European Journal of Chemistry

Hirshfeld surface and theoretical studies of 2,2,2-trichloro-N,N-bis(2-(2,2,2-trichloroacetamido)phenyl)acetamide compound

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Immihan Sezen Aydogdu
Ilkay Gumus
Hakan Arslan

Abstract

The vibrational frequencies, atomic charges and the related properties of the 2,2,2-trichloro-N,N-bis(2-(2,2,2-trichloroacetamido)phenyl)acetamide (H2LNNN) were investi-gated by Ab-initio Hartree-Fock (HF) and Density Functional Theory (DFT) methods such as BLYP, B3LYP, B3PW91 and mPW1PW91 functionals with 6-31G(d,p) and 6-311G(d,p) basis sets. The experimentally determined parameters were compared with those calculated theoretically and they were found to complement each other with a very good correlation. The theoretical vibrational spectrum of H2LNNN molecule was interpreted by means of potential energy distributions using the SQM 2.0 program. The Hirshfeld surface analysis was carried out to discuss the role of the hydrogen bonds and other intermolecular contacts in crystal lattice. Hirshfeld surface analysis revealed the occurrence of Cl⋯H, Cl⋯Cl, Cl⋯C, H···H, O⋯H, C···H and Cl···π interactions that display an important role on the crystal packing stabilization of the compound.


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Aydogdu, I. S.; Gumus, I.; Arslan, H. Hirshfeld Surface and Theoretical Studies of 2,2,2-Trichloro-N,N-bis(2-(2,2,2-trichloroacetamido)phenyl)acetamide Compound. Eur. J. Chem. 2019, 10, 323-335.

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References

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

[2]. Meunier, B.; Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104(9), 3947-3980.
https://doi.org/10.1021/cr020443g

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

[4]. Kuchynka, D. J.; Kochi, J. K. Inorg. Chem. 1988, 27, 2574-2581.
https://doi.org/10.1021/ic00288a005

[5]. 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

[6]. 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

[7]. 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

[8]. 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

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

[10]. Pierpont, C. G.; Lange, C. W. Prog. Inorg. Chem. 2007, 41(1), 331-442.
https://doi.org/10.1002/9780470166420.ch5

[11]. Pierpont, C. G.; Buchanan, R. M. Coord. Chem. Rev. 1981, 38(1), 45-87.
https://doi.org/10.1016/S0010-8545(00)80499-3

[12]. Pierpont, C. G. Coord. Chem. Rev. 2001, 219-221, 415-433.
https://doi.org/10.1016/S0010-8545(01)00342-3

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

[14]. 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

[15]. Bill, E.; Bothe, E.; Chaudhuri, P.; Chlopek, K.; Herebian, D.; Kokatam, S. Chem. Eur. J. 2005, 11(1), 204-224.
https://doi.org/10.1002/chem.200400850

[16]. Chun, H.; Verani, C. N.; Chaudhuri, P.; Bothe, E.; Bill, E.; Weyhermuller, T.; Wieghardt, K. Inorg. Chem. 2001, 40(17), 4157-4166.
https://doi.org/10.1021/ic010106a

[17]. 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

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

[19]. 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

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

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

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

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

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

[25]. 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.

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

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

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

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

[30]. 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

[31]. 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

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

[33]. 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

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

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

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

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

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

[39]. 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

[40]. 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

[41]. Krishnakumar, V.; Dheivamalar, S.; Xavier, R. J.; Balachandran, V. Spectrochim. Acta A 2006, 65(1), 147-154.
https://doi.org/10.1016/j.saa.2005.09.039

[42]. Arslan, H.; Florke, U.; Kulcu, N. Spectrochim. Acta A 2007, 67(3-4), 936-943.
https://doi.org/10.1016/j.saa.2006.09.011

[43]. Yesilkaynak, T.; Binzet, G.; Emen, F. M.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2010, 1(1), 1-5.
https://doi.org/10.5155/eurjchem.1.1.1-5.3

[44]. Arslan, B., MSc Thesis, Mersin University, Mersin, Turkey, 2017.

[45]. Aslantatar, E., MSc Thesis, Mersin University, Mersin, Turkey, 2013.

[46]. Spackman, M.; Jayatilaka, D. CrystEngComm. 2009, 11, 19-32.
https://doi.org/10.1039/B818330A

[47]. McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. 2007, 267, 3814-3816;
https://doi.org/10.1039/b704980c

[48]. McKinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Chem. A Eur. J. 1998, 4, 2136-214.
https://doi.org/10.1002/(SICI)1521-3765(19981102)4:11<2136::AID-CHEM2136>3.0.CO;2-G

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