Organic salts formed by 2,4,6-triaminopyrimidine and selected carboxylic acids via a variety of hydrogen bonds: Synthons cooperation, and crystal structures

Xing, Peiqi; Li, Qingyun; Li, Yingying; Wang, Kunpeng; Zhang, Qi; Wang, Lei

doi:10.1016/j.molstruc.2017.01.066

Cited by 20 publications

(4 citation statements)

References 29 publications

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“…Analyzing the geometries of the N-H•••O hydrogen bonds dominating in this structure, we see that the donor•••acceptor distances are in the wide range from 2.684(3) to 3.028(3) Å and are significantly shortened compared to those observed in co-crystals 1-3 (Table 2). Shortening the bond length is due to hydrogen proton transfer between the adjacent components, and the same phenomenon is observed with other salts of 2,4,6-TAP [29,32]…”

Section: Co-crystal Formed Between 5-ap and Hbta (2)supporting

confidence: 66%

“…In 78.3% of the published cases (Figure 2B), 2,4,6-TAP agents interact with carboxylic co-formers mostly by accepting the acidic proton by the N-heterocyclic nitrogen atom and becoming the 2,4,6-TAP + cation. The 2,4,6-TAP + residues in these crystals are always sustained with complementary carboxylates via the charge-assisted N + -H•••O − and multiple N-H•••O − H-bonds giving the supramolecular conglomerates in the form of salt solvates/hydrates (CSD refcode: CALVES [8,9], EPUQAK [25], GIFWOL [26], KEVLUV [27], KOCJAR [28], KOCHIX [28], KOCHOD [28], VEXQEX [29], VEXQOH [29], VEXQUN [29], VEQZOQ [29], VEXZUW [29], and VEYBAF [29]) and salts (CSD refcode: DARMIV [30], TESRAM [31], VEYBEJ [29], VIPZUS [8,9], and YUKVAE [32]). The 2,4,6-TAP also interacts with the acidic components only by the neutral O-H•••N/N-H•••O H-bonds, confirming the lack of proton transfer from the carboxylic unit to the 2,4,6-TAP entity (Figure 2B).…”

Section: Introductionmentioning

confidence: 99%

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Neutral and Ionic Form of (Benzylthio)Acetic Acid in Novel Aminopyrimidine Based Multi-Component Crystalline Phases

Sienkiewicz-Gromiuk,

Drzewiecka-Antonik

2023

Crystals

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(benzylthio)acetic acid (HBTA) and some aminopyrimidines, namely 2-aminopyrimidine (2-AP), 5-aminopyrimidine (5-AP), 2-amino-4,6-dimethylpyrimidine (2-A-4,6-DMP), and 2,4,6-triaminopyrimidine (2,4,6-TAP), were successfully embodied as structural units into the construction of a total of four novel supramolecular organic frameworks. The received crystalline solids were inspected by single-crystal X-ray diffraction (SC XRD) in order to obtain insight into the structural and supramolecular facets. The SOFs deriving from 2-AP, 5-AP, and 2-A-4,6-DMP crystallize in the form of co-crystals (1–3), while the one originating from 2,4,6-TAP crystallizes as a salt solvate (4). The SC XRD results indicated the different contents of structural residues present in the asymmetric units of the crystals 1–4 despite using the same molar ratio of molecular co-former components in each case. The molecular structures of co-crystals 1–3 consist of either one neutral residue of each starting component (1 and 3) or one nonionized residue of the aminopyrimidine ingredient and two neutral residues of the acidic component (2). The asymmetric unit of salt solvate 4 is composed of two ionized residues of each co-former (two 2,4,6-TAP+ cations and two BTA− anions) and one MeOH solvent molecule. The most extensive H-bonding network is observed in the crystal structure of salt solvate 4. The relevant molecular ingredients in co-crystals 1–3 are mainly held together by the neutral Ocarboxylic–H···Npyrimidine and Namine–H···Ocarboxylic H-bonds. In the case of aggregate 4, the corresponding ionic residues are predominantly sustained by the charged-assisted Npyrimidinium–H···Ocarboxylate and Namine–H···Ocarboxylate hydrogen interactions. The MeOH solvent, incorporated into the crystal lattice of adduct 4, is also involved in H-bonding by simultaneously serving as the single donor in OMeOH–H···S and the single acceptor in Namine–H···OMeOH H-bonds, which afforded the structural diversity within the 2,4,6-TAP+ cations and BTA− anions. Other weaker sets of additional non-covalent contacts existing in the crystal structures of analyzed conglomerates are involved in the self-assembly, stabilization, and expansion of total supramolecular organic frameworks. The fact of the formation of non-covalent bonded supramolecular organic frameworks in question is also reflected in corresponding results obtained through elemental analysis (EA), Fourier transform infrared spectroscopy (FT–IR), and thermal analysis (TG/DSC).

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Section: Co-crystal Formed Between 5-ap and Hbta (2)supporting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Neutral and Ionic Form of (Benzylthio)Acetic Acid in Novel Aminopyrimidine Based Multi-Component Crystalline Phases

Sienkiewicz-Gromiuk,

Drzewiecka-Antonik

2023

Crystals

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“…2,4,6-Triaminopyrimidine is an interesting and challenging molecule due to its multiple hydrogen-bond donors and acceptors. The crystal structures of the following salts of 2,4,6-triaminopyrimidine (Schwalbe & Williams, 1982) have been reported in the literature: 2,4,6-triaminopyrimidinium (TAP + ) dichloride dihydrate (Portalone & Colapietro, 2007), TAP + malonate, TAP + succinate, TAP + glutarate, TAP + adipate, TAP + thiodipropionate (Pedireddi et al, 1998), TAP zidovudine (Bhatt et al, 2009), TAP + barbiturate (Marchi-Artzner et al, 1998), TAP + sulfate pentahydrate (Nimthong et al, 2013), TAP + 3,5-dihydroxybenzoate dihydrate, TAP + 3-nitrophthalate monohydrate, TAP + 5-amino-2,4,6-triiodoisophthalate dihydrate, TAP + 2,5-dibromoterephthalate dihydrate, TAP + naphthalene-1,5-disulfonate, TAP + sebacicate, TAP + 1,2,4benzenetricarboxylate monohydrate, TAP + biphenyl-2,2 0 ,5,5 0tetracarboxylate monohydrate (Xing et al, 2017) and 2,4,6triamnipyrimidinium 3-nitrobenzoate (Mohana et al, 2023). Dicarboxylic acids have good potential for use as proton donors in the synthesis of proton-transfer compounds.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular interactions in some organic hydrated 2,4,6-triaminopyrimidinium carboxylate and sulfate salts

Sangavi,

Kumaraguru,

McMillen

et al. 2023

Acta Crystallogr C

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Four salts, namely, 2,4,6-triaminopyrimidinium 6-chloronicotinate dihydrate, C4H8N5 +·C6H3ClNO2 −·2H2O, (I), 2,4,6-triaminopyrimidinediium pyridine-2,6-dicarboxylate dihydrate, C4H9N5 2+·C7H3NO4 2−·2H2O, (II), 2,4,6-triaminopyrimidinediium sulfate monohydrate, C4H9N5 2+·SO4 2−·H2O, (III), and 2,4,6-triaminopyrimidinium 3,5-dinitrobenzoate dihydrate, C4H8N5 +·C7H3N2O6 −·2H2O, (IV), were synthesized and characterized by X-ray diffraction techniques. Proton transfer from the corresponding acid to the pyrimidine base has occurred in all four crystal structures. Of the four salts, two [(I) and (IV)] exist as monoprotonated bases and two [(II) and (III)] exist as diprotonated bases. In all four crystal structures, the acid interacts with the pyrimidine base through N—H...O hydrogen bonds, generating an R 2 2(8) ring motif. The sulfate group mimics the role of the carboxylate anions. The water molecules present in compounds (I)–(IV) form water-mediated large ring motifs. The formation of water-mediated interactions in these crystal structures can be used as a model in the study of the hydration of nucleobases. Water molecules play an important role in building supramolecular structures. In addition to these strong hydrogen-bonding interactions, some of the crystal structures are further enriched by aromatic π–π stacking interactions [(I) and (II)].

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“…31 Pyrimidine derivatives can form strong intermolecular structures by using hydrogen bonds. 32 Conventionally, it can increase the shelf life of polymeric materials by preventing aging by photooxidation, using two important classes of light stabilizers—benzophenone and benzotriazole. 33…”

Section: Introductionmentioning

confidence: 99%

The effects of the inclusion of 1,2,4-triazole derivatives into the main chains of the polyurethane urea exposed to UV radiation

Oprea¹,

Potolinca²

2021

High Performance Polymers

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Linear polyurethane urea containing 1,2,4-triazole segments was obtained by polyaddition of the 3,5-diamino-1,2,4-triazole (DATA) to urethane prepolymer. Also, three crosslinked polymers with different crosslinkers (2,4,6-triaminopyrimidine (TAP), glycerin (Gly), castor oil (CO)) were synthesized. Thermogravimetric analysis, of the obtained polymers, indicated good thermal stability up to 310°C. The polyurethane urea chemical structure was confirmed by FTIR analysis. The glass transition temperatures (Tg) of these polymers, measured by differential scanning calorimetry (DSC), were found in the range of −52°C to −56°C. These values were not significantly influenced by the structure of the hard domain and the intermolecular interactions. The tensile testing showed that the inclusion of 1,2,4-triazole in polyurethane structure substantially improves the tensile strength up to 58 MPa. The obtained polyurethane urea presents surface slight hydrophobic and low interfacial tension. The positive effect of the 1,2,4-triazole segment from the polymer main chain in the UV aging process of these polymer materials has been studied. After exposure to UV radiation, few changes were observed in the molecular structure, in the surface morphology and the mechanical properties.

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Organic salts formed by 2,4,6-triaminopyrimidine and selected carboxylic acids via a variety of hydrogen bonds: Synthons cooperation, and crystal structures

Cited by 20 publications

References 29 publications

Neutral and Ionic Form of (Benzylthio)Acetic Acid in Novel Aminopyrimidine Based Multi-Component Crystalline Phases

Neutral and Ionic Form of (Benzylthio)Acetic Acid in Novel Aminopyrimidine Based Multi-Component Crystalline Phases

Supramolecular interactions in some organic hydrated 2,4,6-triaminopyrimidinium carboxylate and sulfate salts

The effects of the inclusion of 1,2,4-triazole derivatives into the main chains of the polyurethane urea exposed to UV radiation

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