Co-existence of water-mediated and normal base pairs in a supramolecular ribbon in 2-amino-4,6-dimethylpyrimidinium bromide 2-amino-4,6-dimethylpyrimidine monohydrate

Panneerselvam, Pathus; Muthiah, Packianathan Thomas; Francis, Savarimuthu

doi:10.1107/s1600536804007597

Cited by 15 publications

(18 citation statements)

References 10 publications

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“…The C2ÐN3ÐC4 angle at unprotonated atom N3 is 117.6 (1) , while for protonated atom N1 the C2ÐN1ÐC6 angle is 122.3 (1) . The geometry of the ampyH cation agrees with that of other ampyH cations reported in the literature (Panneerselvam et al, 2004). The SÐO distances lie in the range 1.447 (1)± 1.560 (1) A Ê , while the OÐSÐO angles range between 104.0 (1) and 113.3 (1) ( Table 1), indicating a distorted tetrahedral environment around the S atom.…”

Section: Commentsupporting

confidence: 82%

Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidinium hydrogen sulfate

et al. 2005

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In the title compound, C6H10N3+.HSO4-, the asymmetric unit consists of a hydrogen sulfate anion and a 2-amino-4,6-dimethylpyrimidinium cation. The hydrogen sulfate anions self-assemble through O-H...O hydrogen bonds, forming supramolecular chains along the b axis, while the organic cations form base pairs via N-H...N hydrogen bonds. The aminopyrimidinium cations join to the sulfate anions via a pair of hydrogen bonds donated from the pyrimidinium protonation site and from the exo amine group cis to the protonated site.

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Section: Commentsupporting

confidence: 82%

Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidinium hydrogen sulfate

et al. 2005

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“…In (II), one 2-amino-4,6dimethylpyrimidinium cation, one picolinate anion and one half-molecule of water (the O atom of the water molecule lies on a twofold axis) constitute the asymmetic unit. In both structures, the pyrimidine moieties are protonated at N1, leading to an increase in internal angles (see angles C2ÐN1Ð C6 in Tables 1 and 3) compared with neutral TMP (Koetzle & Williams, 1976) and AMPY (Panneerselvam et al, 2004). In (I), the dihedral angle between the pyrimidine and benzene rings is 76.06 (7) .…”

Section: Commentmentioning

confidence: 99%

Hydrogen-bonding patterns in trimethoprim picolinate and 2-amino-4,6-dimethylpyrimidinium picolinate hemihydrate

Hemamalini¹,

Muthiah²,

Lynch³

2006

Acta Crystallogr C

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In the title compounds, namely 2,4-diamino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-1-ium pyridine-2-carboxylate, C14H19N4O3+.C6H4NO2-, (I), and 2-amino-4,6-dimethylpyrimidin-1-ium pyridine-2-carboxylate hemihydrate, C6H10N3+.C6H4NO2-.0.5H2O, (II), the trimethoprim and 2-amino-4,6-dimethylpyrimidin-1-ium cations are protonated at one of the pyrimidine N atoms. In (I), bifurcated hydrogen bonds are observed between a picolinate O atom, the protonated N atom and the 2-amino group; the graph-set designator is R2(1)(6). The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N-H...N hydrogen bonds. In addition to the base pairing, one of the picolinate O atoms bridges the 2- and 4-amino groups on either side of the paired bases, resulting in a complementary DADA array. In (II), the carboxylate group of the picolinate anion binds with the protonated pyrimidine N atom and the 2-amino group of the pyrimidine moiety through a pair of N-H...O hydrogen bonds, leading to the common ring motif R2(2)(8). The water molecule, which resides on a twofold rotation axis, bridges the carboxylate group of the picolinate anion via O-H...O hydrogen bonds.

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“…The generation of R 4 2 (12) ring motifs involves water-mediated base pairs formed between AMPY (B) cations with symmetry-related O1W i [symmetry code: (i) Àx; 1 À y; Àz] molecules. The interaction is very much similar to water-mediated nucleobase pairs in biomolecules (Panneerselvam et al, 2004;Rozners & Moulder, 2004;Reddy et al, 2001;Morá vek et al, 2003). Thus, the interaction of two water molecules with AMPY cations A and B enables the formation of a discrete octameric unit along the c axis ( Fig.…”

Section: Crystal Structure Analysismentioning

confidence: 81%

Hydrogen bonding patterns in salts of derivatives of aminopyrimidine and thiobarbituric acid

Gomathi

Nirmalram

Muthiah

2015

Acta Crystallogr Sect B

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Three salts, namely 2-amino-4,6-dimethylpyrimidin-1-ium thiobarbiturate trihydrate (I), 2-amino-4,6-dimethoxypyrimidin-1-ium thiobarbiturate dihydrate (II) and 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidin-1-ium thiobarbiturate (III), were synthesized and characterized by IR and X-ray diffraction techniques. The primary interaction between the acid and base happens via N-H...O hydrogen bonds in (II) and (III), and via water-mediated N-H...OW and OW-HW...S in (I). The water molecules present in compound (I) form a (H2O)12 water cluster via water-water interactions. In all three compounds (I)-(III), thiobarbiturate anions form self-complementary pairs with a robust R2(2)(8) motif via a pair of N-H...O/N-H...S hydrogen bonds. They mimic the nucleobase base pairs by utilizing the same groups (thymine/uracil uses N3-H and C4=O8 groups during the formation of Watson-Crick and Hoogsteen base pairs with adenine). Compound (I) forms a water-mediated base pair through N-H...OW hydrogen bonds and forms an R4(2)(12) motif. The formation of N-H...S hydrogen bonds, water-mediated base pairs and water-water interactions in these crystal systems offers scope for these systems to be considered as a model in the study of hydration of nucleobases and water-mediated nucleobase base pairs in macromolecules.

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Co-existence of water-mediated and normal base pairs in a supramolecular ribbon in 2-amino-4,6-dimethylpyrimidinium bromide 2-amino-4,6-dimethylpyrimidine monohydrate

Cited by 15 publications

References 10 publications

Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidinium hydrogen sulfate

Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidinium hydrogen sulfate

Hydrogen-bonding patterns in trimethoprim picolinate and 2-amino-4,6-dimethylpyrimidinium picolinate hemihydrate

Hydrogen bonding patterns in salts of derivatives of aminopyrimidine and thiobarbituric acid

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