Chemical Papers

, Volume 73, Issue 3, pp 737–746 | Cite as

Theoretical study of crystalline network and optoelectronic properties of erlotinib hydrochloride molecule: non-covalent interactions consideration

  • H. A. Rahnamaye AliabadEmail author
  • M. ChahkandiEmail author
Original Paper


In this work, for the first time, we have investigated the structural and optoelectronic properties of Erlotinib hydrochloride (C22H24N3O4+·Cl) (1) anticancer drug using DFT calculations by the full-potential (linearized) augmented plane wave (FP(L)APW) calculations and hybrid density functional B3LYP. The monomeric ion of 1 participates in some 2-D fragments through different non-covalent interactions, including H-bonds (HBs) and π-stacking. Dispersion-corrected density functional theory calculations (DFT-D) have been used for obtaining the corrected values of the calculated binding energy of non-covalent interactions of the respective network of 1. Delocalization indices are the criterions for bond polarity by measuring the share of electron pair between two atoms. The results show that involved HBs can be classified from moderate to strong. The results show that HBs, especially non-covalent C–H···O interactions, govern the network formation along the a and c axes. Density of state results by the FP(L)APW show that this complex has a wide band gap (2.28 eV). The top of the valence band is originating mainly from Cl-, N- and O-p states and the bottom of the conduction band is composed of C- and N-p states. These states play a key role in optical transitions of C22H24N3O4+·Cl anticancer drug. Optical results show that this molecule is birefringent.


DFT Structural and optoelectronic properties Erlotinib hydrochloride Birefringent 



HARA and MCH gratefully acknowledge the financial support by the Hakim Sabzevari University, Sabzevar, Iran. Prof. P. Blaha, Vienna University of Technology, Austria, is appreciated for his technical help in the use of Wien2 k package.


  1. Aznar E, Marcos MD, Martinez-Manez R, Sancenon F, Soto J, Amoros P, Guillem C (2009) pH- and photo-switched release of guest molecules from mesoporous silica supports. J Am Chem Soc 131:6833–6843. CrossRefGoogle Scholar
  2. Bader RWF (1990) Atoms in molecules: a quantum theory. Oxford University Press, OxfordGoogle Scholar
  3. Barghi L, Aghanejad A, Valizadeh H, Barar J, Asgari D (2012) Modified Synthesis of Erlotinib Hydrochloride. Adv Pharm Bull 2:119–122. Google Scholar
  4. Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38(6):3098–3100. CrossRefGoogle Scholar
  5. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98(7):5648–5652. CrossRefGoogle Scholar
  6. Boys SF, Bernardi F (1970) The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol Phys 19(4):553–566. CrossRefGoogle Scholar
  7. Chahkandi M (2016) Theoretical investigation of non-covalent interactions and spectroscopic properties of a new mixed-ligand Co(II) complex. J Mol Struct 1111:193–200. CrossRefGoogle Scholar
  8. Chahkandi M, Rahnamaye Aliabad HA (2018) Role of hydrogen bonding in establishment of a crystalline network of Cu (II) complex with hydrazone-derived ligand: optoelectronic studies. Chem Pap 72:1287–1297. CrossRefGoogle Scholar
  9. Chahkandi M, Bhatti MH, Yunus U, Shaheen S, Nadeem M, Nawaz Tahir M (2017) Synthesis and comprehensive structural studies of a novel amide based carboxylic acid derivative: non-covalent interactions. J Mol Struct 1133:499–509. CrossRefGoogle Scholar
  10. Chahkandi M, Bhatti MH, Yunus U, Nadeem M, Zakaria M, Nawaz Tahir M (2018) Novel cocrystal of N-phthaloyl-b-alanine with 2,2ebipyridyl: synthesis, computational and free radical scavenging activity studies. J Mol Struct 1152:1–10. CrossRefGoogle Scholar
  11. Chattopadhyay B, Mukherjee AK, Narendra N, Hemantha HP, Sureshbabu VV, Helliwell M, Mukherjee M (2010) Supramolecular architectures in 5, 50-substituted hydantoins: crystal structures and Hirshfeld surface analyses. Crys Growth Des 10:4476. CrossRefGoogle Scholar
  12. Desiraju GR (1995) Supramolecular synthons in crystal engineering—a new organic synthesis. Angew Chem Int Ed Engl 34:2311. CrossRefGoogle Scholar
  13. Dickerson EB, Dreaden EC, Huang XH, El-Sayed IH, Chu HH, Pushpanketh S, McDonald JF, El-Sayed MA (2008) Gold nanorod assisted near-infrared plasmonic photothermal therapy (PPTT) of squamous cell carcinoma in mice. Cancer Lett. 269:57–66. CrossRefGoogle Scholar
  14. Eshtiagh-Hosseini H, Chahkandi M, Housaindokht MR, Mirzaei M (2013) Bromide oxidation mechanism by vanadium bromoperoxidase functional models with new tripodal amine ligands: a comprehensive theoretical calculations study. Polyhedron 60:93–101. CrossRefGoogle Scholar
  15. Fang W, Yang J, Gong J, Zheng N (2012) Photo- and pH-triggered release of anticancer drugs from mesoporous silica-coated Pd@Ag nanoparticles. Adv Funct Mater 22:842–848. CrossRefGoogle Scholar
  16. Fradera X, Austen MA, Bader RFW (1999) The lewis model and beyond. J Phys Chem A 103(2):304–314. CrossRefGoogle Scholar
  17. Frisch MJ, et al. (2009). G09| Retrieved September 30, 2017, from
  18. Hawrysz DJ, Sevick-Muraca EM (2000) Developments toward diagnostic breast cancer imaging using near-infrared optical measurements and fluorescent contrast agents. Neoplasia 2:388–417. CrossRefGoogle Scholar
  19. Hosseini SM, Rahnamaye Aliabad HA, Kompany A (2005) First principle study of optical properties of pure α-Al2O3 and La aluminates. Eur phys J B. 43:439–444. CrossRefGoogle Scholar
  20. Jurecka P, Cerny J, Hobza P, Salahub DR (2007) Density functional theory augmented with an empirical dispersion term. Interaction energies and geometries of 80 noncovalent complexes compared with ab initio quantum mechanics calculations. J Comput Chem 28:555. CrossRefGoogle Scholar
  21. Lee C, Yang W, Parr RG (1988) Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37(2):785–789. CrossRefGoogle Scholar
  22. Lin QN, Huang Q, Li CY, Liu ZZ, Li FY, Zhu LY (2010) Anticancer drug release from a mesoporous silica based nanophotocage regulated by either a one- or two-photon process. J Am Chem Soc. 132:10645–10647. CrossRefGoogle Scholar
  23. Mirzaei M, Eshtiagh-Hosseini H, Chahkandi M, Alfi N, Shokrollahi A, Shokrollahi N, Janiak A (2012) Comprehensive studies of non-covalent interactions within four new Cu(ii) supramolecules. Cryst Eng Comm 14(24):8468. CrossRefGoogle Scholar
  24. Moyer JD, Barbacci EG, Iwata KK, Arnold L, Boman B, Cunningham A, Diorio C, Doty J, Morin MJ, Moyer MP, Neveu M, Pollack VA, Pustilnik LR, Reynolds MM, Sloan D, Theleman A, Miller P (1997) Induction of apotosis and cell cycle arrest by CP-358,774, an inhibitor of epidermal growth factor receptor tyrosine kinase. Cancer Res. 57:4838–4848Google Scholar
  25. Perdew JP, Burke K, Ernzerhof M (1996) Generalized gradient approximation made simple. Phys Rev Lett 77:3865–3868. CrossRefGoogle Scholar
  26. Petersen M, Wagner F, Hufnagel L, Scheffler M, Blaha P, Schwarz K (2000) Improving the efficiency of FP-LAPW calculations. Comput Phys Commun 126(3):294–309. CrossRefGoogle Scholar
  27. Rahnamaye Aliabad HA (2015) Investigation of optoelectronic properties of pure and Co substituted a-Al2O3 by Hubbard and modified Becke-Johnson exchange potentials. Chin Phys B 24:097102. CrossRefGoogle Scholar
  28. Rahnamaye Aliabad HA, Ahmed I (2012) Optoelectronic properties of LixAxNbO3 (A = Na, K, Rb, Cs, Fr) crystals. Physica B: Condensed Matter 407:368–377. CrossRefGoogle Scholar
  29. Rahnamaye Aliabad HA, Chahkandi M (2017a) Optoelectronic and structural studies of a Ni(II) complex including bicyclic guanidine ligands: FPLAPW and B3LYP–DFT approaches. Computational and Theoretical Chemistry 1122:53–61. CrossRefGoogle Scholar
  30. Rahnamaye Aliabad HA, Chahkandi M (2017b) Comprehensive SPHYB and B3LYP–DFT studies of two types of Ferrocene. Zeitschrift für anorganische und allgemeine Chemie. 643:420–431. CrossRefGoogle Scholar
  31. Rahnamaye Aliabad HA, Yalcin BG (2015) Effects of IIIB transition metals on optoelectronic and magnetic properties of HoMnO3: A first principles study. Chin. Phys. B 24:117102. CrossRefGoogle Scholar
  32. Rahnamaye Aliabad HA, Yalcin BG (2017) Optoelectronic and thermoelectric response of Ca5Al2Sb6 to shift of band gap from direct to indirect. J Mater Sci: Mater Electron 28:14954–14964. Google Scholar
  33. Rahnamaye Aliabad HA, Hosseini SM, Kompany A, Youssefi A, Attaran E (2009) Optical properties of pure and transition metal-doped indium oxide. Phys. stat. sol. (b) 246:1072–1081. CrossRefGoogle Scholar
  34. Rahnamaye Aliabad HA, Asadi Y, Ahmed I (2012a) Quasiparticle optoelectronic properties of pure and doped Indium Oxide. Opt Mater 34:1406–1414. CrossRefGoogle Scholar
  35. Rahnamaye Aliabad HA, Ghazanfari M, Ahmad I, Saeed MA (2012b) Ab initio calculations of structural, optical and thermoelectric properties for CoSb3 and ACo4Sb12 (A = La, Tl and Y) compounds. Comput Mater Sci 65:509–519. CrossRefGoogle Scholar
  36. Rahnamaye Aliabad HA, Fathabadi M, Ahmad I (2013) Optoelectronic properties of KDP by first principle calculations. Int J Quantum Chem 113:865–872. CrossRefGoogle Scholar
  37. Rahnamaye Aliabad HA, Tayebee R, Boroumand Khalili M (2015) Ab initio studies of optoelectronic properties of fluorine-substituted ferrocene. Research on Chemical Intermediates 42:3743–3761. CrossRefGoogle Scholar
  38. Rahnamaye Aliabad HA, Mojarradi Z, Yalcin BG (2016) DFT studies for optoelectronic properties of pure l-alanine and doped with Li. Journal of Materials Science: Materials in Electronics 27:4887–4897. Google Scholar
  39. Rahnamaye Aliabad HA, Vaezi H, Basirat S, Ahmad I (2017) Role of the Crystal Lattice Constants and Band Structures in the Optoelectronic Spectra of CdGa2S4 by DFT Approaches. Z Anorg Allg Chem 643:839–849. CrossRefGoogle Scholar
  40. Riley KE, Pitoňák M, Jurečka P, Hobza P (2010) Stabilization and structure calculations for noncovalent interactions in extended molecular systems based on wave function and density functional theories. Chem Rev 110(9):5023–5063. CrossRefGoogle Scholar
  41. Selvanayagam S, Sridharb B, Ravikumarb K (2008) Erlotinib hydrochloride: an anticancer, Agent. Acta Cryst. E 64:o931. CrossRefGoogle Scholar
  42. Seth SK, Saha I, Estarellas C, Frontera A, Kar T, Mukhopadhyay S (2011) Supramolecular self-assembly of M-IDA complexes involving lone-pair···π interactions: crystal structures, hirshfeld surface analysis, and DFT calculations [H 2 IDA = iminodiacetic acid, M = Cu(II), Ni(II)]. Cryst Growth Des 11(7):3250–3265. CrossRefGoogle Scholar
  43. Wang S, Chen KJ, Wu TH, Wang H, Lin WY, Ohashi M, Chiou PY, Tseng HR (2010) Photothermal Effects of Supramolecularly Assembled Gold Nanoparticles for the Targeted Treatment of Cancer Cells. Angew. Chem. Int. Edit. 49:3777–3781. CrossRefGoogle Scholar
  44. Weissleder R (2001) A clearer vision for in vivo imaging. Nat. Biotechnol. 19:316–317. CrossRefGoogle Scholar
  45. Yang Y, Song WX, Wang AH, Zhu PL, Fei JB, Li JB (2010) Lipid coated mesoporous silica nanoparticles as photosensitive drug carriers. Phys. Chem. Chem. Phys. 12:4418–4422. CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of PhysicsHakim Sabzevari UniversitySabzevarIran
  2. 2.Department of ChemistryHakim Sabzevari UniversitySabzevarIran

Personalised recommendations