Using three major criteria to evaluate aromaticity of five-member C-containing rings and their Si-, N-, and P-substituted aromatic heterocyclics

Structural Chemistry

Volumn 18, Issue 1, 2007, Pages 25-31

  Wang, Lei ^a   Wang, Hai Jun ^a   Dong, Wei Bo ^a   Ge, Qing Yu ^a   Lin, Li ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

Aromaticity; ASE; Five member planar electron systems; NICS

Indexed keywords

EID: 33846820401     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-006-9114-1     Document Type: Article

References (37)

1. Schleyer PVR, Freeman PK, Jiao H, Goldfuss B (1995) Angew Chem Int Ed Engl 34:337
2. Nyulászi L, Várnai P, Veszprémi T (1995) J Mol Struc (Theochem) 358:55
3. Cyrański MK, Krygowski TM, Schleyer PVR, Katritzky AR (2000) Chem Listy 94:788
4. Wang X, Hu HR, Tian AM, Wong NB, Chen SH, Li WK (2000) Chem Phys Lett 329:483
5. Delaere D, Dransfeld A, Nguyen MT, Vanquickenborne LG (2000) J Org Chem 65:2631
6. Chesnut DB, Bartolotti LJ (2000) Chem Phys 253:1
7. Zhang Y, Ma HY, Zeng FG, Dai BQ (2004) Chinese J Struct Chem 1:62
8. Schleyer PVR, Jiao H (1996) Pure Appl Chem 68:209
9. Cyrański MK, Krygowski TM, Katritzky AR, Schleyer PVR (2002) J Org Chem 67:1333
10. Cyrański MK, Schleyer PVR, Krygowski TM, Jiao H, Hohlneicher G (2003) Tetrahedron 59:1657
11. Cyrański MK (2005) Chem Rev 105:3773
12. Pauling LJ (1936) Chem Phys 4:673
13. London F (1937) J Phys Radium 8:397
14. Schleyer PVR, Maerker C, Dransfield A, Jiao H, van Eikema Hommes NJR (1996) J Am Chem Soc 118:6317
15. Hehre WJ, McIver RT, Pople JA, Schleyer PVR (1974) J Am Chem Soc 96:7162
16. Radom L (1974) J Chem Soc Chem Commun 10:403
17. George P, Trachtman M, Brett AM, Bock CW (1977) J Chem Soc Perkin Trans 2:1036
18. Katritzky AR, Karelson M, Sild S, Krygowski TM, Jug K (1998) J Org Chem 63:5228
19. Schleyer PVR, Jiao H, van Eikema Hommes NJR, Malkin VG, Malkina OL (1997) J Am Chem Soc 119:12669
20. Quinonero D, Garau C, Frontera A, Ballaster P, Costa A, Deya PM (2002) Chem Eur J 8:433
21. Cysewski P (2005) J Mol Struc (Theochem) 714:29
22. Schleyer PVR, Najafian K, Kiran B, Jiao H (2000) J Org Chem 65:426
23. Patchkovskii S, Thiel W (2000) J Mol Model 6:67
24. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven Jr, T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, 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, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, 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 I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh PA
25. Lazzeretti P, Tossell JA (1991) J Mol Struct (Theochem) 236:403
26. Cook MJ, Katritzky AR, Linda, P (1974) Aromaticity of heterocyclics. In Katritzky AR, Boulton AJ (eds), Advanced in heterocyclic chemistry, vol. 17, Academic Press, New York, p. 255
27. Raabe G, Michl (1985) J Chem Rev 85:419
28. Brook AG, Brook MA (1996) Adv Organomet Chem 39:71
29. Nyulaszi L (2001) Chem Rev 101:1229
30. (a) Nyulaszi L (1996) Inorg Chem 35:4690.
31. (b) Nyulaszi L (2000) Tetrahedron 56:79
32. Minkin VI, Glukhovtse MN, Smikin, BY (1994) Aromaticity and antiaromaticity, Studies in Electronic and Structural Aspects, Wiley, New York
33. Dransfeld A, Nyulaszi L, Schleyer PVR (1998) Inorg Chem 37:4413
34. Gimarc BM (1983) J Am Chem Soc 105:1979
35. Jiao H, Schleyer PVR (1998) J Phys Org Chem 11:655
36. Schleyer PVR, Kiran B, Simion DV, Sorensen TS (2000) J Am Chem Soc 122:510
37. McKee ML (2002) in Eaton GR, Wiley DC, Jardetzky O (eds.), Structures and mechanisms from ashes to enzymes, ACS Symposium Series, No. 827, American Chemical Society, Washington DC, p. 135