Ab initio study of the effect of α-substituents on the acidity of cyclopropabenzene

Journal of Physical Organic Chemistry

Volumn 18, Issue 8, 2005, Pages 763-772

  Eckert Maksic, Mirjana ^a   Glasovac, Zoran ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Ab initio calculations; Basicity; Cyclopropabenzenyl anions; Cyclopropenyl anions; Substituent effects

Indexed keywords

ALKALINITY; ANNEALING; BENZENE; FLUORINE; MAGNETIC RESONANCE; PROTONS;

AB INITIO CALCULATIONS; CYCLOPROPABENZENYL ANIONS; CYCLOPROPENYL ANIONS; SUBSTITUENT EFFECTS;

AROMATIC COMPOUNDS;

EID: 22544433205     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.930     Document Type: Review

References (68)

1. Battiste MA, Coxon JM. In The Chemistry of the Cyclopropyl Group, Rappoport Z (ed). Wiley: Chichester, 1987; 255-303.
2. Buncel E, Dust JM. Carbanion Chemistry: Structures and Mechanisms. Oxford University Press: Oxford, 2003, and references cited therein.
3. (a) Chou PK, Dahlke GD, Kass SR. J. Am. Chem. Soc. 1993; 115: 315-324;
4. (b) Wiberg KB, Castejon H. J. Org. Chem. 1995; 60: 6327-6334;
5. (c) Peerboom RAL, de Koning LJ, Nibbering NMM. J. Am. Soc. Mass Spectrom. 1994; 5: 159-168;
6. (d) Bartmess JE, Wilson B, Sorensen DN, Bloor JE. Int. J. Mass Spectrom. Ion Processes 1992; 117: 557-563.
7. (a) Han S, Hare MC, Kass SR. Int. J. Mass Spectrom. 2000; 201: 101-108;
8. (b) Sachs RK, Kass SR. J. Am. Chem. Soc. 1994; 116: 783-784.
9. Moore L, Lubinski R, Baschky MC, Dahlke GD, Hare M, Arrowood T, Glasovac Z, Eckert-Maksic M, Kass SR. J. Org. Chem. 1997; 62: 7390-7396.
10. Antol I, Glasovac Z, Hare MC, Eckert-Maksic M, Kass SR. Int. J. Mass Spectrom. 2003; 222: 11-26.
11. Eckert-Maksic M, Glasovac Z. Pure Appl. Chem. in press.
12. (a) Sinanoglu O. Tetrahedron Lett. 1988; 29: 889-892;
13. (b) Haiton B, Halton MP. Tetrahedron 1973; 29: 1717-1720;
14. (c) Eaborn C, Stamper JG. J. Organomet. Chem. 1980; 192: 155-161.
15. (a) Halton B. Chem. Rev. 2003; 103: 1327-1369;
16. (b) Halton B. In The Chemistry of the Cyclopropyl Group, vol. 2, Rappoport Z (ed). Wiley: Chichester, 1995; 707-772;
17. (c) Halton B. Pure Appl. Chem. 1990; 62: 541-546;
18. (d) Halton B. Chem. Rev. 1989; 89: 1161-1185;
19. (e) Halton B, Stang PJ. Acc. Chem. Res. 1987; 20: 443-448.
20. (a) Halton B, Randall CJ, Gainsford GJ, Stang PJ. J. Am. Chem. Soc. 1986; 108: 5949-5956;
21. (b) Halton B, Dixon GM. Org. Lett. 2002; 4: 4563-4565;
22. (c) Halton B, Boese R, Dixon GM. Tetrahedron Lett. 2004; 45: 2167-2170;
23. (d) Halton B, Dixon GM. Org. Biomole. Chem. 2004; 2: 3139-3149.
24. (a) Møller C, Plesset MS. Phys. Rev. 1934; 46: 618-622;
25. (b) Pople JA, Binkley JS, Seeger R. Int. J. Quantum Chem. Symp. 1976; 10: 1-19.
26. Scott AP, Radom L. J. Phys. Chem. 1996; 100: 16502-16513.
27. (a) Maksic ZB. In Theoretical Models of Chemical Bonding, vol. 2, Maksic ZB (ed). Springer: Berlin, 1991; 137;
28. (b) Pauling L. J. Am. Chem. Soc. 1931; 53: 1367-1400.
29. McWeeny R. Coulson's Valence (3rd edn). Oxford University Press: Oxford, 1979.
30. Reed AE, Curtiss LA, Weinhold F. Chem. Rev. 1988; 88: 899-926;
31. Glendening ED, Badenhoop JK, Reed AE, Carpenter JE, Bohmann JA, Morales CM, Weinhold F. NBO 5.0. Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2001; http://www.chem.wisc.edu/~nbo5.
32. Bader RWF. Atoms in Molecules: A Quantum Theory. Oxford University Press: Oxford, 1990.
33. Löwdin P-O. J. Chem. Phys. 1950; 18: 365-375.
34. Jiao H, Schleyer PvR. Angew. Chem. Int. Ed. Engl. 1996; 35: 2383-2386;
35. Schleyer PvR, Maerker Ch, Dransfeld A, Jiao H, van Eikema Hommes NJR. J. Am. Chem. Soc. 1996; 118: 6317-6318;
36. Subramanian G, Schleyer PvR, Jiao H. Angew. Chem. Int. Ed. Engl., 1996; 35: 2638-2641.
37. Ditchfield R. Mol. Phys. 1974; 27: 789-807;
38. Cheesman JR, Trucks GW, Keith TA, Frisch MJ. J. Chem. Phys. 1996; 104: 5497-5509.
39. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, 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, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, 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, 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.11.1. Gaussian: Pittsburgh, PA, 2001.
40. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA. J. Comput. Chem. 1993; 14: 1347-1363.
41. (a) Taft RW, Topsom RD. Prog. Phys. Org. Chem 1987; 16: 1;
42. (b) Taft RW. Chem. Rev 1991; 91: 165-195.
43. Wiberg KB. J. Chem. Educ. 1996; 73: 1089-1095.
44. Dahlke GD, Kass SR. J. Am. Chem. Soc. 1991; 113: 5566-5573.
45. Schleyer PvR, Clark T, Kos A, Spitznagel GW, Rohde C, Arad D, Houk KN, Rondan NG. J. Am. Chem. Soc. 1984; 106: 6467-6475.
46. (a) Schleyer PvR, Kos A. Tetrahedron 1983; 24: 1141-1150;
47. (b) Salzner U, Schleyer PvR. Chem. Phys. Lett. 1992; 190: 401-406;
48. (c) Streitwieser A, Holtz D, Ziegler GR, Straffer GR, Brokaw ML, Guibé F. J. Am. Chem. Soc. 1976; 98: 5229-5234;
49. (d) Andreades S. J. Am. Chem. Soc. 1964; 86: 2003-2010.
50. Hopkinson AC, Lien MH. J. Org. Chem. 1981; 46: 998-1003.
51. (a) Bartmess JE, Scott JA, McIver RT Jr. J. Am. Chem. Soc. 1979; 101: 6046-6056;
52. (b) Filley J, DePuy CH, Bierbaum VM. J. Am. Chem. Soc. 1987; 109: 5992-5995;
53. (c) Matimba HEK, Crabbendam AM, Ingemann S, Nibbering NMM. Int. J. Mass Spectrom. Ion Processes 1992; 114: 85-97.
54. Cumming JB, Kebarle P. J. Am. Chem. Soc. 1978; 78: 1835-1838.
55. Taft RW, Koppel IA, Topsom RD, Anvia F. J. Am. Chem. Soc. 1990; 112: 2047-2052.
56. Exner O, Ingr M, Carsky P. J. Mol. Struct.: Theochem. 1997; 397: 231-238.
57. Mariot S, Silvestro A, Topsom RD. J. Mol. Struct.: Theochem. 1989; 184: 23-31.
58. (a) Eckert-Maksić M, Maksić ZB. In Theoretical and Computational Chemistry, Politzer P, Maksic ZB (eds), vol 6, The Chemistry of Cyclobutene, Rappoport Z, Liebman J (eds). Wiley: New York, 2005; 17-82;
59. (b) Maksic ZB, Eckert-Maksić M, Mó O, Yáñez M. In Pauling's Legacy - Modern Modelling of the Chemical Bond, Maksić ZB, Orville-Thomas WJ (eds). Elsevier: Amsterdam, 1999; 47.
60. (a) Mo O, Yáñez M, Eckert-Maksic M, Maksic ZB. J. Org. Chem. 1995; 60: 1638-1646;
61. (b) Eckert-Maksić M, Maksić ZB, Hodošček M, Poljanec K. Int. J. Quantum Chem. 1992; 42: 869-877;
62. (c) Maksic ZB, Eckert-Maksić M, Pfeifer K-H, J. Mol. Strut. 1993; 300: 445-453;
63. (d) Koch W, Eckert-Maksić M, Maksić ZB. J. Chem. Soc., Perkin Trans. 2 1993; 2195-2202;
64. Eckert-Maksić M, Glasovac Z, Maksić ZB. J. Organomet. Chem. 1998; 571: 65-75;
65. (e) Eckert-Maksić M, Maksić ZB, Klessinger M. J. Chem. Soc., Perkin Trans. 2, 1994; 285-289.
66. Merrill GN, Kass SR. J. Am. Chem. Soc. 1997; 119: 12322-12337.
67. Bent HA. Chem. Rev. 1961; 61: 275-311.
68. Kraka E, Cremer D. In Theoretical Models of Chemical Bonding, Part 2, Maksić ZB (ed). Springer: Berlin, 1990, 453-542, and references cited therein.