Structure of agmatine sulphate dihydrate: an extensive amine–sulphate–water hydrogen-bond network

Chandrasekhar, K.; Pattabhi, Vasantha; Raghunathan, S.

doi:10.1107/s0567740882009327

Cited by 7 publications

(6 citation statements)

References 4 publications

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“…In the literature, the structures of agmatine in the gas phase, under physiological conditions, and in the solid state were reported. , However, the analysis of the gas-phase and solution data is incomplete: (i) only one tautomeric form with the −NH–C(NH 2 )NH group and (ii) only all-extended conformations were considered for isolated and solvated free agmatine and its monoprotonated form. It was erroneously assumed that the monoprotonation of the guanidine functional group takes place at the amino nitrogen (NH 2 ) instead of the imino (NH) one.…”

Section: Push–pull Biomoleculesmentioning

confidence: 99%

Enhanced Basicity of Push–Pull Nitrogen Bases in the Gas Phase

2016

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Nitrogen bases containing one or more pushing amino-group(s) directly linked to a pulling cyano, imino, or phosphoimino group, as well as those in which the pushing and pulling moieties are separated by a conjugated spacer (C═X), where X is CH or N, display an exceptionally strong basicity. The n-π conjugation between the pushing and pulling groups in such systems lowers the basicity of the pushing amino-group(s) and increases the basicity of the pulling cyano, imino, or phosphoimino group. In the gas phase, most of the so-called push-pull nitrogen bases exhibit a very high basicity. This paper presents an analysis of the exceptional gas-phase basicity, mostly in terms of experimental data, in relation with structure and conjugation of various subfamilies of push-pull nitrogen bases: nitriles, azoles, azines, amidines, guanidines, vinamidines, biguanides, and phosphazenes. The strong basicity of biomolecules containing a push-pull nitrogen substructure, such as bioamines, amino acids, and peptides containing push-pull side chains, nucleobases, and their nucleosides and nucleotides, is also analyzed. Progress and perspectives of experimental determinations of GBs and PAs of highly basic compounds, termed as "superbases", are presented and benchmarked on the basis of theoretical calculations on existing or hypothetical molecules.

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Section: Push–pull Biomoleculesmentioning

confidence: 99%

Enhanced Basicity of Push–Pull Nitrogen Bases in the Gas Phase

2016

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“…This bication is in the gas-phase by 145 kJ/mol more stable (Table 2). The existence of bication II-H3 was also confirmed experimentally in the solid state in the form of its salt with sulphate [27]. The addition of a successive proton in the reaction II-H1 + H + ?…”

Section: Basicity Of Agmatine Speciesmentioning

confidence: 69%

“…The entire agmatine molecule is nearly planar. In this complex the imino and butylamino groups of agmatine are protonated [27].…”

Section: Molecular Structure Of the Agmatine Speciesmentioning

confidence: 99%

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Structure and stability of complexes of agmatine with some functional receptor residues of proteins

Remko

Broer

Remková

et al. 2017

Chemical Physics Letters

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“…Another example is agmatine sulfate dihydrate (BINWUQ) in which the hydrophobic fragment is about the width of a single water molecule giving rise to a one-dimensional chain, Figure 4. 38 Particularly striking is the structure of melemium sulfate dihydrate (MAYGEZ) in which the voids between the large, flat melemium cations are spanned by pairs of discrete water molecules that link sulfate anions together. The length correspondence between the…”

Section: Resultsmentioning

confidence: 99%

A Simple Strategy for Crystal Engineering Water Clusters

Sansam

Anderson

Steed

2007

Crystal Growth & Design

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We report the X-ray crystal structure of the protonated phenazine-2,3-diamine cation (3) salt (3)2SeO4·6H2O (4), which contains a discrete water decamer. This material is representative of a broad strategy to bring about the occurrence of solid-state water clusters in ionic structures by the combination of amphiphilic ions with large hydrophobic residues in combination with small, highly charged counterions. The strategy is illustrated by a wide range of examples taken from the Cambridge Structural Database (CSD).

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Structure of agmatine sulphate dihydrate: an extensive amine–sulphate–water hydrogen-bond network

Abstract: Abstract.CsHI4N4

Cited by 7 publications

References 4 publications

Enhanced Basicity of Push–Pull Nitrogen Bases in the Gas Phase

Enhanced Basicity of Push–Pull Nitrogen Bases in the Gas Phase

Structure and stability of complexes of agmatine with some functional receptor residues of proteins

A Simple Strategy for Crystal Engineering Water Clusters

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