Vibrational Spectroscopic Characterization and DFT Study of Palladium(ii) Complexes with N-Benzyliminodiacetic Acid Derivatives
Neven Smrečki A B , Igor Rončević A and Zora Popović A
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia.
B Corresponding author: Email: nsmrecki@chem.pmf.hr
Australian Journal of Chemistry 69(11) 1285-1291 https://doi.org/10.1071/CH16150
Submitted: 11 March 2016 Accepted: 5 May 2016 Published: 10 June 2016
Abstract
The reactions of N-benzyliminodiacetic acid (BnidaH2) and its para-substituted derivatives, namely N-(p-chlorobenzyl)iminodiacetic acid (p-ClBnidaH2), N-(p-nitrobenzyl)iminodiacetic acid (p-NO2BnidaH2), and N-(p-methoxybenzyl)iminodiacetic acid (p-MeOBnidaH2) with sodium tetrachloropalladate(II) were performed in aqueous solutions. Three new complexes [Pd(p-ClBnidaH)2]·2H2O (2), [Pd(p-NO2BnidaH)2]·2H2O (3), and [Pd(p-MeOBnidaH)2] (4) were prepared and characterized by infrared spectroscopy and thermogravimetric and differential thermal analyses. The molecular geometry and infrared spectra of these three complexes, together with the previously synthesized [Pd(BnidaH)2]·2H2O (1a) and [Pd(BnidaH)2] (1b) were also modelled using density functional theory calculations at the BP86/6–311+G(d,p) level of theory with SDD pseudopotentials.
References
[1] F. P. Dwyer, D. P. Mellor, Chelating Agents and Metal Chelates 1964 (Academic Press: New York, NY).[2] E. Müller, O. Bayer, H. Meerwein, K. Ziegler, Methoden der Organischen Chemie (Houben-Weyl), Band XI/2 – Stickstoffverbindungen II und III 1958 (Georg Thieme Verlag: Stuttgart).
[3] C. F. Bell, Principles and Applications of Metal Chelation 1977 (Oxford University Press: Oxford).
[4] I. N. Polyakova, A. L. Poznyak, V. S. Sergienko, Crystallogr. Rep. 2000, 45, 762.
| Crossref | GoogleScholarGoogle Scholar |
[5] D. K. Patel, D. Choquesillo-Lazarte, J. M. González-Perez, A. Domínguez-Martín, A. Matilla-Hernandez, A. Castiñeiras, J. Niclós-Gutiérrez, Polyhedron 2010, 29, 683.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmvVentQ%3D%3D&md5=d9ee8cf672cc13524fd36af0a67abb92CAS |
[6] E. Bugella-Altamirano, D. Choquesillo-Lazarte, J. M. González-Perez, M. J. Sánchez-Moreno, R. Marín-Sánchez, J. D. Martín-Ramos, B. Covelo, R. Carballo, A. Castiñeiras, J. Niclós-Gutiérrez, Inorg. Chim. Acta 2002, 339, 160.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XosFOltbg%3D&md5=34e0b9f9757a910e8c0caf2fffdd4e48CAS |
[7] M. J. Sánchez-Moreno, D. Choquesillo-Lazarte, J. M. González-Perez, R. Carballo, A. Castiñeiras, J. Niclós-Gutiérrez, Inorg. Chem. Commun. 2002, 5, 800.
| Crossref | GoogleScholarGoogle Scholar |
[8] D. Choquesillo-Lazarte, A. Domínguez-Martín, A. Matilla-Hernandez, C. S. de Medina-Revilla, J. M. González-Perez, A. Castiñeiras, J. Niclós-Gutiérrez, Polyhedron 2010, 29, 170.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhs1Smt7jM&md5=b021a7dba1177819d634810e20349392CAS |
[9] A. Domínguez-Martín, D. Choquesillo-Lazarte, J. M. González-Perez, A. Castiñeiras, J. Niclós-Gutiérrez, J. Inorg. Biochem. 2011, 105, 1073.
| Crossref | GoogleScholarGoogle Scholar | 21726770PubMed |
[10] M. J. Sánchez-Moreno, D. Choquesillo-Lazarte, J. M. González-Perez, R. Carballo, J. D. Martín-Ramos, A. Castiñeiras, J. Niclós-Gutiérrez, Polyhedron 2003, 22, 1039.
| Crossref | GoogleScholarGoogle Scholar |
[11] D. K. Patel, D. Choquesillo-Lazarte, A. Domínguez-Martín, M. P. Brandi-Blanco, J. M. González-Perez, A. Castiñeiras, J. Niclós-Gutiérrez, Inorg. Chem. 2011, 50, 10549.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlSltbbJ&md5=f11e7afc9c92ab9b96fe2bf3921af941CAS | 21995280PubMed |
[12] A. Domínguez-Martín, D. Choquesillo-Lazarte, J. A. Dobado, I. Vidal, L. Lezama, J. M. González-Pérez, A. Castiñeiras, J. Niclós-Gutiérrez, Dalton Trans. 2013, 42, 6119.
| Crossref | GoogleScholarGoogle Scholar | 23324859PubMed |
[13] A. Domínguez-Martín, D. Choquesillo-Lazarte, J. A. Dobado, H. Martínez-García, L. Lezama, J. M. González-Pérez, A. Castiñeiras, J. Niclós-Gutiérrez, Inorg. Chem. 2013, 52, 1916.
| Crossref | GoogleScholarGoogle Scholar | 23356582PubMed |
[14] N. Smrečki, B.-M. Kukovec, M. Đaković, Z. Popović, Inorg. Chim. Acta 2013, 400, 122.
| Crossref | GoogleScholarGoogle Scholar |
[15] J. Chakraborty, M. K. Saha, P. Banerjee, Inorg. Chem. Commun. 2007, 10, 671.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXlt1Shs7Y%3D&md5=56f9e7072601292b914cc52f60b3d708CAS |
[16] J. Chakraborty, H. Mayer-Figge, W. S. Sheldrick, P. Banerjee, Polyhedron 2005, 24, 771.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjs1GitLk%3D&md5=b6230fa8c65365b3099e2f6a9deecebdCAS |
[17] I. N. Polyakova, T. N. Polynova, M. A. Porai-Koshits, A. M. Grevtsev, J. Struct. Chem. 1979, 20, 574.
| Crossref | GoogleScholarGoogle Scholar |
[18] A. L. Poznyak, A. B. Ilyukhin, V. S. Sergienko, Russ. J. Inorg. Chem. 1997, 42, 1660.
| 1:CAS:528:DyaK2sXotVartrk%3D&md5=6e120eaf9c6825175a0e91e6ad886511CAS |
[19] R.-F. Song, C.-Z. Zhang, F. Li, S.-C. Jin, Z.-S. Jin, Chem. Res. Chin. Univ. 1992, 8, 399.
| 1:CAS:528:DyaK3sXmsVShtbk%3D&md5=2a56fc4a6798e733875e5d0d280286f8CAS |
[20] I. N. Polyakova, A. L. Poznyak, V. S. Sergienko, Crystallogr. Rep. 2003, 48, 278.
[21] J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry 2001 (Oxford University Press: Oxford).
[22] J. Tsuji, Palladium Reagents and Catalysts 2004 (Wiley: Chichester).
[23] N. Smrečki, B.-M. Kukovec, J. Jazwinski, Y. Liu, J. Zhang, A.-M. Mikecin, Z. Popović, J. Organomet. Chem. 2014, 760, 224.
| Crossref | GoogleScholarGoogle Scholar |
[24] M. T. Bilkan, Ş. Yurdakul, Z. Demircioğlu, O. Büyükgüngör, J. Organomet. Chem. 2016, 805, 108.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28Xhtl2mtL0%3D&md5=067e66e6ecccfa80f6015685229213adCAS |
[25] N. Mhadhbi, S. Saïd, S. Elleuch, T. Lis, H. Naïli, J. Mol. Struct. 2016, 1105, 16.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhslCmsbjE&md5=440a55b63da298ec4299b83e46550d1bCAS |
[26] H. L. Singh, J. B. Singh, S. Bhanuka, J. Coord. Chem. 2016, 69, 343.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhvFOls7nN&md5=d2d9b4ef3241e7671388d59d69289757CAS |
[27] R. M. Clarke, K. Hazin, J. R. Thompson, D. Savard, K. E. Prosser, T. Storr, Inorg. Chem. 2016, 55, 762.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XlsVOkuw%3D%3D&md5=a2e3ba2998fddf6de94a54df5dbd5dfcCAS | 26719989PubMed |
[28] M. Mirzaei, H. Eshtiagh-Hosseini, M. Bazargan, F. Mehrzad, M. Shahbazi, J. T. Mague, A. Bauzá, A. Frontera, Inorg. Chim. Acta 2015, 438, 135.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhsFGhsbnP&md5=c1808642681ed2967f00eb37af95608cCAS |
[29] B. Trzaskowski, S. G. Stepanian, A. Leś, P. A. Deymier, R. Guzman, L. Adamowicz, J. Comput. Theor. Nanosci. 2006, 3, 775.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFygsLvJ&md5=47a501d93e1a9cb90380c1aab91bca5dCAS |
[30] S. Khatua, D. R. Roy, M. Bhattacharjee, P. K. Chattaraj, J. Comput. Methods Sci. Eng. 2007, 7, 395.
| 1:CAS:528:DC%2BD1cXpt1yjtr4%3D&md5=b719baa3144154d37088251015099c0bCAS |
[31] B. Trzaskowski, R. Guzman, L. Adamowicz, Polyhedron 2007, 26, 2477.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXnsValt78%3D&md5=70f36f5f19c8f4447c8ab21034e9cae3CAS |
[32] A. Bhaskarapillai, S. Chandra, N. V. Sevilimedu, B. Sellergren, Biosens. Bioelectron. 2009, 25, 558.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlWgu7vJ&md5=81c08e665180dd30fd8704d40710451fCAS | 19414245PubMed |
[33] A. R. McDonald, Y. Guo, V. V. Vu, E. L. Bominaar, E. Münck, L. Que, Chem. Sci.) 2012, 3, 1680.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XkvVKrtLw%3D&md5=5c1e1bc35c8618769d8f1c63ee4fe05cCAS | 23267430PubMed |
[34] M. S. Bukharov, V. G. Shtyrlin, G. V. Mamin, S. Stapf, C. Mattea, A. S. Mukhtarov, N. Y. Serov, E. M. Gilyazetdinov, Inorg. Chem. 2015, 54, 9777.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhs1eqsLfO&md5=9275736880be46f3971f946711ac11b8CAS | 26440723PubMed |
[35] E. Müller, O. Bayer, H. Meerwein, K. Ziegler, Methoden der Organischen Chemie (Houben-Weyl), Band XI/1 – Stickstoffverbindungen II 1957 (Georg Thieme Verlag).
[36] W. A. Jacobs, M. Heidelberger, J. Biol. Chem. 1915, 20, 659.
| 1:CAS:528:DyaC2MXhtVertQ%3D%3D&md5=9dcc68d59f01128aeb35077c7758a25eCAS |
[37] R. M. Silverstein, F. X. Webster, D. Kiemle, Spectrometric Identification of Organic Compounds, seventh ed. 2005 (Wiley: New York, NY).
[38] K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, sixth ed. 2009 (Wiley: Hoboken).
[39] G. B. Deacon, R. J. Phillips, Coord. Chem. Rev. 1980, 33, 227.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXjvVOqsw%3D%3D&md5=1a4f21ada28a455fb3bca4256ac50184CAS |
[40] G. Pirc, J. Stare, J. Mavri, J. Chem. Phys. 2010, 132, 224506.
| Crossref | GoogleScholarGoogle Scholar | 20550407PubMed |
[41] J. Stare, J. Mavri, J. Grdadolnik, J. Zidar, Z. B. Maksić, R. Vianello, J. Phys. Chem. B 2011, 115, 5999.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXltFGlsbk%3D&md5=283cbef96a74ed69adf1e6a6fd1090a0CAS | 21517054PubMed |
[42] M. Brela, J. Stare, G. Pirc, M. Sollner-Dolenc, M. J. Wójcik, J. Mavri, J. Phys. Chem. B 2012, 116, 4510.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XktVyntL4%3D&md5=a86e136bddda9d743dbbaeb378a2ec65CAS | 22429110PubMed |
[43] M. Z. Brela, M. J. Wójcik, M. Boczar, R. Hashim, Chem. Phys. Lett. 2013, 558, 88.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtF2qsLY%3D&md5=fe87ba657ab2b5b3e602feb31d6b8c6bCAS |
[44] G. Rowley, A. L. Greenleaf, G. I. Kenyon, J. Am. Chem. Soc. 1971, 93, 5542.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38XhtF2k&md5=ffb11db1302cd949bf6566118a03ef4bCAS | 5165680PubMed |
[45] S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104.
| Crossref | GoogleScholarGoogle Scholar | 20423165PubMed |
[46] C. J. Cramer, D. G. Truhlar, Phys. Chem. Chem. Phys. 2009, 11, 10757.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVentrfK&md5=d056e67661aa80c2dc7f189d7550778dCAS | 19924312PubMed |
[47] L. Goerigk, S. Grimme, Phys. Chem. Chem. Phys. 2011, 13, 6670.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjsFKkurg%3D&md5=e14b3264277795b501b27acdcbf9b41aCAS | 21384027PubMed |
[48] A. V. Soldatova, M. Ibrahim, T. G. Spiro, Inorg. Chem. 2013, 52, 7478.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXptlCntb8%3D&md5=ccb3d6e7f3b9f41fbb3cb58d4d9a2872CAS | 23763617PubMed |
[49] T. T. Tavares, D. Paschoal, E. V. S. Motta, A. G. Carpanez, M. T. P. Lopes, E. S. Fontes, H. F. Dos Santos, H. Silva, R. M. Grazul, A. P. S. Fontes, J. Coord. Chem. 2014, 67, 956.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXls1elsL4%3D&md5=10ab929473207c69672713c9db5a13a2CAS |
[50] T. Weymuth, E. P. A. Couzijn, P. Chen, M. Reiher, J. Chem. Theory Comput. 2014, 10, 3092.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVaht7rP&md5=915d68aa063267fbcb91f8a776d7eefcCAS | 26588280PubMed |
[51] 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 Jr, 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, Revision D.01 2009 (Gaussian, Inc.: Wallingford, CT).
