Abstract
A theoretical study on the structure and nature of the Mn-X bond in tetraphenylporphyrin and its manganoporphyrines containing halogen as an axial ligand [Mn(TPP)X] {X=F, Cl and Br} was carried through density functional B3LYP/6-311G and M06/def2TZVP methods. Comparison of length and angle of bonds in the optimized geometry of [Mn(TPP)Cl] to its X-ray single crystal structure revealed that M06/def2TZVP basis set resulted in more realistic outcomes. Furthermore, the Mn–X bond was analyzed using AIM and NBO to obtain its nature and order in the presence of different halogen axial ligands. The results showed that the Mn-X bond has a σ nature with no π-back donation from Mn to X ligand and the bond order decreased from F to Br. In addition, the effect of axial ligands on the global and local chemical reactivity descriptors of manganoporphyrins has been discussed.
Similar content being viewed by others
References
S. Tong, Y.E. von Schirnding, T. Prapamontol, Bull. World Health Organ. 78, 1068 (2000)
L. Giribabu, K. Sudhakar, J. Photochem. Photobiol. A Chem. 296, 11 (2015)
F. D’Souza, O. Ito, Chem. Soc. Rev. 41, 86 (2012)
D. Gust, T.A. Moore, A.L. Moore, Acc. Chem. Res. 42, 1890 (2009)
M. Yu, J. Li, W. Sun, M. Jiang, F. Zhang, J. Mater. Sci. 49, 5519 (2014)
M.E. El-Khouly, D.K. Ju, K.-Y. Kay, F. D’Souza, S. Fukuzumi, Chem. A Eur. J. 16, 6193 (2010)
G. Pagona, G.E. Zervaki, A.S.D. Sandanayaka, O. Ito, G. Charalambidis, T. Hasobe, A.G. Coutsolelos, N. Tagmatarchis, J. Phys. Chem. C 116, 9439 (2012)
C.M. Davis, K. Ohkubo, A.D. Lammer, D.S. Kim, Y. Kawashima, J.L. Sessler, S. Fukuzumi, Chem. Commun. 51, 9789 (2015)
T. Ripolles-Sanchis, B.-C. Guo, H.-P. Wu, T.-Y. Pan, H.-W. Lee, S.R. Raga, F. Fabregat-Santiago, J. Bisquert, C.-Y. Yeh, E.W.-G. Diau, Chem. Commun. 48, 4368 (2012)
B. Basheer, D. Mathew, B.K. George, C.P. Reghunadhan-Nair, Sol. Energy 108, 479 (2014)
J. Kandhadi, R.K. Kanaparthi, L. Giribabu, J. Porphyr, Phthalocyanines 16, 282 (2012)
L. Giribabu, P.S. Reeta, R.K. Kanaparthi, M. Srikanth, Y. Soujanya, J. Phys. Chem. A 117, 2944 (2013)
F.C. Gong, D.-X. Wu, Z. Cao, X.-C. He, Biosens. Bioelectron. 22, 423 (2006)
V.A. Montes, C. Pérez-Bolívar, N. Agarwal, J. Shinar, J.P. Anzenbacher, ACS Nano 128, 12436 (2006)
M.L. Seol, S.J. Choi, C.-H. Kim, D.-I. Moon, Y.-K. Choi, ACS Nano 6, 183 (2012)
S.V. Rao, N.K.M. Naga-Srinivas, D.N. Rao, L. Giribabu, B.G. Maiya, R. Philip, G.R. Kumar, Opt. Commun. 192, 123 (2001)
L. Giribabu, R.K. Kanaparthi, V. Velkannan, Chem. Rec. 12, 306 (2012)
R. Kanaparthi, J. Kandhadi, Tetrahedron 68, 8383 (2012)
S.K. Ghosh, M. Berkowitz, J. Chem. Phys. 83, 2976 (1985)
F. Xin-Tian, J. Yu, M. Lei, W. Fang, S. Liu, J. Phys. Chem. B 113, 13381 (2009)
S. Arun, R. Singh, R. Pathak, D. Shukla, P. Yadav, J. Mol. Struc. 1201, 127136 (2020)
E. Serpil, M. Gul, E. İnkaya, Ind. J. Chem. Tech. 26, 235 (2019)
C. VineetKumar, A. Bhatt, D. Dash, N. Sharma, J. Comp. Chem. 40, 2354 (2019)
M. Virendra, N. Sekar, J. fluorescence 27, 1101 (2017)
L.H. Mendoza-Huizar, H. Rios-Reyes, G.A. Álvarez-Romero, M.E. Palomar-Pardavé, M.T. Ramírez-Silva, J. Chilean Chem. Soc. 62, 3411 (2017)
G. Tim, J. Chem. Theo. Comp. 13, 2373 (2017)
G. Paul, E. Chamorro, P. Chattaraj, F. Proft, J.L. Gázquez, S. Liu, C. Morell, A. Toro-Labbé, A. Vela, P. Ayers, Theor. Chem. Acc. 139, 36 (2020)
S. Tsutomu, K. Nabeshima, M. Yasuda, H. Inoue, Chem. Lett. 32, 148 (2003)
I.A. Oskina, V.M. Vlasov, Russ. J. Org. Chem. 37, 260 (2001)
M. J. Frisch, G. W. Trucks, H. B. Schlegal, G. E. Scuseria, M. A. Robb, Gaussian09, Revision A.02, Gaussian Inc., Wallingford, CT (2009)
GaussView, Version 6.1, R. Dennington, T. A. Keith, J. M. Millam, Semichem Inc., Shawnee Mission, KS (2016)
C. Lee, W. Yang, R.G. Parr, Phys. Rev. B. 37, 785 (1988)
R. Krishnan, J. Binkley, R. Seeger, J. Pople, J. Chem. Phys. 72, 650 (1950)
C. Catherine, T.O. Faust, J.M. Bailey, B.J. Wright, T.M. Gilbert, L.S. Sunderlin, J. Phys. Chem. A 105, 8111 (2001)
Z. Yan, D.G. Truhlar, Theor. Chem. Acc. 120, 215 (2008)
Z. Jingjing, X. Xu, D.G. Truhlar, Theor. Chem. Acc. 128, 295 (2011)
L. Pauling, The Nature of the Chemical Bond and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry (Cornell University Press, New York, 1960)
R.F.W. Bader, T.T. Nguyen-Dang, Adv. Quant. Chem. 14, 63 (1981)
AIMAll (Version 19.10.12), Todd A. Keith, TK Gristmill Software, Overland Park KS, USA (2019)
M.S. Masoud, A.E. Ali, M.A. Shaker, G.S. Elasala, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 90, 93 (2012)
R.G. Pearson, J. Org. Chem. 54, 1423 (1989)
J. Padmanabhan, R. Parthasarathi, V. Subramanian, P.K. Chattaraj, J. Mol. Struc. 774, 49 (2006)
A.A. Recio-Despaigne, J.G. Da Silva, A.C.M. Do-Carmo, O.E. Piro, E.E. Castellano, H. Beraldo, J. Mol. Struct. 920, 97 (2009)
P. Florian, V.K.K. Praneeth, C. Näther, N. Lehnert, Inorg. Chem. 45, 2835 (2006)
D. Bene, E. Janet, H. Donald, I. Shavitt, J. Am. Chem. Soc. 114, 1631 (1992)
T.A. Yousef, G.M. Abu El-Reash, R.M. El-Morshedy, Polyhedron 45, 71 (2012)
L. Liu, M.S. Alam, D.-U. Lee, Bull. Korean Chem. Soc. 33, 3361 (2012)
D. Chen, A.E. Martell, Inorg. Chem. 26, 1026 (1987)
M. Govindarajan, S. Periandy, K. Carthigayen, Spectrochim Acta Part A Mol. Biomol. Spectrosc. 97, 411 (2012)
P. Thanikaivelan, J. Padmanabhan, V. Subramanian, T. Ramasami, Theor. Chem. Acc. 107, 326 (2002)
A.T. Maynard, M. Huang, W.G. Rice, D.G. Covell, Proc. Natl. Acad. Sci. U. S. A. 95, 11578 (1998)
R.G. Parr, P.K. Chattaraj, J. Am. Chem. Soc. 113, 1854 (1991)
R.G. Parr, L.V. Szentpaly, S. Liu, J. Am. Chem. Soc. 121, 1922 (1999)
P. Politzer, J.S. Murray, J. Mol. Model. 24, 214 (2018)
B. Jannik, Chem. Rev. 46, 381 (1950)
R. Parthasarathi, Internet Electron. J. Mol. Des. 2, 798 (2003)
R.G. Parr, W. Yang, J. Am. Chem. Soc. 106, 4049 (1984)
R.G. Parr, in Horizons Quantum Chem (Springer, Netherlands, Dordrecht, 1980), pp. 5–15
O.A. El-Gammal, Spectrochim Acta Part A Mol. Biomol. Spectrosc. 75, 533 (2010)
D. X. West, J. K. Swearingen, J. Valdés-Martı́nez, S. Hernández-Ortega, A. K. El-Sawaf, F. van Meurs, A. Castiñeiras, I. Garcia, E. Bermejo, Polyhedron 18, 2919 (1999)
A. A. R. Despaigne, J. G. da Silva, A. C. M. do Carmo, F. Sives, O. E. Piro, E. E. Castellano, H. Beraldo, Polyhedron 28, 3797 (2009)
W. Yang, W.J. Mortier, J. Am. Chem. Soc. 108, 5708 (1986)
F. Hartl, P. Rosa, L. Ricard, P.L. Floch, S. Záliš, Coord. Chem. Rev. 251, 557 (2007)
L. Leherte, D.P. Vercauteren, Mol. Model. Ann. 3, 156 (1997)
S.J. Grabowski, W.A. Sokalski, E. Dyguda, J. Leszczyński, J. Phys. Chem. B 110, 6444 (2006)
Acknowledgements
The authors are grateful to the Research Council of Persian Gulf University for the support of this study.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Babaei, S., Niad, M. & Solati, Z. DFT investigation onto axial ligand effects on the TPP ligand and its manganese complexes [Mn(TPP)(O)(X)] (X=F-, Cl-, Br-). J IRAN CHEM SOC 17, 2901–2908 (2020). https://doi.org/10.1007/s13738-020-01966-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-020-01966-3