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U radu je sintetizovana serija 3-(4-supstituisanih benzil)-1,3-diazaspiro4.4nonan-2,4-diona čija je struktura određena temperaturama topljenja, FT-IR, 1H i 13C NMR i UV/Vis spektroskopijom. Uticaj supstituenata na apsorpcione spektre spirohidantoina, u različitim rastvaračima, proučavan je Hametovom jednačinom. Eksperimentalni rezultati su pokazali zadovoljavajuću saglasnost sa rezultatima kvantnohemijskih proračuna dobijenih primenom DFT metode. Pokazano je da supstituenti značajno utiču na intramolekulski transfer naelektrisanja (ICT) kao i na reaktivnost proučavanih hidantoina razmatranu na osnovu molekulskog elektrostatičkog potencijala (MEP)., In this work, a series of 3(4-substituted benzyl)-1,3-diazaspiro4.4nonane-2,4-dione was synthesized and fully characterized by melting points, FT-IR, 1H, and 13C NMR and UV/Vis spectroscopy. The Hammett equation was used to quantitatively evaluate the effects of substituents on the absorption frequencies in different solvents. The experimental results showed very good agreement with quantum chemical calculations obtained using DFT method. It was shown that substituents change the extent of conjugation, and affect intramolecular charge transfer (ICT) character. To estimate chemical reactivity of the molecules, the molecular electrostatic potential (MEP) surface maps were calculated for the optimized geometries of the investigated molecules.

U radu je sintetizovana serija 3-(4-supstituisanih benzil)-1,3-diazaspiro4.4nonan-2,4-diona čija je struktura određena temperaturama topljenja, FT-IR, 1H i 13C NMR i UV/Vis spektroskopijom. Uticaj supstituenata na apsorpcione spektre spirohidantoina, u različitim rastvaračima, proučavan je Hametovom jednačinom. Eksperimentalni rezultati su pokazali zadovoljavajuću saglasnost sa rezultatima kvantnohemijskih proračuna dobijenih primenom DFT metode. Pokazano je da supstituenti značajno utiču na intramolekulski transfer naelektrisanja (ICT) kao i na reaktivnost proučavanih hidantoina razmatranu na osnovu molekulskog elektrostatičkog potencijala (MEP)., In this work, a series of 3(4-substituted benzyl)-1,3-diazaspiro4.4nonane-2,4-dione was synthesized and fully characterized by melting points, FT-IR, 1H, and 13C NMR and UV/Vis spectroscopy. The Hammett equation was used to quantitatively evaluate the effects of substituents on the absorption frequencies in different solvents. The experimental results showed very good agreement with quantum chemical calculations obtained using DFT method. It was shown that substituents change the extent of conjugation, and affect intramolecular charge transfer (ICT) character. To estimate chemical reactivity of the molecules, the molecular electrostatic potential (MEP) surface maps were calculated for the optimized geometries of the investigated molecules.

U radu je sintetizovano dvadeset novih 3-(supstituisanih benzil)-5,5'-cikloalkan-spirohidantoina čija je struktura određena temperaturama toplenja, FT-IR, 1H i 13C NMR i UV spektroskopijom. Solvatohromizam ovih jedinjenja je proučavan metodom linearne korelacije energija solvatacije. Kvantitativna procena uticaja rastvarača na pomeranje apsorbcionih maksimuma je nedvosmisleno ukazala na vezu između lipofilnosti i relevantnih farmakoloških karakteristika proučavanih jedinjenja sa njihovim proton-akceptorskim svojstvima., In this work twenty novel 3-(substituted benzyl)-5,5'-cycloalkanespirohydantoins have been synthesized and fully characterized by melting point, FT-IR, 1H and 13C NMR and UV spectroscopy. Solvatochromism of these compounds have been analysed by means of linear solvation energy relationships (LSER) concept. The quantitative relationships beetwen hydrogen bonding interaction and the correspodenting pharmacologically relevant propereties of the studied compounds have been discussed.

U radu je sintetizovano dvadeset novih 3-(supstituisanih benzil)-5,5'-cikloalkan-spirohidantoina čija je struktura određena temperaturama toplenja, FT-IR, 1H i 13C NMR i UV spektroskopijom. Solvatohromizam ovih jedinjenja je proučavan metodom linearne korelacije energija solvatacije. Kvantitativna procena uticaja rastvarača na pomeranje apsorbcionih maksimuma je nedvosmisleno ukazala na vezu između lipofilnosti i relevantnih farmakoloških karakteristika proučavanih jedinjenja sa njihovim proton-akceptorskim svojstvima., In this work twenty novel 3-(substituted benzyl)-5,5'-cycloalkanespirohydantoins have been synthesized and fully characterized by melting point, FT-IR, 1H and 13C NMR and UV spectroscopy. Solvatochromism of these compounds have been analysed by means of linear solvation energy relationships (LSER) concept. The quantitative relationships beetwen hydrogen bonding interaction and the correspodenting pharmacologically relevant propereties of the studied compounds have been discussed.