Structure of<i>N,N</i>-dimethyl-1,4-phenylenediamine

Nakai, Hiroshi; Saito, Toshiaki; Yamakawa, Masumi

doi:10.1107/s0108270188001714

Cited by 2 publications

(2 citation statements)

References 2 publications

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“…This orientation allows partial alignment of the lone pairs of the NH 2 groups with the π-system but does not lead to intramolecular N–H···N interactions that are much shorter than the sum of the van der Waals radii of nitrogen and hydrogen. In both p -dication 8 and m -dication 9 , the average values of d C–C (1.393 and 1.392 Å, respectively), d C–N for the NH 2 groups (1.401 and 1.390 Å, respectively), and d C–N for the NH 3 + groups (1.443 and 1.462 Å, respectively) are all similar to those observed in related arylamines and their hydrochloride salts. − ,− …”

Section: Resultssupporting

confidence: 52%

“…Selected crystallographic data are summarized in Table , and representations of the structure are provided in Figure . As often observed in arylamines, − the NH 2 groups in BTA ( 1 ) are pyramidal, and the average sum of bond angles at nitrogen is 334.7°. The four atoms of nitrogen lie close to the average plane of the aromatic ring, and the two pairs of adjacent NH 2 groups are oriented in such a way that the two planes bisecting the angles H–N–H cut the average plane of the aromatic ring at angles of about 70°.…”

Section: Resultsmentioning

confidence: 99%

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Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Sosoe,

Malveau,

Maris

et al. 2023

J. Org. Chem.

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Like hydroquinones and quinones, aromatic compounds with multiple NH2 groups and the corresponding quinonediimines have the potential to serve as components of useful redox-active organic materials. Benzene-1,2,4,5-tetramine (BTA) and its oxidized form BTA-H2 offer a promising redox pair of this type, and the compounds have proven to be useful in many areas of chemistry. However, key aspects of their behavior have remained poorly studied, such as the nature of their protonated forms, their preferred molecular structures, their reactivity, and their organization in condensed phases. In the present work, we have used a combination of improved methods of synthesis, computation, spectroscopic studies, and structural analyses to develop a deeper understanding of BTA, BTA-H2, their salts, and related compounds. The new knowledge is expected to accelerate exploitation of the compounds in areas of materials science where desirable properties can only be attained by properly controlling the organization of molecular components.

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Section: Resultssupporting

confidence: 52%

Section: Resultsmentioning

confidence: 99%

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Sosoe,

Malveau,

Maris

et al. 2023

J. Org. Chem.

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Glassy Crystalline State and Water Sorption of Alkyl Maltosides

Kocherbitov

Söderman

2004

Langmuir

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A differential scanning calorimetric and sorption calorimetric study of two alkyl maltosides, C8G2 and C10G2, was performed. In the dry state, C8G2 and C10G2 do not form solid crystals but undergo a glass transition upon temperature change. The glass is partly ordered and has the same lamellar structure as the liquid crystals formed by the two maltosides. To reflect the presence of the glass transition and the structure, the terms “glassy crystals” and “glassy liquid crystals” can be used. A mechanism of the relaxation of the glassy crystals based on the results of small-angle X-ray scattering experiments is proposed. Experiments on water sorption showed that the glassy crystals turn into lyotropic liquid crystals upon sorption of water at constant temperature. This isothermal glass transition can be characterized by water content and change of partial molar enthalpy of mixing of water. A method to calculate the phase diagram liquid crystals−glassy liquid crystals is proposed.

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Structure ofN,N-dimethyl-1,4-phenylenediamine

Cited by 2 publications

References 2 publications

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Glassy Crystalline State and Water Sorption of Alkyl Maltosides

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