A DFT Study on Estrone - TNT Interaction

TÜRKER B. L., Bayar C. C.

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, vol.639, no.10, pp.1871-1875, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 639 Issue: 10
  • Publication Date: 2013
  • Doi Number: 10.1002/zaac.201300239
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1871-1875
  • Keywords: DFT, Estrogens, Estrone, pi Complex, Trinitrotoluene (TNT), ELECTRON-DENSITY, TESTOSTERONE, DERIVATIVES, INDEX, QSAR
  • Middle East Technical University Affiliated: No


Trinitrotoluene, known as TNT, is a widely used powerful explosive. It is a poisonous material, which injures almost all cells, especially those of liver, bone marrow, and kidney. Estrone is a sex hormone having an electron rich aromatic (phenolic) ring that is capable of forming a pi complex with molecules containing an electron deficient pi system. This study has focused on investigating the tendency of the complex formation of TNT with estrone. It has been thought that the formation of estrone-TNT pi complex might take place in a human body exposed to acute or prolong period of this hazardous chemical and consequently estrone activities might be impaired. The complex formation reaction was investigated mainly using DFT method with B3LYP/6-31G(d, p) basis set in gas phase. The existence of pi interaction between estrone and TNT was demonstrated by computational spectroscopic analyses (UV/Vis, IR, and H-1 NMR techniques). The frontier molecular orbital (HOMO and LUMO) analyses have shown that the considered pi complex is very resistant to oxidation with respect to its components, estrone and TNT.