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Dehno Khalaji, A., Hafez Goran, S., Mehrani, S., Fejfarova, K., Dusek, M. (2017). New 16-membered macrocyclic Schiff base: Synthesis, structural and FT-IR studies. Iranian Chemical Communication, 5(Issue 2, pp. 121-236), 186-194.
Aliakbar Dehno Khalaji; Salar Hafez Goran; Sepideh Mehrani; Karla Fejfarova; Michal Dusek. "New 16-membered macrocyclic Schiff base: Synthesis, structural and FT-IR studies". Iranian Chemical Communication, 5, Issue 2, pp. 121-236, 2017, 186-194.
Dehno Khalaji, A., Hafez Goran, S., Mehrani, S., Fejfarova, K., Dusek, M. (2017). 'New 16-membered macrocyclic Schiff base: Synthesis, structural and FT-IR studies', Iranian Chemical Communication, 5(Issue 2, pp. 121-236), pp. 186-194.
Dehno Khalaji, A., Hafez Goran, S., Mehrani, S., Fejfarova, K., Dusek, M. New 16-membered macrocyclic Schiff base: Synthesis, structural and FT-IR studies. Iranian Chemical Communication, 2017; 5(Issue 2, pp. 121-236): 186-194.

New 16-membered macrocyclic Schiff base: Synthesis, structural and FT-IR studies

Article 8, Volume 5, Issue 2, pp. 121-236, Spring 2017, Page 186-194  XML PDF (842 K)
Document Type: Original Research Article
Authors
Aliakbar Dehno Khalaji 1; Salar Hafez Goran1; Sepideh Mehrani1; Karla Fejfarova2; Michal Dusek2
1Department of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran
2Institute of Physic of the Czech Academy of Sciences, Na Slovance 2, 182 21 Prague 8, Czech Republic
Abstract
In this paper, the structure of a new 16-membered macrocyclic Schiff base compound N,N′-(3,3′-dimethoxy-2,2′-(propane-1,3-diyldioxy)dibenzylidene)propane-1,3-diamine, C22H26N2O4 (1), derived from 1,3-propanediamine and 3,3′-dimethoxy-2,2′-(propane-1,3-diyldioxy)dibenzaldehyde has been studied by single crystal X-ray diffraction, DFT calculations at B3LYP/6-31G** and FT-IR spectroscopy. The title compound crystallizes in the monoclinic space group P21/n with unit cell parameters: a = 16.3273 (5) Å, b = 7.0832 (2) Å, c = 16.8586 (4) Ǻ, β = 93.135 (2)°, V = 1946.77 (9) Å3 and Z=4. The optimized molecular geometry agrees closely to that obtained from single crystal X-ray crystallography. The FT-IR spectrum (4000-400 cm-1) was recorded and compared with that of the calculated spectrum.

Graphical Abstract

New 16-membered macrocyclic Schiff base: Synthesis, structural and FT-IR studies
Keywords
Macrocyclic; Schiff base; single crystal; DFT calculations; monoclinic
Main Subjects
Organic chemistry
References
[1] P.A. Vigato, S. Tamburini, L. Bertolo, Coord. Chem. Rev., 2007, 251, 1311-1492.

[2] N.E. Borisova, M.D. Reshetova, Y.A. Ustynuk, Chem. Rev., 2007, 107, 46-79.

[3] D.R. Williams, Chem. Rev., 1972, 72, 203-213.

[4] D. Zhao, J.S. Moore, Chem. Commun., 2003, 807-818.

[5] G.W. Gokel, W.M. Leevy, M.E. Weber, Chem. Rev., 2004, 104, 2723-2750.

[6] J.L. Atwood, L.J. Barbour, M.J. Hardie, C.L. Raston, Coord. Chem. Rev., 2001, 222, 3-32.

[7] V. Prautzsch, S. Ibach, F. Vogtle, J. Inc. Phenom. Macrocycl. Chem., 1999, 33, 427-458.

[8] S. Ilhan, H. Temel, Trans. Met. Chem., 2007, 32, 1039-1046.

[9] S. Ilhan, H. Temel, R. Ziyadanogullari, M. Sekerci, Trans. Met. Chem., 2007, 32, 584-590.

[10] S. Ilhan, H. Temel, M. Sunkur, I. Tegin, Ind. J. Chem. A., 2008 , 47, 560-564.

[11] S. Ilhan, H. Temel, A. Kilic, E. Tas, Trans. Met. Chem., 2007, 32, 1012-1017.

[12] N.S. Al-Radadi, S.M. Al-Ashqar, M.M. Mostafa, J. Inc. Phenom. Macrocycl. Chem., 2011, 69, 157-165.

[13] H. Khanmohammadi, H. Keypour, M. Salehi Fard, M.H. Abnosi, J. Inc. Phenom. Macrocycl. Chem., 2009, 63, 97-108.

[14] A.A. Khandar, S.A. Hosseini-Yazdi, M. Khatamian, S.A. Zarei, Polyhedron, 2010, 29, 995-1000.

[15] I. Yilmaz, S. Ilhan, H. Temel, A. Kilic, J. Inc. Phenom. Macrocycl. Chem., 2009, 63, 163-169.

[16] N.E. Borisova, M.D. Reshetova, Y.A. Ustynuk, Chem. Rev., 2007, 107, 46-79.

[17] V. Reyes-Marquez, M. Sanchez, H. Hopfl, K.O. Lara, J. Inc. Phenom. Macrocycl. Chem., 2009, 65, 305-315.

[18] A.D. Khalaji, S. Hafez Ghoran, K. Gotoh, H. Ishida, Acta Crystallogr., 2011, E67, o2484.

[19] Gaussian 98, Revision A.3, M.J. Frisch, G.W. Trucks, H.B. Schlegel, F.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A.G Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi,V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng ,A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C.Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.

[20] L. Palatinus, G. Chapuis, J. Appl. Crystallogr., 2007, 40, 786.

[21] V. Petricek, M. Dusek, L. Palatinus, Jana2006. Structure determination software programs. Institute of Physics, Praha, Czech Republic, 2008.

[22] L.J. Farrugia, J. Appl. Crystallogr., 1997, 30, 656-658.

[23] S.F. Tayyari, M. Ghafari, M. Jamialahmadi, B. Chahkandi, B.O. Patrick, Y.A. Wang, J. Mol. Struct., 2013, 104, 20-28.

[24] R. Zhang, B. Du, G. Sun, Y. Sun, Spectrochim. Acta A., 2010, 75, 1115-1124.

[25] C.T. Zeyrek, N. Dilek, M. Yildiz, H. Ünver, Mol. Phys., 2014, 112, 2557-2574.

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