Abstract
Tetrazole- and nitrile-containing bimesitylene derivatives with potential use in coordination chemistry were synthesized and characterized, and their structural particularities are discussed. For the bimesitylene bistetrazole derivative, geometry optimization was carried out by quantum-chemical calculations using density functional theory together with vibrational frequencies, natural bond orbitals, and highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) calculations. The newly synthesized bimesitylene derivatives were also evaluated for their antimicrobial activity against three different reference strains, namely Escherichia coli, Staphylococcus aureus, and Candida albicans.
Similar content being viewed by others
Notes
http://www.yasara.org—YASARA official site (Yet Another Scientific Artificial Reality Application).
References
J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 102, 1359 (2002)
C. Janiak, J.K. Vieth, New J. Chem. 34, 2366 (2010)
J.N. Moorthy, R. Natarajan, P. Venugopalan, J. Org. Chem. 70, 8568 (2005)
W. Lu, Z. Wei, D. Yuan, J. Tian, S. Fordham, H.C. Zhou, Chem. Mater. 26, 4589 (2014)
J.N. Moorthy, R. Natarajan, G. Savitha, P. Venugopalan, Cryst. Growth Des. 6(4), 919 (2006)
C.X. Wei, M. Bian, G.H. Gong, Molecules 20, 5528 (2015)
K. Adil, Y. Belmabkhout, R.S. Pillai, A. Cadiau, P.M. Bhatt, A.H. Assen, G. Maurin, M. Eddaoudi, Chem. Soc. Rev. 46, 3402 (2017)
L.J. Chen, H.B. Yang, M. Shionoya, Chem. Soc. Rev. 46, 2555 (2017)
L.R. Mingabudinova, V.V. Vinogradov, V.A. Milichko, E. Hey-Hawkins, A.V. Vinogradov, Chem. Soc. Rev. 45, 5408 (2016)
M. Eddaoudi, D.F. Sava, J.F. Eubank, K. Adila, V. Guillerm, Chem. Soc. Rev. 44, 228 (2015)
Y.X. Tan, F. Wang, J. Zhang, Chem. Soc. Rev. 47, 2130 (2018)
V. Karunakaran, V. Balachandran, Spectrochim. Acta A 98, 229 (2012)
A. Suvitha, S. Periandy, S. Boomadevi, M. Govindarajan, Spectrochim. Acta A 117, 216 (2014)
M. Karabacak, E. Sahin, M. Cinar, I. Erol, M. Kurt, J. Mol. Struct. 886, 148 (2008)
I. Sidir, Y.G. Sidir, M. Kumalar, E. Tasal, J. Mol. Struct. 964, 134 (2010)
G. Cahiez, C. Chaboche, F. Mahuteau-Betzer, M. Ahr, Org. Lett. 7(10), 1943 (2005)
M.F. Zaltariov, C. Cojocaru, S. Shova, I. Sacarescu, M. Cazacu, J. Mol. Struct. 1120, 302 (2016)
O.M. Becker, A.D. MacKerell, B. Roux, M. Watanabe, Conformational Analysis, in Computational Biochemistry and Biophysics (Marcel Dekker, New York, 2001), pp. 69–90
J. Frau, D. Glossman-Mitnik, Molecules 23(3), 559 (2018)
R. Vijayaraj, V. Subramanian, P.K. Chattaraj, J. Chem. Theory Comput. 5(10), 2744 (2009)
C.M. Chang, Y.H. Ou, T.C. Liu, S.Y. Lu, M.K. Wang, SAR QSAR Environ. Res. 27(6), 441 (2016)
L.L. Dai, S.F. Cui, G.L.V. Damu, C.H. Zhou, Chin. J. Org. Chem. 33, 224 (2013)
J. Roh, K. Vavrova, A. Hrabalek, Eur. J. Org. Chem. 31, 6101 (2012)
C.G. Pierce, J.L. Lopez-Ribot, Expert Opin. Drug Discov. 8(9), 1177 (2013)
B. Minea, N. Marangoci, D. Peptanariu, I. Rosca, V. Năstasă, A. Corciova, C.D. Varganici, A. Nicolescu, A. Fifere, A. Neamțu, M. Mareș, M. Bărboiu, M. Pinteală, New J. Chem. 40, 1765 (2016)
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.36.32, 2003
O.V. Dolomanov, L.J. Bourhis, R.J.J. Gildea, A.K. Howard, H. Puschmann, J. Appl. Cryst. 42, 339 (2009)
G.M. Sheldrick, Acta Crystallogr. A A64, 112 (2008)
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09 (Gaussian Inc., Wallingford, CT, 2009)
R. Dennington, T. Keith, J. Millam, GaussView, Version 5 (Semichem Inc., Shawnee Mission, KS, 2009)
E. Krieger, G. Vriend, Bioinformatics 30, 2981 (2014)
J.J.P. Stewart, J. Mol. Model. 19, 1 (2013)
D.F. Brown, D. Kothari, J. Clin. Pathol. 28, 779 (1975)
Acknowledgements
Financial support from the European Social Fund for Regional Development, Competitiveness Operational Programme Axis 1—Project “Novel Porous Coordination Polymers with Organic Ligands of Variable Length for Gas Storage,” POCPOLIG (ID P_37_707, Contract 67/08.09.2016, cod MySMIS: 104810) is gratefully acknowledged. The research related to computational chemistry is part of a project that has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement no. 667387 WIDESPREAD 2-2014 SupraChem Lab.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Bahrin, L.G., Clima, L., Shova, S. et al. Synthesis, structure, computational modeling, and biological activity of two novel bimesitylene derivatives. Res Chem Intermed 45, 453–469 (2019). https://doi.org/10.1007/s11164-018-3611-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-018-3611-x