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Proton Affinities of Didehydroporphyrin and Subporphyrin in Ground and Excited States Obtained by Quantum Chemical Calculations

Zoran Glasovac ; Laboratory for Physical Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
Mario Vazdar ; Laboratory for Physical Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
Davor Margetić ; Laboratory for Physical Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia

Puni tekst: engleski, pdf (2 MB) str. 63-70 preuzimanja: 652* citiraj
APA 6th Edition
Glasovac, Z., Vazdar, M. i Margetić, D. (2009). Proton Affinities of Didehydroporphyrin and Subporphyrin in Ground and Excited States Obtained by Quantum Chemical Calculations. Croatica Chemica Acta, 82 (1), 63-70. Preuzeto s https://hrcak.srce.hr/37979
MLA 8th Edition
Glasovac, Zoran, et al. "Proton Affinities of Didehydroporphyrin and Subporphyrin in Ground and Excited States Obtained by Quantum Chemical Calculations." Croatica Chemica Acta, vol. 82, br. 1, 2009, str. 63-70. https://hrcak.srce.hr/37979. Citirano 17.01.2020.
Chicago 17th Edition
Glasovac, Zoran, Mario Vazdar i Davor Margetić. "Proton Affinities of Didehydroporphyrin and Subporphyrin in Ground and Excited States Obtained by Quantum Chemical Calculations." Croatica Chemica Acta 82, br. 1 (2009): 63-70. https://hrcak.srce.hr/37979
Harvard
Glasovac, Z., Vazdar, M., i Margetić, D. (2009). 'Proton Affinities of Didehydroporphyrin and Subporphyrin in Ground and Excited States Obtained by Quantum Chemical Calculations', Croatica Chemica Acta, 82(1), str. 63-70. Preuzeto s: https://hrcak.srce.hr/37979 (Datum pristupa: 17.01.2020.)
Vancouver
Glasovac Z, Vazdar M, Margetić D. Proton Affinities of Didehydroporphyrin and Subporphyrin in Ground and Excited States Obtained by Quantum Chemical Calculations. Croatica Chemica Acta [Internet]. 2009 [pristupljeno 17.01.2020.];82(1):63-70. Dostupno na: https://hrcak.srce.hr/37979
IEEE
Z. Glasovac, M. Vazdar i D. Margetić, "Proton Affinities of Didehydroporphyrin and Subporphyrin in Ground and Excited States Obtained by Quantum Chemical Calculations", Croatica Chemica Acta, vol.82, br. 1, str. 63-70, 2009. [Online]. Dostupno na: https://hrcak.srce.hr/37979. [Citirano: 17.01.2020.]

Sažetak
Quantum-chemical calculations were used to investigate molecular and electronic properties of porphyrin and subporphyrin. Their basicities were estimated in ground and excited states. It was found
that multiple proton - nitrogen lone-pair coordination plays an important role in acid/base properties of the studied molecules. Lone pair-lone pair interactions in didehydroporphyrin and energetic stabilization of its protonated form lead to the increase of a proton affinity compared to porphyrin by 18 kcal mol−1. A planarization of the protonated (dehydroporphyrin) structure leads to the complete reversal of the π-electron ring currents indicating aromaticity of the protonated form. On the other hand, calculations indicate that subporphyrin is slightly (by 5 kcal mol−1) more basic than porphyrin, which was explained by non-planar geometry, imposed by smaller ring size.

Ključne riječi
DFT calculations; NICS; TDDFT; proton affinity; basicity

Hrčak ID: 37979

URI
https://hrcak.srce.hr/37979

Posjeta: 952 *