DFT Investigations of Antioxidant Activity of Alizarin Red S
DFT ispitivanje antioksidativne aktivnosti alizarina Red S
Abstract
Density functional theory calculations were performed to evaluate the antioxidant activity of alizarin red S molecule. The conformational behavior of molecule were analysed at the M06-2X/6-311++G(d,p) method. The most stable conformer of alizarin red S has two IHBs. The expected antioxidant activity of alizarin red S was justified from ionization potential (IPs) and homolytic O-H bond dissociation enthalpy (BDEs) values. Heterolytic O-H bond cleavages (proton dissociation enthalpies, PDEs) were also computed. Calculated IP, BDE, and PA values suggested that one-step H atom transfer (HAT), rather than SPLET or SET-PT, would be the most favored mechanism for explaining the antioxidant activity of alizarin red S in gas phase. In aqueous solution all of three mechanisms were competitive.
Upotrebom DFT metode vršena su izračunavanja u cilju određivanja antioksidativne aktivnosti alizarina red S. Konformaciona priroda molekula analizirana ispitana je primenom M06-2X/6-311++G(d,p) metoda. Najstabilniji konformer alizarina red S ima dve unutrašnje vodonične veze. Očekivana antioksidativna aktivnost alizarina red S određena je izračunavanjem vrednosti jonizacionih potencijala (IP) i i vrednosti entalpija homolitičkog raskidanja O-H veza (BDE). Vrednosti entalpije heterolitičkog raskidanja O-H veza (entalpije disocijacije protona, PDE), su takođe izračunate. Izračunate IP, BDE i PA vrednosti ukazuju na to da je jednostepeni transfer H-atoma (HAT), pre nego SPLET ili SET-PT mehanizam, favorizovan u pogledu antioksidativne aktivnosti alizarina red S u gasnoj fazi. U vodenom rastvoru, sva tri mehanizma su konkurentna.
Keywords:
alizarin red S / DFT / antioxidativity / BDE / IP / antioksidativnostSource:
19. Savetovanje o biotehnologiji sa međunarodnim učešćem, Čačak, 07.- 08. 03. 2014., 2014Funding / projects:
- Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-172015)
- Multiscale Methods and Their Applicatios in Nanomedicine (RS-174028)
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Poljoprivredni fakultetTY - CONF AU - Marković, Zoran AU - Milenković, D AU - Djorović, J AU - Jeremić, S PY - 2014 UR - http://aspace.agrif.bg.ac.rs/handle/123456789/5567 AB - Density functional theory calculations were performed to evaluate the antioxidant activity of alizarin red S molecule. The conformational behavior of molecule were analysed at the M06-2X/6-311++G(d,p) method. The most stable conformer of alizarin red S has two IHBs. The expected antioxidant activity of alizarin red S was justified from ionization potential (IPs) and homolytic O-H bond dissociation enthalpy (BDEs) values. Heterolytic O-H bond cleavages (proton dissociation enthalpies, PDEs) were also computed. Calculated IP, BDE, and PA values suggested that one-step H atom transfer (HAT), rather than SPLET or SET-PT, would be the most favored mechanism for explaining the antioxidant activity of alizarin red S in gas phase. In aqueous solution all of three mechanisms were competitive. AB - Upotrebom DFT metode vršena su izračunavanja u cilju određivanja antioksidativne aktivnosti alizarina red S. Konformaciona priroda molekula analizirana ispitana je primenom M06-2X/6-311++G(d,p) metoda. Najstabilniji konformer alizarina red S ima dve unutrašnje vodonične veze. Očekivana antioksidativna aktivnost alizarina red S određena je izračunavanjem vrednosti jonizacionih potencijala (IP) i i vrednosti entalpija homolitičkog raskidanja O-H veza (BDE). Vrednosti entalpije heterolitičkog raskidanja O-H veza (entalpije disocijacije protona, PDE), su takođe izračunate. Izračunate IP, BDE i PA vrednosti ukazuju na to da je jednostepeni transfer H-atoma (HAT), pre nego SPLET ili SET-PT mehanizam, favorizovan u pogledu antioksidativne aktivnosti alizarina red S u gasnoj fazi. U vodenom rastvoru, sva tri mehanizma su konkurentna. C3 - 19. Savetovanje o biotehnologiji sa međunarodnim učešćem, Čačak, 07.- 08. 03. 2014. T1 - DFT Investigations of Antioxidant Activity of Alizarin Red S T1 - DFT ispitivanje antioksidativne aktivnosti alizarina Red S UR - https://hdl.handle.net/21.15107/rcub_agrospace_5567 ER -
@conference{ author = "Marković, Zoran and Milenković, D and Djorović, J and Jeremić, S", year = "2014", abstract = "Density functional theory calculations were performed to evaluate the antioxidant activity of alizarin red S molecule. The conformational behavior of molecule were analysed at the M06-2X/6-311++G(d,p) method. The most stable conformer of alizarin red S has two IHBs. The expected antioxidant activity of alizarin red S was justified from ionization potential (IPs) and homolytic O-H bond dissociation enthalpy (BDEs) values. Heterolytic O-H bond cleavages (proton dissociation enthalpies, PDEs) were also computed. Calculated IP, BDE, and PA values suggested that one-step H atom transfer (HAT), rather than SPLET or SET-PT, would be the most favored mechanism for explaining the antioxidant activity of alizarin red S in gas phase. In aqueous solution all of three mechanisms were competitive., Upotrebom DFT metode vršena su izračunavanja u cilju određivanja antioksidativne aktivnosti alizarina red S. Konformaciona priroda molekula analizirana ispitana je primenom M06-2X/6-311++G(d,p) metoda. Najstabilniji konformer alizarina red S ima dve unutrašnje vodonične veze. Očekivana antioksidativna aktivnost alizarina red S određena je izračunavanjem vrednosti jonizacionih potencijala (IP) i i vrednosti entalpija homolitičkog raskidanja O-H veza (BDE). Vrednosti entalpije heterolitičkog raskidanja O-H veza (entalpije disocijacije protona, PDE), su takođe izračunate. Izračunate IP, BDE i PA vrednosti ukazuju na to da je jednostepeni transfer H-atoma (HAT), pre nego SPLET ili SET-PT mehanizam, favorizovan u pogledu antioksidativne aktivnosti alizarina red S u gasnoj fazi. U vodenom rastvoru, sva tri mehanizma su konkurentna.", journal = "19. Savetovanje o biotehnologiji sa međunarodnim učešćem, Čačak, 07.- 08. 03. 2014.", title = "DFT Investigations of Antioxidant Activity of Alizarin Red S, DFT ispitivanje antioksidativne aktivnosti alizarina Red S", url = "https://hdl.handle.net/21.15107/rcub_agrospace_5567" }
Marković, Z., Milenković, D., Djorović, J.,& Jeremić, S.. (2014). DFT Investigations of Antioxidant Activity of Alizarin Red S. in 19. Savetovanje o biotehnologiji sa međunarodnim učešćem, Čačak, 07.- 08. 03. 2014.. https://hdl.handle.net/21.15107/rcub_agrospace_5567
Marković Z, Milenković D, Djorović J, Jeremić S. DFT Investigations of Antioxidant Activity of Alizarin Red S. in 19. Savetovanje o biotehnologiji sa međunarodnim učešćem, Čačak, 07.- 08. 03. 2014.. 2014;. https://hdl.handle.net/21.15107/rcub_agrospace_5567 .
Marković, Zoran, Milenković, D, Djorović, J, Jeremić, S, "DFT Investigations of Antioxidant Activity of Alizarin Red S" in 19. Savetovanje o biotehnologiji sa međunarodnim učešćem, Čačak, 07.- 08. 03. 2014. (2014), https://hdl.handle.net/21.15107/rcub_agrospace_5567 .