Nitrilotriacetic acid, C6H9NO6

Skrzypczak‐Jankun, Ewa; Smith, D. A.; Małuszyńska, H.

doi:10.1107/s010827019400017x

Cited by 12 publications

(8 citation statements)

References 3 publications

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“…While the starting material 2,2,2-nitrilotriacetic acid [9,10] graphic threefold axis (C 3 symmetry) passing through the amine center, since the acetyl chloride moieties are all inequivalent. The C-N bond lengths are between 1.439(3) and 1.450(3)Å, slightly shorter compared to 2,2,2-nitrilotriacetic acid [10] and to a regular C-N single bond (1.469Å) [11]. This derives from the partial double bond character of the C-N bond, resulting to some extent in an iminium C-N=C resonance structure.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structure of 2,2,2- Nitrilotriacetyl Chloride with a Flat NC3 Pyramide

Klapötke

Krumm

Moll

2013

Zeitschrift Für Naturforschung B

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The reaction of 2,2,2-nitrilotriacetic acid with phosphorus pentachloride furnished 2,2,2-nitrilotriacetyl chloride (1), a useful chemical intermediate for various further reactions. The compound has been fully characterized by multinuclear NMR spectroscopy, vibrational analysis (IR and Raman), mass spectrometry and elemental analysis. Furthermore, the crystal structure of 1 has been determined and discussed thoroughly, showing a NC 3 unit with an unusual, nearly planar configuration.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Structure of 2,2,2- Nitrilotriacetyl Chloride with a Flat NC3 Pyramide

Klapötke

Krumm

Moll

2013

Zeitschrift Für Naturforschung B

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“…In the Cambridge Structural Database (CSD) 73 there are only two crystallographic structures of NTA 74,75 and they both are of the H 3 L form of the ligand; all crystallographic structures are marked with asterisks. Even though H 3 L * has no overall charge, it has two charged centers with opposite polarities, the positive one on the protonated N-atom and negative one on the de-protonated -COO Tables S5-S7).…”

Section: Resultsmentioning

confidence: 99%

Density Functional Theory and Isodesmic Reaction Based Prediction of Four Stepwise Protonation Constants, as log K_H⁽ⁿ⁾, for Nitrilotriacetic Acid. The Importance of a Kind and Protonated Form of a Reference Molecule Used

Govender

Cukrowski

2010

J. Phys. Chem. A

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An explicit application of isodesmic reaction (a proton exchange between the studied and similar in structure reference molecule), where the free energy change of the protonation reaction in water was obtained using the free energies in solution from a single continuum model, was used to predict stepwise protonation constants of nitrilotriacetic acid.Calculations were performed at the RB3LYP/6-311+G(d,p) level of theory in conjunction with PCM-UA0 solvation model. Five reference molecules were investigated. It has been established that one must pay a special attention to structural similarities between the studied and reference molecules and selection of a protonated form of the reference molecule. The protonation reactions in which the studied and reference molecule are involved in must be (if possible) of the same order; e.g. first (or generally nth) protonation reaction of the reference molecule must be used to compute the first (or nth) protonation constant of studied molecule. The lowest energy conformer must always be used. The first, second, third and fourth computed protonation constants differed, on average, from experimental values by 3.3, 0.8, 0.2 and 0.2 log units, respectively. It appears that the charge on the reference molecule has more decisive influence on accuracy of computed protonation constants than its structural differences when compared with the studied molecule. Results reported can be used as guide in constructing isodesmic reactions useful for the theoretical prediction of protonation constants by use of methodology described in this work.-2 -

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“…Such a situation is not quite surprising, considering the zwitterionic nature of uncomplexed H 3 NTA [12]. The ligand thus adopts a pseudo-C 3 point symmetry, with the three oxygen atoms pointing outwards bound to three different uranium atoms, giving a l 3 -1jO:2j O 0 :3jO 00 coordination mode.…”

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confidence: 91%

Uranyl ion complexation by the tripodal ligand nitrilotriacetate

Thuéry

2007

Inorganic Chemistry Communications

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Nitrilotriacetic acid, C6H9NO6

Cited by 12 publications

References 3 publications

Synthesis and Structure of 2,2,2- Nitrilotriacetyl Chloride with a Flat NC3 Pyramide

Synthesis and Structure of 2,2,2- Nitrilotriacetyl Chloride with a Flat NC3 Pyramide

Density Functional Theory and Isodesmic Reaction Based Prediction of Four Stepwise Protonation Constants, as log K_H⁽ⁿ⁾, for Nitrilotriacetic Acid. The Importance of a Kind and Protonated Form of a Reference Molecule Used

Uranyl ion complexation by the tripodal ligand nitrilotriacetate

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Nitrilotriacetic acid, C6H9NO6

Cited by 12 publications

References 3 publications

Synthesis and Structure of 2,2,2- Nitrilotriacetyl Chloride with a Flat NC3 Pyramide

Synthesis and Structure of 2,2,2- Nitrilotriacetyl Chloride with a Flat NC3 Pyramide

Density Functional Theory and Isodesmic Reaction Based Prediction of Four Stepwise Protonation Constants, as log KH(n), for Nitrilotriacetic Acid. The Importance of a Kind and Protonated Form of a Reference Molecule Used

Uranyl ion complexation by the tripodal ligand nitrilotriacetate

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Density Functional Theory and Isodesmic Reaction Based Prediction of Four Stepwise Protonation Constants, as log K_H⁽ⁿ⁾, for Nitrilotriacetic Acid. The Importance of a Kind and Protonated Form of a Reference Molecule Used