Abstract
The formation of benzotriazolaphane with carbonylbismethylene spacers in the reaction of 1,3-bis-(benzotriazolyl)propan-2-one with 1,3-dichloro-, 1,3-dibromo-, and 1,3-diiodopropan-2-ones has been simulated at the B3LYP/6-311G(d,p) level of theory. According to the calculations, the macrocyclic system can be formed only in the reaction of 1,3-bis(benzotriazolyl)propan-2-one with 1,3-diiodopropan-2-one due to additional stabilization of the macrocycle by triiodide ion.
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Boido, A., Boido, C.C., and Sparatore, F., Il Farmaco, 2001, vol. 56, p. 263.
Jones, L.F., O’Dea, L., Offermann, D.A., Jensen, P., Moubaraki, B., and Murray, K.S., Polyhedron, 2006, vol. 25, p. 360.
Lider, E.V., Potapov, A.S., Peresypkina, E.V., Smolentsev, A.I., Ikorskii, V.N., Khlebnikov, A.I., and Lavrenova, L.G., J. Struct. Chem., 2007, vol. 48, p. 500.
Zhou, J., Liu, X., Zhang, Y., Li, B., and Zhang, Y., Inorg. Chem. Commun., 2006, vol. 9, p. 216.
Meng, X., Song, Y., Hou, H., Fan, Y., Li, G., and Zhu, Y., Inorg. Chem., 2003, vol. 42, p. 1306.
Hou, H., Meng, X., Song, Y., Fan, Y., Zhu, Y., Lu, H., Du, C., and Shao, W., Inorg. Chem., 2002, vol. 41, p. 4068.
Meng, X., Li, U.J., Hou, H., Song, Y., Fan, Y., and Zhu, Y., J. Mol. Struct., 2008, vol. 891, p. 305.
Kokoszka, G.F., Baranowski, J., Goldstein, C., Orsini, J., Mighell, A.D., Himes, V.L., and Siedle, A.R., J. Am. Chem. Soc., 1983, vol. 105, p. 5627.
Reedijk, J., Siedle, A.R., Velapoldi, R.A., and Van Hest, J.A.M., Inorg. Chim. Acta., 1983, vol. 74, p. 109.
Børsting, P. and Steel, P.J., Eur. J. Inorg. Chem., 2004, no. 2, p. 376.
Yarosh, N.O., Zhilitskaya, L.V., Shagun, L.G., and Dorofeev, I.A., Russ. J. Org. Chem., 2014, vol. 50, p. 1384.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., 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., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J. Gaussian 09, Revision A.01, Wallingford CT: Gaussian, 2009.
Peng, C. and Schlegel, H.B., Isr. J. Chem., 1993, vol. 33, p. 449.
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Original Russian Text © V.A. Shagun, N.O. Yarosh, L.G. Shagun, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 10, pp. 1494–1498.
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Shagun, V.A., Yarosh, N.O. & Shagun, L.G. Quantum chemical study of the formation of cyclophane structure in the alkylation of 1,3-bis(benzotriazolyl)-propan-2-one with 1,3-dihalopropan-2-ones. Russ J Org Chem 51, 1464–1468 (2015). https://doi.org/10.1134/S107042801510019X
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DOI: https://doi.org/10.1134/S107042801510019X