Collect. Czech. Chem. Commun. 2005, 70, 559-578
https://doi.org/10.1135/cccc20050559

Electronic Spectra of Conjugated Polyynes, Cumulenes and Related Systems: A Theoretical Study

Rudolf Zahradníka, Martin Srneca and Zdeněk Havlasb,*

a J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejškova 3, 182 23 Prague 8, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

References

1. Pople J. A.: Trans. Faraday Soc. 1953, 49, 1375. <https://doi.org/10.1039/tf9534901375>
2a. Pariser R., Parr R. G.: J. Chem. Phys. 1953, 21, 466. <https://doi.org/10.1063/1.1698929>
2b. Pariser R., Parr R. G.: J. Chem. Phys. 1953, 21, 767. <https://doi.org/10.1063/1.1699030>
3a. Roos B. O., Anderson K., Fülscher M. P., Malquist P., Serrano-Andres L., Pierloot K., Merchan M.: Adv. Chem. Phys. 1996, 63, 219. <https://doi.org/10.1002/9780470141526.ch5>
3b. Murphy R. B., Messmer R. P.: Chem. Phys. Lett. 1991, 183, 443. <https://doi.org/10.1016/0009-2614(91)90407-Z>
3c. Murphy R. B., Messmer R. P.: J. Chem. Phys. 1992, 97, 4170. <https://doi.org/10.1063/1.463992>
4a. Bauernschmitt R., Häser M., Treutler O., Ahlrichs R.: Chem. Phys. Lett. 1997, 264, 573. <https://doi.org/10.1016/S0009-2614(96)01343-7>
4b. Tozer D. J., Handy N. C.: J. Chem. Phys. 1998, 109, 10180. <https://doi.org/10.1063/1.477711>
4c. Hirata S., Lee T. J., Head-Gordon M.: J. Chem. Phys. 1999, 111, 8904. <https://doi.org/10.1063/1.480235>
4d. Sobolewski A. L., Domcke W.: Phys. Chem. Chem. Phys. 1999, 1, 3065. <https://doi.org/10.1039/a902565k>
4e. Tozer D. J., Amos R. D., Handy N. C., Roos B. O., Serrano-Andrés L.: Mol. Phys. 1999, 97, 859. <https://doi.org/10.1080/00268979909482888>
5a. Van Caillie C., Amos R. D.: Chem. Phys. Lett. 1999, 308, 249. <https://doi.org/10.1016/S0009-2614(99)00646-6>
5b. Van Caillie C., Amos R. D.: Chem. Phys. Lett. 2000, 317, 159. <https://doi.org/10.1016/S0009-2614(99)01346-9>
5c. Amos R. D.: Chem. Phys. Lett. 2002, 364, 612. <https://doi.org/10.1016/S0009-2614(02)01349-0>
5d. Furche F., Ahlrichs R.: J. Chem. Phys. 2002, 117, 7433. <https://doi.org/10.1063/1.1508368>
5e. Hutter J.: J. Chem. Phys. 2003, 118, 3928. <https://doi.org/10.1063/1.1540109>
6a. Parac M., Grimme S.: J. Phys. Chem. A 2002, 106, 6844. <https://doi.org/10.1021/jp020550e>
6b. Grimme S., Parac M.: ChemPhysChem 2003, 292. <https://doi.org/10.1002/cphc.200390047>
7. Christiansen O., Koch H., Jorgensen P.: Chem. Phys. Lett. 1995, 243, 409. <https://doi.org/10.1016/0009-2614(95)00841-Q>
8. Botschwina P.: Phys. Chem. Chem. Phys. 2003, 5, 3337. <https://doi.org/10.1039/b303753n>
9a. Grutter M., Wyss M., Fulara J., Maier J. P.: J. Phys. Chem. A 1998, 102, 9785. <https://doi.org/10.1021/jp983185t>
9b. Grutter M., Wyss M., Maier J. P.: J. Chem. Phys. 1999, 110, 1492. <https://doi.org/10.1063/1.478022>
9c. Grutter M., Wyss M., Riaplov E., Maier J. P., Peyerimhoff S. D., Hanrath M.: J. Chem. Phys. 1999, 111, 7397. <https://doi.org/10.1063/1.480062>
9d. Kirkwood D. A., Tulej M., Pachkov M. V., Schnaiter M., Güthe F., Grutter M., Wyss M., Maier J. P., Fischer G.: J. Chem. Phys. 1999, 111, 9280. <https://doi.org/10.1063/1.479842>
9e. Sinclair W. E., Pfluger D., Maier J. P.: J. Chem. Phys. 1999, 111, 9600. <https://doi.org/10.1063/1.480293>
9f. Sinclair W. E., Pfluger D., Verdes D., Maier J. P.: J. Chem. Phys. 2000, 112, 8899. <https://doi.org/10.1063/1.481503>
9g. Vaizert O., Motylewski T., Wyss M., Riaplov E., Linnartz H., Maier J. P.: J. Chem. Phys. 2001, 114, 7918. <https://doi.org/10.1063/1.1361254>
9h. Ding H., Pino T., Güthe F., Maier J. P.: J. Chem. Phys. 2002, 117, 8362. <https://doi.org/10.1063/1.1511183>
9i. Ding H., Pino T., Güthe F., Maier J. P.: J. Chem. Phys. 2002, 117, 8362. <https://doi.org/10.1063/1.1511183>
9j. Ding H., Schmidt T. W., Pino T., Boguslavskiy A. E., Güthe F., Maier J. P.: J. Chem. Phys. 2003, 119, 814. <https://doi.org/10.1063/1.1578476>
9k. Ding H., Schmidt T. W., Pino T., Güthe F., Maier J. P.: Phys. Chem. Chem. Phys. 2003, 5, 4772. <https://doi.org/10.1039/b309100g>
9l. Pino T., Ding H., Güthe F., Maier J. P.: J. Chem. Phys. 2001, 114, 2208. <https://doi.org/10.1063/1.1338530>
10. Zhang C., Cao Z., Wu H., Zhang Q.: Int. J. Quantum Chem. 2003, 98, 299. <https://doi.org/10.1002/qua.20023>
11. Zahradník R., Šroubková L.: Helv. Chim. Acta 2003, 86, 979. <https://doi.org/10.1002/hlca.200390115>
12a. Zahradník R., Šroubková L.: Isr. J. Chem. 2003, 43, 243. <https://doi.org/10.1560/KJPV-MPGQ-NVVX-252K>
12b. Zahradník R., Šroubková L.: Int. J. Quantum Chem., in press.
13. Nakatsuji H., Hirao K.: J. Chem. Phys. 1978, 68, 2053. <https://doi.org/10.1063/1.436028>
14. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, Jr., J. A., Vreven, T., Kudin, K. N., Burant, J. C. , Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., 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, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J. A.: Gaussian 03, Revision B.02, Gaussian, Inc., Wallingford CT, 2004.
15. Handy N. C., Tozer D. J.: J. Comput. Chem. 1999, 20, 106. <https://doi.org/10.1002/(SICI)1096-987X(19990115)20:1<106::AID-JCC11>3.0.CO;2-P>
16. Adamo C., Barone V.: Chem. Phys. Lett. 1999, 314, 152. <https://doi.org/10.1016/S0009-2614(99)01113-6>
17. Duning T. H., Jr.: J. Chem. Phys. 1989, 90, 1007. <https://doi.org/10.1063/1.456153>
18a. Kloster-Jensen E.: Angew. Chem., Int. Ed. Engl. 1972, 11, 438. <https://doi.org/10.1002/anie.197204381>
18b. Kloster-Jensen E., Haink H.-J., Christen H.: Helv. Chim. Acta 1974, 57, 1731. <https://doi.org/10.1002/hlca.19740570625>
18c. Eastmond R., Johnson T. R., Walton D. R. M.: Tetrahedron 1972, 28, 4601. <https://doi.org/10.1016/0040-4020(72)80041-3>
19a. Bohlmann F., Bornowski H., Arndt C.: Fortschr. Chem. Forsch. 1963, 4, 138. <https://doi.org/10.1007/BFb0051920>
19b. UV Atlas of Organic Compounds, Vol. V. Butterworths and Verlag Chemie, London 1966.
19c. Eastmond R., Walton D. R. M.: Tetrahedron 1972, 28, 4591. <https://doi.org/10.1016/0040-4020(72)80040-1>
19d. Schermann G., Grösser T., Hampel F., Hirsch A.: Chem. Eur. J. 1997, 3, 1105. <https://doi.org/10.1002/chem.19970030718>
20. Ventura E., Dallos M., Lischka H.: J. Chem. Phys. 2003, 118, 1702. <https://doi.org/10.1063/1.1532312>
21. Herzberg G.: Molecular Spectra and Molecular Structure, Vol. III. Van Nostrand Reinhold Comp., New York 1966.
22. Dressler R., Allen M.: J. Chem. Phys. 1987, 87, 4510. <https://doi.org/10.1063/1.452864>
23. Lewis G. N., Calvin M.: Chem. Rev. 1939, 26, 237.
24. Mehlhorn A.: J. Prakt. Chem. 1986, 328, 784. <https://doi.org/10.1002/prac.19863280518>
25. Horný Ľ., Petraco N. D. K., Pak Ch., Schaefer H. F., III: J. Am. Chem. Soc. 2002, 124, 5861. <https://doi.org/10.1021/ja012014q>
26a. Bohlmann F., Kieslich K.: Chem. Ber. 1954, 87, 1363. <https://doi.org/10.1002/cber.19540870926>
26b. Fischer H. in: The Chemistry of Alkenes (S. Patai, Ed.), p. 1025. Interscience, London 1964.
27a. Hsu Ch.-P., Hirata S., Head-Gordon M.: J. Phys. Chem. A 2001, 105, 451. <https://doi.org/10.1021/jp0024367>
27b. Rijkenberg A., Bebelaar D., Buma W. J.: J. Am. Chem. Soc. 2000, 122, 7418. <https://doi.org/10.1021/ja000864k>
27c. Serrano-Andrés L., Merchán M., Nebot-Gil I., Lindh R., Roos B. O.: J. Chem. Phys. 1993, 98, 3151. <https://doi.org/10.1063/1.465071>
27d. Hünig S., Quast H.: 2. Internationale Farbensymposium – Optische Anregung organischer Systeme. Neuere farbige Systeme, Symp. Publ. House, Schloss Elman 1964, p. 184. e) Matsen F. A., Becker R. S., Scott D. R. in: Chemical Applications of Spectroscopy, Part I. Wiley-Interscience, New York 1968.
27f. Murrell J. N.: The Theory of the Electronic Spectra of Organic Molecules. Methuen, London 1963.
27g. Zahradník R., Čársky P.: J. Phys. Chem. 1970, 74, 1240. <https://doi.org/10.1021/j100701a014>