienceOn
31 (c) Marlier, J. F. Acc. Chem. Res. 2001, 34, 283.   DOI   ScienceOn
32 (e) Hoque, M. E. U.; Dey, S.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 1138.   DOI
33 (i) Dey, N. K.; Lee, H. W. Bull. Korean Chem. Soc. 2010, 31, 1403.   DOI