Molecular basis of LFER: Theoretical study of polar substituent effect in aliphatic series

Journal of Physical Organic Chemistry

Volumn 20, Issue 9, 2007, Pages 662-670

  Ponec, Robert ^a   Van Damme, Sofie ^b  

^a INSTITUTE OF CHEMICAL PROCESS FUNDAMENTALS   (Czech Republic)

^b GHENT UNIVERSITY   (Belgium)

Author keywords

Feld effect; Nature of inductive effect

Indexed keywords

CARBOXYLIC ACIDS; ELECTRIC FIELDS; QUANTUM CHEMISTRY;

NATURE OF INDUCTIVE EFFECT; PROTON AFFINITY;

FREE ENERGY;

EID: 34848859569     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1228     Document Type: Article

References (49)

1. Ingold CK. Structure and Mechanism in Organic Chemistry, Chapter II. Cornell University Press: Ithaca, NY, 1953.
2. Taft RW. J. Phys. Chem. 1960; 64: 1805-1815.
3. Hine J. Physical Organic Chemistry, Chapter 2, 2nd edn. Mc Graw Hill: New York, 1962.
4. Baker FW, Parish RC, Stock LM. J. Am. Chem. Soc. 1967; 89: 5677-5685.
5. Golden R, Stock LM. J. Am. Chem. Soc. 1966; 88: 5928-5929.
6. Wilcox CF, Leung C. J. Am. Chem. Soc. 1968; 90: 336-341.
7. Stock LM. J. Chem. Educ. 1972; 49: 400-404.
8. Bowden K. Can. J. Chem. 1963; 41: 2781-2793.
9. Bowden K. J. Chim. Phys. 1992; 89: 1647-1659.
10. Bowden K, Grubbs EJ. Chem. Soc. Rev. 1996; 171-177.
11. Charten M. J. Phys. Org. Chem. 1999; 12: 275-282.
12. Exner O, Fiedler P. Coll. Czech. Chem. Commun. 1980; 45: 1251-1268.
13. Böhm S, Exner O. Coll. Czech. Chem. Commun. 2004; 69: 984-995.
14. Exner O, Friedl Z. Prog. Phys. Org. Chem. 1993; 19: 259-294.
15. Exner O. J. Phys. Org. Chem. 1999; 12: 265-274.
16. Bowden K, Grubbs JE. Progr. Phys. Org. Chem. 1993; 19: 183-224.
17. Roberts JD, Carboni RA. J. Am. Chem. Soc. 1955; 77: 5554-5558.
18. Kirkwood JG, Westheimer FH. J. Chem. Phys. 1938; 6: 506-512.
19. Kirkwood JG, Westheimer FW. J. Chem. Phys. 1938; 6: 513-517.
20. Orttung W. J. Am. Chem. Soc. 1978; 100: 4369-4375.
21. Ponec R, Kučera J. Chem. Scripta 1984; 22: 152-154.
22. Ponec R, Gironés X, Carbó-Dorca R. J. Chem. Inf. Comp. Sci. 2002; 42: 564-570.
23. Longuet-Higgins HC. Rec Trav. Chim. 1956; 75: 825-835.
24. Roberts JD, Moreland TW. J. Am. Chem. Soc. 1953; 75: 2167-2173.
25. Cramer Ch, Truhlar DG. Chem. Rev. 1999; 99: 2161-2200.
26. Silva CO, da Silva EC, Nascimento NA. J. Phys. Chem. A 2000; 104: 2404-2409.
27. Schurmann G, Cossi M, Barone V, Tomasi J. J. Phys. Chem. A 1998; 102: 6706-6712.
28. Wiberg KB. J. Org. Chem. 2002; 76: 1613-1617.
29. Exner O, Böhm S. Chem. Eur. J. 2003; 9: 4718-4723.
30. Exner O, Böhm S. J. Phys. Org. Chem. 2006; 19: 393.
31. Exner O, Böhm S. J. Phys. Org. Chem. 2004; 17: 124.
32. Exner O, Böhm S. Curr. Org. Chem. 2006; 10: 763-778.
33. Krygowski TM, Stepien BT. Chem. Rev. 2005; 105: 3482-3512.
34. Liu L, Fu Y, Li RQ, Guo QX. J. Chem. Inf. Comp. Sci. 2004; 44: 652-657.
35. Nolan EM, Linck RG. J. Am. Chem. Soc. 2000; 122: 11497-11506.
36. Nolan EM, Linck RG. J. Phys. Chem. A 2001; 105: 7297-7307.
37. Nolan EM, Linck RG. J. Phys. Chem. A 2002; 106: 533-543.
38. Campanelli AR, Domenicano A, Ramondo F. J. Phys. Chem. A 2006; 110: 10122-10129.
39. Boys SF. Mol. Phys. 1970; 19: 553-566.
40. Bjerrum NJ. Z. Phys. Chem. 1923; 106: 219-242.
41. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani M, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Kiene M, Li X, Knox JE, Hratchian HP, Cross JP, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski W, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi K, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill MPW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision B.05. Gaussian, Inc., Pittsburgh, PA, 2003.
42. Scrocco E, Tomasi J. Top. Curr. Chem. 1973; 42: 95-167.
43. Charton M. Prog. Phys. Org. Chem. 1981; 13: 119-251.
44. Siegel S, Komarmy JM. J. Am. Chem. Soc. 1960; 82: 2547-2553.
45. Cole TW, Mayers C, Stock LM. J. Am. Chem. Soc. 1974; 96: 4555-4557.
46. Koppel IA, Mishima M, Stock LM, Taft RW, Topsom RD. J. Phys. Org. Chem. 1993; 6: 685-689.
47. Adcock W, Baran Y, Filipi A, Speranza M, Trout NA. J. Org. Chem. 2005; 70: 1029-1034.
48. Palm VA. Osnovy kolichestvennoi teorii organicheskikh reakcii, Chapter VII. Izdatelstvo Khimiya: Leningrad, 1967;
49. Wiberg KB. J. Org. Chem. 2002; 67: 1613-1617.