Microcrystalline solid–solid transformations of conformationally-responsive solvates, desolvates and a salt of <i>N</i>,<i>N</i>′-(1,4-phenylene)dioxalamic acid: the energetics of hydrogen bonding and n/π → π* interactions

The use of tris(4-aminophenyl)amine (TAPA) as central to the synthesis of both polyimines and polyimides and covalent organic frameworks and inorganic cages, among others, has grown in the last few years. The resulting materials exhibit high performance in their area of application. In this contribution, the crystal structures of two TAPA derivatives, triethyl (nitrilotris(benzene-4,1-diyl))tricarbamate (1) and triethyl 2,2′,2″-((nitrilotris(benzene-4,1-diyl))tris(azanediyl))tris(2-oxoacetate) (2), are described. The molecular and supramolecular structures of both compounds were compared between them and with analogous compounds. The analyses of their vibrational and 13C-CPMAS NMR spectroscopies, as well as their thermal stability, were included and corelated with the crystal structure. Hirshfeld surface analysis on the crystal structures of both TAPA derivatives revealed the stabilization of the crystal network via the amide N—H∙∙∙O interactions of dispersive nature in the carbamate, whereas dispersive carbonyl–carbonyl interactions also played a competitive role in the supramolecular arrangement of the oxamate. Interaction energy DFT calculations performed at the B3LYP/6-31G(d,p) level allowed us to estimate the energy contributions and nature of several interactions in terms of the stability of both crystal lattices.

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Microcrystalline solid–solid transformations of conformationally-responsive solvates, desolvates and a salt of N,N′-(1,4-phenylene)dioxalamic acid: the energetics of hydrogen bonding and n/π → π* interactions

Abstract: The supramolecular structures of H2pOx·2S (S = DMSO, DMF, ⅓(MeOH·2W), W) solvates were stablished. The energetics of amide N–H⋯O and n/π → π* interactions maintain the crystal network and the reversibility between polymorphs.

Cited by 2 publications

References 80 publications

Oxamate-based potassium–organic assembly with the uncommon binodal (6,12)-coordinated alb topology

Oxamate-based potassium–organic assembly with the uncommon binodal (6,12)-coordinated alb topology

Crystal Structure, Supramolecular Organization, Hirshfeld Analysis, Interaction Energy, and Spectroscopy of Two Tris(4-aminophenyl)amine-Based Derivatives

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