Supramolecular hydrogen-bonded networks in cytosinium nicotinate monohydrate and cytosinium isonicotinate cytosine dihydrate

Sridhar, Balasubramanian; Ravikumar, K.

doi:10.1107/s0108270110026430

Cited by 9 publications

(5 citation statements)

References 14 publications

(17 reference statements)

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“…3). This agrees with the value of 3.6353 (7) Å reported for cytosinium nicotinate monohydrate (Sridhar & Ravikumar, 2010).…”

Section: Resultssupporting

confidence: 92%

“…This type of interaction also resembles one in a previously reported structure, i.e. cytosinium nicotinate monohydrate (Sridhar & Ravikumar, 2010) (Fig. 2c).…”

Section: Resultssupporting

confidence: 88%

“…The carboxylate group is slightly twisted out of the plane of the pyridine ring to which it is attached [dihedral angle = 10.4 3]. This twist is close to the value reported in the crystal structure of cytosinium nicotinate monohydrate [dihedral angle = 9.6 (1) ; Sridhar & Ravikumar, 2010]. The dihedral angle between the CY and NA ions in (I) is 6.62 (11) .…”

Section: Resultssupporting

confidence: 73%

“…The title salts, namely, cytosinium 6-chloronicotinate monohydrate, (I), and 5-bromo-6-methylisocytosinium hydrogen sulfate, (II), have been investigated in order to to study the supramolecular architectures in the crystalline state. The crystal structures of cytosinium nicotinate monohydrate (Sridhar & Ravikumar, 2010), 2-amino-5-bromo-6methylpyrimidin-4(1H)-one 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one (1/1), the solvate 2-amino-5-bromo-6methylpyrimidin-4(1H)-one 2-amino-5-bromo-6-methylpyri- ISSN 2053ISSN -2296 # 2018 International Union of Crystallography midin-4(3H)-one N-methylpyrrolidin-2-one (1/1/1) and the partial cocrystal 2-amino-5-bromo-6-methylpyrimidin-4(3H)one 2-amino-5-bromo-6-methylpyrimidin-4(1H)-one 2-amino-6-chloropyrimidin-4(3H)-one (0.635/1/0.365) have also been reported (Gerhardt & Bolte, 2016).…”

Section: Introductionmentioning

confidence: 99%

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Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

et al. 2018

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Aminopyrimidine derivatives are biologically important as they are components of nucleic acids and drugs. The crystals of two new salts, namely cytosinium 6-chloronicotinate monohydrate, CHNO·CHClNO·HO, (I), and 5-bromo-6-methylisocytosinium hydrogen sulfate (or 2-amino-5-bromo-4-oxo-6-methylpyrimidinium hydrogen sulfate), CHBrNO·HSO, (II), have been prepared and characterized by single-crystal X-ray diffraction. The pyrimidine ring of both compounds is protonated at the imine N atom. In hydrated salt (I), the primary R(8) ring motif (supramolecular heterosynthon) is formed via a pair of N-H...O(carboxylate) hydrogen bonds. The cations, anions and water molecule are hydrogen bonded through N-H...O, N-H...N, O-H...O and C-H...O hydrogen bonds, forming R(8), R(7) and R(21) motifs, leading to a hydrogen-bonded supramolecular sheet structure. The supramolecular double sheet structure is formed via water-carboxylate O-H...O hydrogen bonds and π-π interactions between the anions and the cations. In salt (II), the hydrogen sulfate ions are linked via O-H...O hydrogen bonds to generate zigzag chains. The aminopyrimidinium cations are embedded between these zigzag chains. Each hydrogen sulfate ion bridges two cations via pairs of N-H...O hydrogen bonds and vice versa, generating two R(8) ring motifs (supramolecular heterosynthon). The cations also interact with one another via halogen-halogen (Br...Br) and halogen-oxygen (Br...O) interactions.

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“…3). This agrees with the value of 3.6353 (7) Å reported for cytosinium nicotinate monohydrate (Sridhar & Ravikumar, 2010).…”

Section: Resultssupporting

confidence: 92%

“…This type of interaction also resembles one in a previously reported structure, i.e. cytosinium nicotinate monohydrate (Sridhar & Ravikumar, 2010) (Fig. 2c).…”

Section: Resultssupporting

confidence: 88%

Section: Resultssupporting

confidence: 73%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

et al. 2018

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“…This cytosine-cytosine base pair (formed via three hydrogen bonds) is very similar to the protonated cytosine-neutral cytosine pair observed in many crystal structures (e.g. Das et al, 2010;Sridhar et al, 2010;Perumalla et al, 2005). Both these aspects are very interesting from a crystal engineering point of view .…”

Section: Structure Description Of [Znbr 2 (5fc)(h 2 O)]á(5fc) (Iii)supporting

confidence: 71%

Supramolecular architectures in metal(II) (Cd/Zn) halide/nitrate complexes of cytosine/5-fluorocytosine

2018

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Three new metal(II)-cytosine (Cy)/5-fluorocytosine (5FC) complexes, namely bis(4-amino-1,2-dihydropyrimidin-2-one-κN)diiodidocadmium(II) or bis(cytosine)diiodidocadmium(II), [CdI(CHNO)], (I), bis(4-amino-1,2-dihydropyrimidin-2-one-κN)bis(nitrato-κO,O')cadmium(II) or bis(cytosine)bis(nitrato)cadmium(II), [Cd(NO)(CHNO)], (II), and (6-amino-5-fluoro-1,2-dihydropyrimidin-2-one-κN)aquadibromidozinc(II)-6-amino-5-fluoro-1,2-dihydropyrimidin-2-one (1/1) or (6-amino-5-fluorocytosine)aquadibromidozinc(II)-4-amino-5-fluorocytosine (1/1), [ZnBr(CHFNO)(HO)]·CHFNO, (III), have been synthesized and characterized by single-crystal X-ray diffraction. In complex (I), the Cd ion is coordinated to two iodide ions and the endocyclic N atoms of the two cytosine molecules, leading to a distorted tetrahedral geometry. The structure is isotypic with [CdBr(CHNO)] [Muthiah et al. (2001). Acta Cryst. E57, m558-m560]. In compound (II), each of the two cytosine molecules coordinates to the Cd ion in a bidentate chelating mode via the endocyclic N atom and the O atom. Each of the two nitrate ions also coordinates in a bidentate chelating mode, forming a bicapped distorted octahedral geometry around cadmium. The typical interligand N-H...O hydrogen bond involving two cytosine molecules is also present. In compound (III), one zinc-coordinated 5FC ligand is cocrystallized with another uncoordinated 5FC molecule. The Zn atom coordinates to the N(1) atom (systematic numbering) of 5FC, displacing the proton to the N(3) position. This N(3)-H tautomer of 5FC mimics N(3)-protonated cytosine in forming a base pair (via three hydrogen bonds) with 5FC in the lattice, generating two fused R(8) motifs. The distorted tetrahedral geometry around zinc is completed by two bromide ions and a water molecule. The coordinated and nonccordinated 5FCs are stacked over one another along the a-axis direction, forming the rungs of a ladder motif, whereas Zn-Br bonds and N-H...Br hydrogen bonds form the rails of the ladder. The coordinated water molecules bridge the two types of 5FC molecules via O-H...O hydrogen bonds. The cytosine molecules are coordinated directly to the metal ion in each of the complexes and are hydrogen bonded to the bromide, iodide or nitrate ions. In compound (III), the uncoordinated 5FC molecule pairs with the coordinated 5FC ligand through three hydrogen bonds. The crystal structures are further stabilized by N-H...O, N-H...N, O-H...O, N-H...I and N-H...Br hydrogen bonds, and stacking interactions.

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Chiral Cobalt(III) Tris(1,2-diamine) Catalysts That Incorporate Nitrogenous Base Containing Anions for the Bifunctional Activation of Nucleophiles and Electrophiles in Enantioselective Addition Reactions

et al. 2021

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The lipophilic diastereomeric cobalt complexes Λ or Δ-[Co((S,S)-dpen) 3 ] 3+ 2Cl − BAr f − (Λ or Δ-(S,S)-− ) catalyze a number of enantioselective C−H bond addition reactions in the presence of aliphatic tertiary amines, but pyridine and N,N-dimethylaniline are much less effective. However, when these bases are incorporated into counter anions (4 − ) as in Λ or Δ-(S,S)-2 3+ 4 − Cl − BAr f − , highly enantioselective bifunctional catalysts can be realized. Salts of nicotinates, isonicotinates, related sulfonates, and N,N-dimethylaminobenzoate are effective. The 6-chloronicotinate salt gives slower rates and lower ee values, and the 6-aminonicotinate salt gives faster rates and higher ee values. The 6-methyl, 2-methoxy, and unsubstituted analogs afford intermediate results. The 6-aminonicotinate catalyst is applied to additions of dimethyl malonate to 14 arylsubstituted nitroolefins and additions of 6 1,3-dicarbonyl compounds to di-t-butyl azodicarboxylate, with average yields/ee values of 90%/85% and 94%/77%, respectively. The authors are unaware of other ionic catalysts for which Brønsted bases have been productively incorporated into the anions, which are seldom if ever purposefully functionalized in any manner.

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Supramolecular hydrogen-bonded networks in cytosinium nicotinate monohydrate and cytosinium isonicotinate cytosine dihydrate

Cited by 9 publications

References 14 publications

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

Supramolecular architectures in metal(II) (Cd/Zn) halide/nitrate complexes of cytosine/5-fluorocytosine

Chiral Cobalt(III) Tris(1,2-diamine) Catalysts That Incorporate Nitrogenous Base Containing Anions for the Bifunctional Activation of Nucleophiles and Electrophiles in Enantioselective Addition Reactions

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