Theoretical studies on empirical structure-reactivity relationship: The Yukawa-Tsuno equation

Journal of Physical Organic Chemistry

Volumn 16, Issue 6, 2003, Pages 323-335

  Nakata, Kazuhide ^a   Fujio, Mizue ^b   Nishimoto, Kichisuke ^c   Tsuno, Yuho ^b  

^a HOSEI UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

ab initio calculation; Benzyl cations; Hydride transfer reaction; Substituent effects; Yukawa Tsuno equation

Indexed keywords

BENZENE; CHARGE TRANSFER; CORRELATION METHODS; ELECTRONIC STRUCTURE; PERTURBATION TECHNIQUES; POSITIVE IONS; REACTION KINETICS; THERMODYNAMIC STABILITY;

YUKAWA-TSUNO EQUATION;

SUBSTITUTION REACTIONS;

EID: 0038274881     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.621     Document Type: Article

References (42)

1. Shorter J. In Correlation Analysis in Chemistry, Chapman NB, Shorter J (eds). Plenum Press: New York, 1978; 119-173; Shorter J. Correlation Analysis of Organic Reactivity. Research Studies Press: Chichester, 1982.
2. Shorter J. In Correlation Analysis in Chemistry, Chapman NB, Shorter J (eds). Plenum Press: New York, 1978; 119-173; Shorter J. Correlation Analysis of Organic Reactivity. Research Studies Press: Chichester, 1982.
3. Tsuno Y, Fujio M. Chem. Soc. Rev. 1996; 25: 129-139.
4. Yukawa Y, Tsuno Y. Bull. Chem. Soc. Jpn. 1959; 32: 971-981.
5. Yukawa Y, Tsuno Y, Sawada M. Bull. Chem. Soc. Jpn. 1966; 39: 2274-2286.
6. Tsuno Y, Fujio M. Adv. Phys. Org. Chem. 1999; 32: 267-385.
7. (a) Nakata K, Fujio M, Saeki Y, Mishima M, Tsuno Y, Nishimoto K. J. Phys. Org. Chem. 1996; 9: 561-572;
8. (b) Nakata K, Fujio M, Saeki Y, Mishima M, Tsuno Y, Nishimoto K. J. Phys. Org. Chem. 1996; 9: 573-582;
9. (c) Nakata K, Fujio M, Mishima M, Tsuno Y, Nishimoto K. J Phys. Org. Chem. 1998; 11: 857-870.
10. (a) Mishima M, Inoue H, Fujio M, Tsuno Y. Tetrahedron Lett. 1989; 30: 2101-2104;
11. (b) Mishima M, Inoue H, Fujio M, Tsuno Y. Tetrahedron Lett. 1990; 31: 685-688;
12. (c) Mishima M, Arima K, Usui S, Fujio M, Tsuno Y. Chem. Lett. 1987; 1047-1050;
13. (d) Mishima M, Usui S, Fujio M, Tsuno Y. Nippon Kagaku Kaishi 1989; 1269-1273;
14. (e) Mishima M, Nakamura H, Nakata K, Fujio M, Tsuno Y. Chem. Lett. 1994; 1607-1610;
15. (f) Mishima M, Usui S, Inoue H, Fujio M, Tsuno Y. Nippon Kagaku Kaishi 1989; 1262-1268;
16. (g) Mishima M, Nakata K, Nomura H, Fujio M, Tsuno Y. Chem. Lett. 1992; 2435-2438;
17. (h) Tashiro H, Kikukawa K, Ikenaga K, Shimizu N, Mishima M. J. Chem. Soc., Perkin Trans. 2 1998; 2435-2440.
18. Hehre WJ, Radom L, Schleyer PvR, Pople JA. Ab initio Molecular Orbital Theory. Wiley: New York, 1986.
19. (a) Wiberg KB. J. Org. Chem. 2002; 67: 4787-4794;
20. (b) Exner O, Bohn S. J. Org. Chem. 2002; 67: 6320-6327;
21. (c) Liptak MD, Gross KC, Seybold PG, Feldgus S, Shields GC. J. Am. Chem. Soc. 2002; 124: 6421-6427;
22. (d) Schindele C, Houk KN, Mayr H. J. Am. Chem. Soc. 2002; 124: 11208-11214.
23. Frisch MJ, Trucks GW, Schlegel HB, Scuseria CE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JJA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.6. Gaussian: Pittsburgh, PA, 1998.
24. Møller C. Plesset MS. Phys. Rev. 1934; 46: 618-622.
25. Becke AD. J. Chem. Phys. 1993; 98: 5648-5652.
26. (a) Pople JA, Krishnan R, Schlegel HB, DeFrees D, Binkley JS, Frisch MJ, Whiteside RF, Hout RF, Hehre WJ. Int. J. Quantum Chem., Symp. 1981; 15: 269-278;
27. (b) Pople JA, Scott AP, Wong MW, Radom L. Isr. J. Chem. 1993; 33: 345-350.
28. Bauschlicher JCW, Partridge H. J. Chem. Phys. 1995; 103: 1788-1791.
29. Taft RW, Topsom RD. Prog. Phys. Org. Chem. 1988; 16: 1-83.
30. Fujio M, Nakashima K, Tokunaga E, Tsuji Y, Tsuno Y. Tetrahedron Lett. 1992; 33: 345-348.
31. (a) Taft RW. J. Phys. Chem. 1960; 64: 1805-1815;
32. (b) Taft RW, Lewis IC. J. Am. Chem. Soc. 1958; 80: 2436-2443;
33. (c) Taft RW, Lewis IC. J. Am. Chem. Soc. 1959; 81: 5343-5352;
34. (d) Taft RW, Ehrenson S, Lewis IC, Glick RE. J. Am. Chem. Soc. 1959; 81: 5352-5361.
35. (a) Brown HC, Okamoto Y. J. Am. Chem. Soc. 1958; 80: 4979-4987;
36. (b) Stock LM, Brown HC. Adv. Phys. Org. Chem. 1963; 1: 35-154;
37. (c) Okamoto Y, Brown HC. J. Org. Chem. 1957; 22: 485-494.
38. Laube T, Olah GA, Bau R. J. Am. Chem. Soc. 1997; 119: 3087-3092.
39. Mulliken RS. J. Chem. Phys. 1955; 23: 1833-1840.
40. O'Brien M, More O'Ferrall RA. J. Chem. Soc., Perkin Trans. 2 1978; 1045-1053; Hammond GS. J. Am. Chem. Soc. 1955; 77: 334-338; Leffler JE, Grunwald E. Rates and Equilibria of Organic Reactions. Wiley: New York, 1963.
41. O'Brien M, More O'Ferrall RA. J. Chem. Soc., Perkin Trans. 2 1978; 1045-1053; Hammond GS. J. Am. Chem. Soc. 1955; 77: 334-338; Leffler JE, Grunwald E. Rates and Equilibria of Organic Reactions. Wiley: New York, 1963.
42. O'Brien M, More O'Ferrall RA. J. Chem. Soc., Perkin Trans. 2 1978; 1045-1053; Hammond GS. J. Am. Chem. Soc. 1955; 77: 334-338; Leffler JE, Grunwald E. Rates and Equilibria of Organic Reactions. Wiley: New York, 1963.