@conference{
author = "Mašulović, Aleksandra and Lađarević, Jelena and Radovanović, Lidija and Gak Simić, Kristina and Trišović, Nemanja and Rogan, Jelena and Mijin, Dušan",
year = "2021",
abstract = "Pažnja farmaceutske industrije u velikoj meri usmerena je na razumevanje sposobnosti
molekula vode da se inkorporiraju u kristalno pakovanje organskih molekula uspostavljanjem
različitih nekovalentnih intermolekulskih interakcija [1]. 2-Piridon je gradivna jedinica mnogih
supstanci koje poseduju antibakterijsku, antifungalnu, antiinflamatornu, antiviralnu i
antikancerogenu aktivnost [2]. U ovom radu, dva piridona, koja sadrže metil supstituisano
piridinsko jezgro u položajima 2,4 (2) i 3,5 (3) i
jedan piridon sa nesupstituisanim (1) piridinskim
jezgrom (slika), sintetisani su GuarešiTorpeovom reakcijom kondenzacije. Jedinjenja
su okarakterisana rendgenskom strukturnom
analizom kao i određivanjem tačke topljenja,
UV-Vis, FT-IR,
1H i
13C NMR spektroskopijom.
Asimetrične jedinice jedinjenja 1·2H2O i 3·2H2O
sastoje se od jednog molekula piridona i dva molekula vode, dok se u asimetričnoj jedinici
jedinjenja 2·4H2O nalaze četiri molekula vode. Inverzno orijentisani molekuli uspostavljaju N–
H···O vodonične veze i na taj način obrazuju (8) sintone. Tipovi vodenih kanala u supramolekulskoj arhitekturi zavise od prirode interakcija između dipol-jona. Dipol-dipol interakcije, jake i
slabe vodonične veze, π···π i C–H···π interakcije, određuju pakovanje ovih molekula, pri čemu
molekuli vode imaju značajnu ulogu.
Kristalografski podaci: 1·2H2O: C11H14N2O4, Mr = 238,24, trikliničan sistem, prostorna grupa P ,
a = 7,2258(14), b = 8,0470(16), c = 11,287(2) Å, α = 70,71(3), β = 74,88(3), γ = 79,85(3)°,
V = 595,1(2) Å3
, R1 = 0,0492; 2·4H2O: C13H22N2O6, Mr = 302,32, trikliničan sistem, prostorna
grupa P , a = 7,4411(15), b = 10,581(2), c = 11,235(2) Å, α = 108,96(3), β = 96,14(3),
γ = 107,41(3)°, V = 777,6(3) Å3
, R1 = 0,0443; 3·2H2O: C13H18N2O4, Mr = 266,29, trikliničan
sistem, prostorna grupa P , a = 7,5951(8), b = 9,0353(8), c = 11,5716(10) Å, α = 82,878(7), β =
72,010(8), γ = 71,919(9)°, V = 717,62(13) Å3
, R1 = 0,0522., The attention of pharmaceutical industry is set on understanding the ability of water molecules
to accompany organic crystals through interplay of various non-covalent intermolecular interactions [1]. 2-Pyridone is found as a structural
unit in many compounds with antibacterial,
antifungal, anti-inflammatory, antiviral or
anticancer activity [2]. In this paper, two
pyridone derivatives bearing methyl substituents in the pyridine unit in positions 2,4 (2)
and 3,5 (3) were synthesized via the Guareschi-Thorpe condensation as well as one
pyridone without substituents (1) in the
pyridine scaffold (Figure). These compounds were characterized by single-crystal X-ray analysis
as well as determination of the melting points, UV-Vis, FTIR,
1H and 13C NMR spectroscopy. The
asymmetric units of compounds 1·2H2O and 3·2H2O are comprised of one pyridone molecule and
two water molecules, whereas the asymmetric unit of compound 2·4H2O incorporates four water
molecules. Pairs of N–H···O hydrogen bonds connect inversion related molecules into the (8)
synthons in the supramolecular architectures. The type of water channel depends on the nature of
interactions established between zwitterions. Molecular packing is governed by dipole-dipole
interactions, strong and weak hydrogen bonds, π–π and C–H···π interactions, wherein water molecules play a significant role.
Crystal data: 1·2H2O: C11H14N2O4, Mr = 238.24, triclinic, space group P ,
a = 7.2258(14), b = 8.0470(16), c = 11.287(2) Å, α = 70.71(3), β = 74.88(3), γ = 79.85(3)°,
V = 595.1(2) Å3
, R1 = 0.0492; 2·4H2O: C13H22N2O6, Mr = 302.32, triclinic, space group P , a =
7.4411(15), b = 10.581(2), c = 11.235(2) Å, α = 108.96(3),
β = 96.14(3), γ = 107.41(3)°, V = 777.6(3) Å3
, R1 = 0.0443; 3·2H2O: C13H18N2O4,
Mr = 266.29, triclinic, space group P , a = 7.5951(8), b = 9.0353(8), c = 11.5716(10) Å, α =
82.878(7), β = 72.010(8), γ = 71.919(9)°, V = 717.62(13) Å3
, R1 = 0.0522.",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVII konferencija Srpskog kristalografskog društva, Kragujevac, 16–17. septembar 2021",
title = "SAMOORGANIZACIJA PAKOVANJA DIPOL-JON PIRIDONA PREKO MOLEKULA VODE, WATER ASSISTED ASSEMBLY OF PYRIDONE ZWITTERIONS",
pages = "11-10",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6709"
}