Structural properties and 13C chemical shifts of bis- and tris(2-thienyl)methinium and related cations: A combined theoretical and experimental study

Journal of Physical Organic Chemistry

Volumn 16, Issue 1, 2003, Pages 53-62

  Fabian, Jürgen ^a   Hartmann, Horst ^b   Noack, Antje ^b  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b University of Applied Sciences Merseburg   (Germany)

Author keywords

13C NMR chemical shifts; Molecular structure; Quantum chemical calculations; Tris(2 thienyl)methinium ions; UV VIS spectral data

Indexed keywords

CARBON; MOLECULAR STRUCTURE; POSITIVE IONS; PROBABILITY DENSITY FUNCTION;

CHEMICAL SHIFTS;

AROMATIC COMPOUNDS;

EID: 0037234007     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.573     Document Type: Article

References (41)

1. Noack A, Schröder A, Hartmann H. Angew. Chem. 2001; 113: 3097-3100; Angew. Chem., Int. Ed. Engl. 2001; 40: 3008-3011.
2. Noack A, Schröder A, Hartmann H. Angew. Chem. 2001; 113: 3097-3100; Angew. Chem., Int. Ed. Engl. 2001; 40: 3008-3011.
3. Fabian J, Hartmann H. Light Absorption of Organic Colorants. Springer: Berlin, 1990, and references cited therein.
4. Vares T, Medio-Simon M, Abarca B, Ballesteros R, Asensio G, Garcia-Grande S, Perez-Carreno E, Gomez-Beltran F. J. Chem. Soc., Chem. Commun. 1993; 1476-1478.
5. Gomes de Mesquita AH, MacGillavry GH, Eriks K. Acta Crystallogy. 1965; 18: 437-443; Lovell S, Marquardt BJ, Kahr B. J. Chem. Soc., Perkin Trans 2 1999; 2241-2247; Spangler BD, Vanýsek P, Hernandez LC, Rogers RD. J. Crystallogy. Spectrosc. Res. 1989; 19: 589-596; Sundaralingam M, Chwang AK. In Carbonium Ions, vol. 5, Olah GA, Schleyer PR (eds). Wiley: New York, 1976; Chapt. 39, 2427-2476.
6. Gomes de Mesquita AH, MacGillavry GH, Eriks K. Acta Crystallogy. 1965; 18: 437-443; Lovell S, Marquardt BJ, Kahr B. J. Chem. Soc., Perkin Trans 2 1999; 2241-2247; Spangler BD, Vanýsek P, Hernandez LC, Rogers RD. J. Crystallogy. Spectrosc. Res. 1989; 19: 589-596; Sundaralingam M, Chwang AK. In Carbonium Ions, vol. 5, Olah GA, Schleyer PR (eds). Wiley: New York, 1976; Chapt. 39, 2427-2476.
7. Gomes de Mesquita AH, MacGillavry GH, Eriks K. Acta Crystallogy. 1965; 18: 437-443; Lovell S, Marquardt BJ, Kahr B. J. Chem. Soc., Perkin Trans 2 1999; 2241-2247; Spangler BD, Vanýsek P, Hernandez LC, Rogers RD. J. Crystallogy. Spectrosc. Res. 1989; 19: 589-596; Sundaralingam M, Chwang AK. In Carbonium Ions, vol. 5, Olah GA, Schleyer PR (eds). Wiley: New York, 1976; Chapt. 39, 2427-2476.
8. Gomes de Mesquita AH, MacGillavry GH, Eriks K. Acta Crystallogy. 1965; 18: 437-443; Lovell S, Marquardt BJ, Kahr B. J. Chem. Soc., Perkin Trans 2 1999; 2241-2247; Spangler BD, Vanýsek P, Hernandez LC, Rogers RD. J. Crystallogy. Spectrosc. Res. 1989; 19: 589-596; Sundaralingam M, Chwang AK. In Carbonium Ions, vol. 5, Olah GA, Schleyer PR (eds). Wiley: New York, 1976; Chapt. 39, 2427-2476.
9. Lueck HB, MCHale JL, Edwards WD. J. Am. Chem. Soc. 1992; 114: 2342-2348.
10. Koch W, Holthausen MC. A Chemist's Guide to Density Functional Theory. Wiley-VCH: Weinheim, 2000, and references cited therein.
11. Becke AD. J. Chem. Phys. 1993; 98: 1372-1377; 5648-5652.
12. Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785-789.
13. Perdew JP. Phys. Rev. B 1986; 33: 8822-8824.
14. Chesnut DP. In Reviews in Computational Chemistry, vol. 8, Lipkowitz KB, Boyd DB (eds). Wiley-VCH: New York, 1996; 245-297, and references cited therein.
15. Cheeseman JR, Tracks GW, Keith TA, Frisch MJ. J. Chem. Phys. 1996; 104: 5497-5509.
16. Bartlett RJ, Stanton JF. In Reviews in Computational Chemistry, vol. 5, Lipkowitz KB, Boyd DB (eds). Wiley-VCH: New York, 1994; 65-169, and references cited therein.
17. Reed AE, Weinstock RB, Weinhold F. J. Chem. Phys. 1985; 83: 735-746; Reed AE, Curtiss IA, Weinhold F. Chem. Rev. 1988; 88: 899-926.
18. Reed AE, Weinstock RB, Weinhold F. J. Chem. Phys. 1985; 83: 735-746; Reed AE, Curtiss IA, Weinhold F. Chem. Rev. 1988; 88: 899-926.
19. Ridley J, Zerner MC. Theor. Chem. Acta 1973; 32: 111-134; Zerner MC. In Review in Computational Chemistry, vol. 2, Lipkowitz KB, Boyd DB (eds). Wiley-VCH: New York, 1991; 313-365, and references cited therein.
20. Ridley J, Zerner MC. Theor. Chem. Acta 1973; 32: 111-134; Zerner MC. In Review in Computational Chemistry, vol. 2, Lipkowitz KB, Boyd DB (eds). Wiley-VCH: New York, 1991; 313-365, and references cited therein.
21. Fabian J. Theor. Chem. Acc. 2001; 106: 199-217.
22. Merchán M, Serrano-Andrés L, Fülscher MP, Roos BO. In Recent Advances in Multireference Theory, vol. 4, Hirao K (ed). World Scientific: Singapore, 1999; 161-195.
23. Casida ME. In Recent Developments and Applications of Modern Density Functional Theory, vol. 4, Seminario JM (ed). Elsevier: Amsterdam, 1996; 391-439.
24. 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, 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, 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.7. Gaussian: Pittsburgh, PA, 1998.
25. Ma B, Li J-H, Schaeffer HF III, Allinger NL. J. Phys. Chem. 1996; 100: 8763-8769; Fabian J, Hess BA Jr. J. Org. Chem. 1997; 62: 1766-1774.
26. Ma B, Li J-H, Schaeffer HF III, Allinger NL. J. Phys. Chem. 1996; 100: 8763-8769; Fabian J, Hess BA Jr. J. Org. Chem. 1997; 62: 1766-1774.
27. Hargittai I. The Structure of Volatile Sulphur Compounds. Akadémiai Kiadó: Budapest, 1985.
28. Altmann JA, Handy NC, Ingamells EE. Mol. Phys. 1997; 92: 339-352; Liu R, Zhou Y, Kasmai H. Spectrochim. Acta, Part A 1997; 53: 1241-1256; Pou-Amérigo R, Viruela PM, Rubio M, Ortí E.Chem. Phys Lett. 2002; 352: 491-498.
29. Altmann JA, Handy NC, Ingamells EE. Mol. Phys. 1997; 92: 339-352; Liu R, Zhou Y, Kasmai H. Spectrochim. Acta, Part A 1997; 53: 1241-1256; Pou-Amérigo R, Viruela PM, Rubio M, Ortí E.Chem. Phys Lett. 2002; 352: 491-498.
30. Altmann JA, Handy NC, Ingamells EE. Mol. Phys. 1997; 92: 339-352; Liu R, Zhou Y, Kasmai H. Spectrochim. Acta, Part A 1997; 53: 1241-1256; Pou-Amérigo R, Viruela PM, Rubio M, Ortí E. Chem. Phys Lett. 2002; 352: 491-498.
31. Karpfen A, Choi CH, Kertesz M. J. Phys. Chem. A 1997; 101: 7426-7433.
32. Abarca B, Ascensio G, Ballesteros R, Luna C. Tetrahedron Lett. 1986; 27: 5657-5660.
33. Dähne S. Z. Chem. 1965; 5: 441-451; Dähne S, Kulpe S. In Abhandlungen der Akademie der Wissenschaften der DDR. Akademie-Verlag: Berlin, 1977; No. 8; Dähne S, Moldenhauer F. Prog. Phys. Org. Chem. 1985; 15: 1-130.
34. Dähne S. Z. Chem. 1965; 5: 441-451; Dähne S, Kulpe S. In Abhandlungen der Akademie der Wissenschaften der DDR. Akademie-Verlag: Berlin, 1977; No. 8; Dähne S, Moldenhauer F. Prog. Phys. Org. Chem. 1985; 15: 1-130.
35. Dähne S. Z. Chem. 1965; 5: 441-451; Dähne S, Kulpe S. In Abhandlungen der Akademie der Wissenschaften der DDR. Akademie-Verlag: Berlin, 1977; No. 8; Dähne S, Moldenhauer F. Prog. Phys. Org. Chem. 1985; 15: 1-130.
36. Sieber S, Buzek P, Rague von Schleyer P, Koch W, de M. Carneiro JW. J. Am. Chem. Soc. 1993; 115: 259-270.
37. Spiesecke H, Schneider WG. Tetrahedron Lett. 1961; 468-472; Olah GA, Mateesen GD. J. Am. Chem. Soc. 1970; 92: 1430-1432.
38. Spiesecke H, Schneider WG. Tetrahedron Lett. 1961; 468-472; Olah GA, Mateesen GD. J. Am. Chem. Soc. 1970; 92: 1430-1432.
39. Suzuki H. Electronic Absorption Spectra and Geometry of Organic Molecules. Academic Press: New York, 1967.
40. Fabian J, Mehlhorn A, Zahradník R. J. Phys. Chem. 1968; 72: 3975-3985.; Hartmann H, Fabian J. Ber. Bunsenges. Phys. Chem. 1969; 73: 107-110.
41. Fabian J, Mehlhorn A, Zahradník R. J. Phys. Chem. 1968; 72: 3975-3985.; Hartmann H, Fabian J. Ber. Bunsenges. Phys. Chem. 1969; 73: 107-110.