Vibrational spectroscopic and Hirshfeld surface analysis of N,N'-(azanediylbis(2,1-phenylene))bis(2-chloropropanamide)

Aysegul Suzan Polat; Ilkay Gumus; Hakan Arslan

doi:10.5155/eurjchem.10.4.386-402.1921

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Published: Dec 31, 2019

DOI: https://doi.org/10.5155/eurjchem.10.4.386-402.1921

Keywords:

Vibration spectrum, Ab initio calculations, Infrared spectroscopy, Redox active compound, Density functional theory, Hirshfeld surface analysis

Section

Research Article

Issue

Vol. 10 No. 4 (2019): December 2019

Dates

Received 2019-09-02
Accepted 2019-10-26
Published 2019-12-31

Aysegul Suzan Polat

Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey

http://orcid.org/0000-0002-0281-4011

Ilkay Gumus

Department of Basic Sciences, Faculty of Maritime, Mersin University, Mersin, 33343, Turkey

http://orcid.org/0000-0002-9398-0057

Hakan Arslan

Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey

http://orcid.org/0000-0003-0046-9442

Abstract

The title molecule, N,N'-(azanediylbis(2,1-phenylene))bis(2-chloropropanamide) (L^NNN) was synthesized and characterized by means of Hirshfeld surface analysis and vibrational (FT-IR and RAMAN) studies. Ab-initio Hartree-Fock (HF) and density functional theory (DFT; BLYP, B3LYP, B3PW91 and mPW1PW91) calculations were accomplished using 6-31G(d,p) and 6-311G(d,p) basis sets. The comparison of calculated bond lengths and angles with X-ray crystal structure shows sufficient agreement. The solid phase FT-IR and FT-RAMAN spectra of L^NNN have been recorded in the regions 4000-525 cm^-1and 4000-50 cm^-1, respectively. A comparative analysis between the calculated and experimental vibrational frequencies was carried out and significant bands were assigned. The results indicated a good correlation between experimental and theoretical IR and RAMAN frequencies. A detailed analysis of the intermolecular interactions via Hirshfeld surface analysis and fingerprint plots revealed that supramolecular structure of the L^NNN is stabilized mainly by the formation of H···H, C···H, Cl···H ve O···H intermolecular interactions.

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Polat, A. S.; Gumus, I.; Arslan, H. Vibrational Spectroscopic and Hirshfeld Surface Analysis of N,N’-(azanediylbis(2,1-phenylene) bis(2-Chloropropanamide). Eur. J. Chem. 2019, 10, 386-402.

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References

[1]. Lyaskovskyy, V.; Bruin, B. Am. Chem. Soc. Catal. 2012, 2, 270-279.
https://doi.org/10.1021/cs200660v

[2]. Allgeier, A. M.; Mirkin, C. A. Angew. Chem., Int. Edit. 1998 37, 894-908.
https://doi.org/10.1002/(SICI)1521-3773(19980420)37:7<894::AID-ANIE894>3.3.CO;2-C

[3]. Wile, B. M.; Trovitch, R. J.; Bart, S. C.; Tondreau, A. M.; Lobkovsky, E.; Milsmann, C.; Bill, E.; Wieghardt, K.; Chirik, P. J. Inorg. Chem. 2009, 48(9), 4190-4200.
https://doi.org/10.1021/ic801623m

[4]. Bart, S. C.; Lobkovsky, E.; Bill, E.; Chirik; P. J. J. Am. Chem. Soc. 2006, 128(16), 5302-5303.
https://doi.org/10.1021/ja057165y

[5]. Tondreau, A. M.; Milsmann, C.; Patrick, A. D.; Hoyt, H. M.; Lobkovsky, E.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2010, 132(42), 15046-15059.
https://doi.org/10.1021/ja106575b

[6]. Skabara, P. J.; Pozo-Gonzalo, C.; Lardies, M. N.; Laguna, M.; Cerrada, E.; Luquin, A.; Gonzalez, B.; Coles, S. J.; Hursthouse, M. B.; Harrington, R. W.; Clegg, W. Dalton Trans. 2008, 23, 3070-3079.
https://doi.org/10.1039/b801187g

[7]. Mukherjee, C.; Pieper, U.; Bothe, E.; Bachler, V.; Bill, E.; Weyhermuller, T.; Chaudhuri, P. Inorg. Chem. 2008, 47(19), 8943-8956.
https://doi.org/10.1021/ic8009767

[8]. Zhu, D.; Thapa, I.; Korobkov, I.; Gambarotta, S.; Budzelaar, P. H. M. Inorg. Chem. 2011, 50, 9879-9887.
https://doi.org/10.1021/ic2002145

[9]. Dzik, W. I.; Van Der Vlugt, J. I.; Reek, J. N. H.; De Bruin, B. Angew. Chem., Int. Ed. 2011, 50, 3356-3358.
https://doi.org/10.1002/anie.201006778

[10]. Hindson, K.; De Bruin, B. Eur. J. Inorg. Chem. 2012, 3, 340-580.
https://doi.org/10.1002/ejic.v2012.3

[11]. Kaim, W. Coord. Chem. Rev. 1987, 76, 187-235.
https://doi.org/10.1016/0010-8545(87)85004-X

[12]. Chirik, P.J. Inorg. Chem. 2011, 50(20), 9737-9914.
https://doi.org/10.1021/ic201881k

[13]. Van der Vlugt, J. I., Eur. J. Inorg. Chem. 2012, 3, 363-375.
https://doi.org/10.1002/ejic.201100752

[14]. Dzik, W. I.; Zhang, P. X.; de Bruin, B. Inorg. Chem. 2011, 50(20), 9896-9903.
https://doi.org/10.1021/ic200043a

[15]. Kaim, W. Coord. Chem. Rev. 2010, 254, 1580-1588.
https://doi.org/10.1016/j.ccr.2010.01.009

[16]. Nawn, G.; Waldie, K. M.; Oakley, S. R.; Peters, B. D.; Mandel, D.; Patrick, B. P.; McDonald, R.; Hicks, R. G. Inorg. Chem. 2011, 50, 9826-9837.
https://doi.org/10.1021/ic200388y

[17]. Bowman, A. C.; Milsmann, C.; Hojilla, A. C. C.; Lobkovsky, E.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2010, 132(5), 1676-1684.
https://doi.org/10.1021/ja908955t

[18]. Bowman, C. A.; Milsmann, C.; Bill, E.; Lobkovsky, E.; Weyhermüller, T.; Wieghardt, K.; Chirik, P. J. Inorg. Chem. 2010, 49(13), 6110-6123.
https://doi.org/10.1021/ic100717w

[19]. Manuel, T. D.; Rohde, J. U. Am. Chem. Soc. 2009, 131(43), 15582-15583.
https://doi.org/10.1021/ja9065943

[20]. Rolle, C. J.; Hardcastle, K. I.; Soper, J. D. Inorg. Chem. 2008, 47(6), 1892-1894.
https://doi.org/10.1021/ic702390q

[21]. Vlcek, A. Coord. Chem. Rev. 2010, 254(13-14), 1357-1357.
https://doi.org/10.1016/j.ccr.2010.01.015

[22]. Ward, M. D.; McCleverty, J. A. J. Chem. Soc. Dalton Trans. 2002, 3, 275-288.
https://doi.org/10.1039/b110131p

[23]. Smith, A. L.; Hardcastle, K. I.; Soper, J. D. J. Am. Chem. Soc. 2010, 132, 14358-14360.
https://doi.org/10.1021/ja106212w

[24]. Arslan, H. Ligand design studies for metal catalyzed oxidation reactions, TUBITAK Project no: 112T322, 2012.

[25]. Polat, A. S., MSc Thesis, Mersin University, Mersin, Turkey, 2019.

[26]. Polat, A. S.; Gumus, I.; Arslan, H. Int. Eng. Nat. Sci. Conf. Book, Diyarbakir, Turkey, 2019.

[27]. Aydogdu, S. I., MSc Thesis, Mersin University, Mersin, Turkey, 2019.

[28]. Aydogdu, I.; Gumus, I.; Arslan, H. Int. Eng. Nat. Sci. Conf. Book, Diyarbakir, Turkey, 2019.

[29]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A. V.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery, J. A.; Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Keith, T. A.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J. Gaussian 16, Revision C.01, Gaussian, Inc.; Wallingford CT, 2016.

[30]. Dennington, R.; Keith, T. A.; Millam, J. M. GaussView, Version 6, Semichem Inc.; Shawnee Mission, KS, 2016.

[31]. Moller, C.; Plesset, M.S. Phys. Rev. 1934, 46(7), 618-622.
https://doi.org/10.1103/PhysRev.46.618

[32]. Becke, A.D. J. Chem. Phys. 1993, 98(7), 5648-5652.
https://doi.org/10.1063/1.464913

[33]. Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1988, 37(2), 785-789.
https://doi.org/10.1103/PhysRevB.37.785

[34]. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108(2), 664-675.
https://doi.org/10.1063/1.475428

[35]. Burke, K.; Perdew, J.P.; Wang, Y.; Dobson, J.F.; Vignale, G. M.P. Das (Eds.), Electronic Density Functional Theory: Recent Progress and New Directions, Plenum Press, New York, 1998.

[36]. Predew, J.P.; Wang, Y. Phys. Rev. B 1992, 45(23), 13244-13249.
https://doi.org/10.1103/PhysRevB.45.13244

[37]. Foresman, B.; Frisch, E. Exploring Chemistry with Electronic Structure Methods: a Guide to Using Gaussian, Gaussian Pitttsburg, PA, 1993.

[38]. Scott, A. P.; Radom, L. J. Chem. 1996, 100, 16502-16513.
https://doi.org/10.1021/jp960976r

[39]. Arslan, H.; Algul, O.; Dundar, Y. Vib. Spectrosc. 2007, 44, 248-255
https://doi.org/10.1016/j.vibspec.2006.12.003

[40]. Arslan, H.; Algul, O. Spectrochim. Acta A 2008, 70, 109-116
https://doi.org/10.1016/j.saa.2007.07.027

[41]. Yabalak, E.; Gunay, F.; Kasumov, V.; Arslan, H. Spectrochim. Acta A 2013, 110, 291-303
https://doi.org/10.1016/j.saa.2013.03.003

[42]. Arslan, H.; Mansuroglu, D.; Vanderveer, D.; Binzet, G. Spectrochim. Acta A 2009, 72, 561-571.
https://doi.org/10.1016/j.saa.2008.10.049

[43]. Arslan, H.; Demircan, A. Int. J. Mol. Sci. 2007, 8, 1064-1082.
https://doi.org/10.3390/i8111064

[44]. Arslan, H.; Floerke, U.; Kulcu, N.; Binzet, G. Spectrochim. Acta A 2007, 68, 1347-1355.
https://doi.org/10.1016/j.saa.2007.02.015

[45]. Panchenko, Y. N. J. Mol. Struct. 2001, 567-568, 217-230.
https://doi.org/10.1016/S0022-2860(01)00555-5

[46]. Rauhut, G.; Pulay, P. J. Phys. Chem. 1995, 99(10), 3093-3100.
https://doi.org/10.1021/j100010a019

[47]. Arslan, H. Performance Analysis of Vibrational Frequencies, 1.0, Mersin, Turkey, 2007.

[48]. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88(6), 899-926.
https://doi.org/10.1021/cr00088a005

[49]. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. J. Am. Chem. Soc. 1998, 120(46), 12051-12068.
https://doi.org/10.1021/ja980917m

[50]. Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer17, University of Western Australia, http://hirshfeldsurface.net, 2017.

[51]. Socrates, G. Infrared and Raman Characteristic Group Frequencies, John Wiley & Sons Ltd. Chichester, 2001.

[52]. Silverstein, R.M.; Webster, F.X.; Kiemle, D.J.; Bryce, D.J. Spectrometric Identification of Organic Compounds, Wiley, 2014.

[53]. Colt, N. B.; Daly, L. H.; Wiberly S. E. Introduction to Infrared and Raman Spectroscopy, 3th edition, Academic Press, Boston, 1990.

[54]. Lebas, J. M.; Garrigou-Lagrange, C.; Josien, M. L. Spectrochim. Acta 1959, 15, 225-235.
https://doi.org/10.1016/S0371-1951(59)80311-8

[55]. Wiberley, S. E.; Bunce, S. C.; Bauner, W. H. Anal. Chem. 1960, 32, 217-221.
https://doi.org/10.1021/ac60158a025

[56]. Linvien, D.; Cothup, N.B.; Fateley, W.G.; Graselli, J.G., The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, Academic Press, Boston, 1991.

[57]. Beaula, T. J.; Joe, I. H.; Rastogi, V. K.; Jothy, V. B. Chem. Phys. Lett. 2015, 624, 93-101.
https://doi.org/10.1016/j.cplett.2015.02.026

[58]. Abraham, C. S.; Prasana, J. C.; Muthu, S. Spectrochim. Acta Mol. Biomol Spectrosc. 2017, 181, 153-163.
https://doi.org/10.1016/j.saa.2017.03.045

[59]. Mulliken, R.S. J. Chem. Phys. 1955, 23, 1833-1840.
https://doi.org/10.1063/1.1740588

[60]. Wang, J. W.; Zhang, Y. W.; Wang, M. X.; Luo, Y. H.; Sun, B. W. Polyhedron 2017, 124, 243-250.
https://doi.org/10.1016/j.poly.2016.12.045

[61]. Spackman, M. A.; Jayatilaka, D. Cryst. Eng. Commun. 2009, 11, 19-32.
https://doi.org/10.1039/B818330A

Supporting Agencies

This study was supported by Research Fund of Mersin University in Turkey with Project Number, 2018-1-TP2-2800.

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