European Journal of Chemistry 2019, 10(4), 323-335 | doi: https://doi.org/10.5155/eurjchem.10.4.323-335.1920 | Get rights and content






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


Immihan Sezen Aydogdu (1,*) orcid , Ilkay Gumus (2) orcid , Hakan Arslan (3) orcid

(1) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey
(2) Department of Basic Sciences, Faculty of Maritime, Mersin University, Mersin, 33343, Turkey
(3) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey
(*) Corresponding Author

Received: 24 Aug 2019 | Revised: 17 Oct 2019 | Accepted: 22 Oct 2019 | Published: 31 Dec 2019 | Issue Date: December 2019

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.


Keywords


Acetamide; Vibration spectrum; Ab-initio calculations; Redox active compound; Density functional theory; Hirshfeld surface analysis

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DOI: 10.5155/eurjchem.10.4.323-335.1920

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Funding information


This study was supported by Research Fund of Mersin University in Turkey with Project Number: 2018-1-TP2-2799.

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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How to cite


Aydogdu, I.; Gumus, I.; Arslan, H. Eur. J. Chem. 2019, 10(4), 323-335. doi:10.5155/eurjchem.10.4.323-335.1920
Aydogdu, I.; 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(4), 323-335. doi:10.5155/eurjchem.10.4.323-335.1920
Aydogdu, I., Gumus, I., & Arslan, H. (2019). Hirshfeld surface and theoretical studies of 2,2,2-trichloro-N,N-bis(2-(2,2,2-trichloroacetamido)phenyl)acetamide compound. European Journal of Chemistry, 10(4), 323-335. doi:10.5155/eurjchem.10.4.323-335.1920
Aydogdu, Immihan, Ilkay Gumus, & Hakan Arslan. "Hirshfeld surface and theoretical studies of 2,2,2-trichloro-N,N-bis(2-(2,2,2-trichloroacetamido)phenyl)acetamide compound." European Journal of Chemistry [Online], 10.4 (2019): 323-335. Web. 11 Aug. 2020
Aydogdu, Immihan, Gumus, Ilkay, AND Arslan, Hakan. "Hirshfeld surface and theoretical studies of 2,2,2-trichloro-N,N-bis(2-(2,2,2-trichloroacetamido)phenyl)acetamide compound" European Journal of Chemistry [Online], Volume 10 Number 4 (31 December 2019)

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