Supramolecular structure of unnatural nucleobases: Revised structure of (2:1) 6-methylisocytosinium dihydrogen monophosphate adduct

Portalone, Gustavo; Irrera, Simona

doi:10.1016/j.molstruc.2011.02.008

Cited by 19 publications

(21 citation statements)

References 41 publications

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“…1994), MECXUP (Tutughamiarso & Egert, 2012), MINVIP01 (Portalone & Irrera, 2011), OQURAU and OQUREY (Gerhardt et al, 2011), QOBCIV (Radhakrishnan et al, 2014) and ZERMIS (Toledo et al, 1995)]. The same kind of triple hydrogen-bond motif seen in Fig.…”

Section: Figurementioning

confidence: 69%

Two tautomeric forms of 2-amino-5,6-dimethylpyrimidin-4-one

2016

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Derivatives of 4-hydroxypyrimidine are an important class of biomolecules. These compounds can undergo keto-enol tautomerization in solution, though a search of the Cambridge Structural Database shows a strong bias toward the 3H-keto tautomer in the solid state. Recrystallization of 2-amino-5,6-dimethyl-4-hydroxypyrimidine, C6H9N3O, from aqueous solution yielded triclinic crystals of the 1H-keto tautomer, denoted form (I). Though not apparent in the X-ray data, the IR spectrum suggests that small amounts of the 4-hydroxy tautomer are also present in the crystal. Monoclinic crystals of form (II), comprised of a 1:1 ratio of both the 1H-keto and the 3H-keto tautomers, were obtained from aqueous solutions containing uric acid. Forms (I) and (II) exhibit one-dimensional and three-dimensional hydrogen-bonding motifs, respectively.

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Section: Figurementioning

confidence: 69%

Two tautomeric forms of 2-amino-5,6-dimethylpyrimidin-4-one

2016

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“…Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012). For some time now, we have studied proton-transfer adducts containing molecules of biological interest (Portalone, 2011a;Portalone & Irrera, 2011). In this context, benzamidine derivatives, which have shown strong biological and pharmacological activity (Powers & Harper, 1999), have been used in our group as bricks for supramolecular construction (Portalone, 2010(Portalone, , 2011b(Portalone, , 2012.…”

Section: Methodsmentioning

confidence: 99%

“…For the biological and pharmacological relevance of benzamidine, see: Powers & Harper (1999). For structural analysis of proton-transfer adducts containing molecules of biological interest, see : Portalone, (2011a); Portalone & Irrera (2011). For supramolecular association in proton-transfer adducts containing benzamidinium cations, see; Portalone (2010Portalone ( , 2011bPortalone ( , 2012; Irrera et al (2012); Irrera & Portalone (2012a,b,c).…”

Section: Related Literaturementioning

confidence: 99%

4-Methoxybenzamidinium hydrogen oxalate monohydrate

Irrera

Portalone

2012

Acta Cryst E

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The title hydrated salt, C8H11N2O+·C2HO4 −·H2O, was synthesized by a reaction of 4-methoxybenzamidine (4-amidinoanisole) and oxalic acid in water solution. In the cation, the amidinium group forms a dihedral angle of 15.60 (6)° with the mean plane of the benzene ring. In the crystal, each amidinium unit is bound to three acetate anions and one water molecule by six distinct N—H⋯O hydrogen bonds. The ion pairs of the asymmetric unit are joined by two N—H⋯O hydrogen bonds into ionic dimers in which the carbonyl O atom of the semi-oxalate anion acts as a bifurcated acceptor, thus generating an R 1 2(6) motif. These subunits are then joined through the remaining N—H⋯O hydrogen bonds to adjacent semi-oxalate anions into linear tetrameric chains running approximately along the b axis. The structure is stabilized by N—H⋯O and O—H⋯O intermolecular hydrogen bonds. The water molecule plays an important role in the cohesion and the stability of the crystal structure being involved in three hydrogen bonds connecting two semi-oxalate anions as donor and a benzamidinium cation as acceptor.

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“…For the biological and pharmacological relevance of benzamidine, see: Powers & Harper (1999); Grzesiak et al (2000). For structural analysis of proton-transfer adducts containing molecules of biological interest, see: Portalone (2011a); Portalone & Irrera (2011). For the supramolecular association in proton-transfer adducts containing benzamidinium cations, see: Portalone (2010Portalone ( , 2011bPortalone ( , 2012; ; .…”

Section: Related Literaturementioning

confidence: 99%

4-Methoxybenzamidinium hydrogen sulfate

Irrera¹,

Portalone²

2012

Acta Cryst E

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The title salt, C8H11N2O+·HSO4 −, has been synthesized by the reaction between 4-methoxybenzamidine and sulfuric acid. The asymmetric unit comprises a nonplanar 4-methoxybenzamidinium cation and one hydrogen sulfate anion. In the cation, the amidinium group has two identical C—N bonds [1.306 (2) and 1.308 (2) Å], and its plane forms a dihedral angle of 6.49 (8)° with the mean plane of the benzene ring. The ionic components are associated in the crystal via N—H+⋯O−, resulting in chains running approximately along the b-axis direction whicg are interconnected by O—H⋯O− hydrogen bonds.

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Supramolecular structure of unnatural nucleobases: Revised structure of (2:1) 6-methylisocytosinium dihydrogen monophosphate adduct

Cited by 19 publications

References 41 publications

Two tautomeric forms of 2-amino-5,6-dimethylpyrimidin-4-one

Two tautomeric forms of 2-amino-5,6-dimethylpyrimidin-4-one

4-Methoxybenzamidinium hydrogen oxalate monohydrate

4-Methoxybenzamidinium hydrogen sulfate

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