The co-crystallisation of pyridine with benzenepolycarboxylic acids: The interplay of strong and weak hydrogen bonding motifs

Dale, Sophie H.; Elsegood, Mark R. J.; Hemmings, Matthew; Wilkinson, Alexandra L.

doi:10.1039/b404563g

Cited by 100 publications

(53 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The weak (usually below 16 kJ/mol [21,22]) CHÁÁÁO [23][24][25], CHÁÁÁN [26,27], or CHÁÁÁp [28] interactions may also influence the geometry [29] of self-assembled molecules. The nonconventional CHÁÁÁO hydrogen bonds have been found in pyridine-carboxylic acid co-crystals [30][31][32][33], in crystals of N,N 0 -di(2-pyridyl)oxamide [34], and nitromethane entrapped in cyclodextrin [35]. It is commonly known that CH is a weaker hydrogen bond donor than NH/OH due to lower electronegativity of carbon than that of nitrogen and oxygen.…”

Section: Introductionmentioning

confidence: 99%

The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT, and AIM study

et al. 2013

View full text Add to dashboard Cite

The single crystal structures of two 2-acylaminopyrimidines, where alkyl groups in acyl moiety are iso-propyl (1) and dichloromethyl (2), were solved by X-ray diffraction method. The strength of intermolecular hydrogen bonding interactions depends on the C-H bond polarization increased by exchanging two methyl groups by chlorine atoms in the adjacent substituent. The computational methods provide an additional insight into the intermolecular interactions and are utilized in explaining the differences in the observed crystal structures. The experimental and computational data together explain the differences in the formed aggregates and revealed that these simple substitutions cause crucial changes in the intermolecular interactions.

show abstract

Section: Introductionmentioning

confidence: 99%

The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT, and AIM study

et al. 2013

View full text Add to dashboard Cite

show abstract

“…In the case of the co-crystals of 4,4 0 -bipyridine with di-and tricarboxylic acids, a zigzag chain structure is formed [4,20,21]. The existence of the intermolecular SÁÁÁO interaction causes this difference.…”

Section: Resultsmentioning

confidence: 90%

A two-dimensional ladder-type network in the 2:1 co-crystal of 1,2,5-thiadiazole-3,4-dicarboxylic acid and 4,4′-bipyridine

Tomura

Yamashita

2009

Struct Chem

View full text Add to dashboard Cite

The crystal structure of the 2:1 co-crystal of 1,2,5-thiadiazole-3,4-dicarboxylic acid and 4,4 0 -bipyridine, (C 4 H 2 N 2 O 4 S) 2 ÁC 10 H 8 N 2 , has been determined by X-ray diffraction at the monoclinic space group C2/c with cell parameters of a = 21.388 (7) Å , b = 6.735(2) Å , c = 14.877(5) Å , b = 110.431(3)°, and Z = 4. There are one molecule of thiadiazole and a half molecule of bipyridine in the asymmetric unit. The dihedral angle between the pyridine ring planes is 40.5(3)°. Two intramolecular O-HÁÁÁN [2.730(7) Å ] and O-HÁÁÁO [2.433(6) Å ] hydrogen bonds are observed in the thiadiazole molecule. In the crystal structure, the molecules form a unique twodimensional ladder-type network linked by intermolecular O-HÁÁÁN [2.704(4) Å ] hydrogen bonds and SÁÁÁO [3.100(5) Å ] heteroatom interactions.Keywords Two-dimensional ladder-type network Á 1, 2, 5-Thiadiazole Á 4, 4 0 -Bipyridine Á Intermolecular O-HÁÁÁN hydrogen bond Á Intermolecular SÁÁÁO heteroatom interaction

show abstract

“…37 The trimer unit was bonded forming three di- The infrared spectrum of II confirms also a deprotonation has occurred, with strong asymmetric and symmetric carboxylate absorptions at 1560 and 1398 cm -1 , respectively, which is similar to I and those previously reported. 36 In conclusion, it was found that 2,2'-biimidazole could spontaneously form supramolecular assemblies with benzoic acids, such as 5-sulfosalicylic acid and 3,4,5-trihydroxybenzoic acid by proton-transfer. Besides the hydrogen bonding interactions between the host and guest molecules, π-π stacking interactions also play an important role in the solid-state packing of these two complexes.…”

Section: Resultsmentioning

confidence: 98%

Supramolecular Assemblies in Salts of 2,2′‐Biimidazole with 5‐Sulfosalicylic Acid and 3,4,5‐Trihydroxybenzoic Acid

Li¹,

Yang²

2007

Chin. J. Chem.

View full text Add to dashboard Cite

Supramolecular assemblies of 2,2′‐biimidazole with 5‐sulfosalicylic acid and 3,4,5‐trihydroxybenzoic acid, have been synthesized and characterized by single‐crystal X‐ray diffraction methods. Both the two proton‐transfer compounds of 2,2′‐biimidazole with 3‐carboxy‐4‐hydroxybenzenesulfonic acid (5‐sulfosalicylic acid, 5‐SSA) [namely bis(2‐(2‐1H‐imidazolyl)‐1H‐imidazolium) 4‐hydroxybenzene‐3‐carboxylate‐1‐sulfonate monohydrate, 2(C6H7N4)+· C7H4O6S2−·H2O, (I)] and 3,4,5‐trihydroxybenzoic acid [namely 2,2′‐bi‐1H‐imidazolium bis(3,4,5‐trihydroxybenzoate) tetrahydrate, C6H8N42+·2(C7H5O5)−·4(H2O), (II)] feature extensively hydrogen‐bonded three‐dimensional network structures having significant interlayer π‐ π interactions between the cation and anion species. In I, a 5‐SSA2− dianionic species results from deprotonation of both the sulfonic and the carboxylic acid groups, all available O‐atom acceptors interact with all cation and water molecule donors by hydrogen bonds. In II, the formula unit displays a crystallographic inversion symmetry. The structural information about the two complexes between 2,2′‐biimidazole compound and benzenecarboxylic acids obtained in this work will be particularly important for the rational design of supramolecular organic functional materials.

show abstract

The co-crystallisation of pyridine with benzenepolycarboxylic acids: The interplay of strong and weak hydrogen bonding motifs

Cited by 100 publications

References 20 publications

The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT, and AIM study

The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT, and AIM study

A two-dimensional ladder-type network in the 2:1 co-crystal of 1,2,5-thiadiazole-3,4-dicarboxylic acid and 4,4′-bipyridine

Supramolecular Assemblies in Salts of 2,2′‐Biimidazole with 5‐Sulfosalicylic Acid and 3,4,5‐Trihydroxybenzoic Acid

Contact Info

Product

Resources

About