@conference{
author = "Đorđević, Ivana and Janjić, Goran and Lazić, Anita and Gak, Kristina and Valentić, Nataša and Trišović, Nemanja and Radovanović, Lidija and Rogan, Jelena",
year = "2019",
abstract = "Nekovalentne interakcije imaju značajnu ulogu u formiranju supramolekulskog
kristalnog pakovanja molekula. Interakcije koje uključuju atome halogena obezbeđuju
slabo, ali visoko usmerenu kontrolu pakovanja molekula u čvrstom stanju. Uvođenje
F-atoma može dovesti do značajnih promena u 2D ili 3D strukturama [1], povećanja
stabilnosti biomolekula [2] ili poboljšanja dizajna lekova [3]. Da bi se ispitao efekat
supstitucije H-atoma F-atomom, sintetisana su i strukturno okarakterisana dva derivata
hidantoina: C15H16N2O3 (1) i C15H15N2O3F (2) (slika).
Analiza kristalnih pakovanja 1 i 2 pokazala je da su
NH…O i CH…O vodonične veze najbrojnije. U strukturi
2 se zbog fluorovanja povećava broj interakcija
cikloheksilnog (Ch) i fenil-grupe (Ph) prstena (CH…π
interakcije), kao i između dva Ph prstena (π-π
interakcije). Kvantno-hemijski proračuni na model
sistemima koji predstavljaju dimere derivata hidantoina
i izolovanih cikličnih jedinjenja, pokazali su da
fluorovanje utiče na stvaranje jačih CH…π i π-π
interakcija. Atom F u 2 učestvuje u formiranju tri
CH…F i jedne F…F interakcije, što je u saglasnosti sa
rezultatima Kembridžke baze podataka, koji su pokazali
da su najbrojnije CH…F i F…F interakcije, a njihova
jačina dostiže vrednost 2 kcal∙mol–1.
Kristalogafski podaci: 1, P–1, a = 6,3079(13),
b = 10,573(2), c = 11,415(2) Å, α = 67,21(3), β = 78,84(3),
γ = 76,16(3)°, R1 = 6,06%; 2, P–1, a = 5,9981(12), b =
11,148(2), c = 12,073(2) Å, α = 108,98(3), β = 101,57(3),
γ = 105,27(3)°, R1 = 4,82%., Non-covalent interactions have a significant role in supramolecular crystal packings
of the molecules. Halogen interactions provide weak but highly directed control of the
packing of molecules in the solid state. Introduction of F atom can leads to significant
differences in 2D or 3D structures [1], higher structural stability of biomolecules [2] or
improve drug design [3]. In order to examine the substitution effect of H atom with F
atom, two hydantoin derivatives were synthesized and structurally characterized:
C15H16N2O3 (1) i C15H15N2O3F (2) (Figure).
Crystallographic analysis of 1 and 2 showed that
NH…O and CH…O hydrogen bonds are the most numerous
in their crystal packings. Due to fluoridation in 2, the number of interactions among cyclohexyl (Ch) and phenyl ring
(Ph) rings (CH…π interactions), as well as among two Ph
rings (π-π interactions) is increased. Quantum-chemical
calculations on the model systems presented by dimmers
of hydantoin derivatives and isolated cyclic compounds,
verified that fluoridation caused the formation of stronger
CH…π and π-π interactions. The F atom in 2 is involved in
three CH…F and one F…F interactions, which is in agreement with the results from the Cambridge Structural Database, which have shown that CH…F and F…F interactions
are the most numerous, and their strength reaches the value
of 2 kcal∙mol–1.
Crystallographic data: 1, P–1, a = 6.3079(13),
b = 10.573(2), c = 11.415(2) Å, α = 67.21(3), β = 78.84(3),
γ = 76.16(3)°, R1 = 6.06%; 2, P–1, a = 5.9981(12),
b = 11.148(2), c = 12.073(2) Å, α = 108.98(3), β = 101.57(3), γ = 105.27(3)°, R1 = 4.82%.",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019",
title = "ULOGA NEKOVALENTNIH INTERAKCIJA FLUORA U PAKOVANJU MOTIVA: ANALIZA KRISTALOGRAFSKIH PODATAKA I KVANTNO-HEMIJSKI PRORAČUNI, THE ROLE OF NON-COVALENT FLUORINE INTERACTIONS IN PACKING MOTIFS: CRYSTALLOGRAPHIC DATA ANALYSIS AND QUANTUM CHEMICAL CALCULATIONS",
pages = "39-38",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6705"
}