A Combined Experimental and Theoretical Study of Anion–π Interactions inN6‐ andN9‐Decyladenine Salts

Garcı́a-Raso, Ángel; Albertí, Francisca M.; Fiol, Juan J.; Lagos, Yolanda; Torres, Marta; Molins, Elı́es; Mata, Ignasi; Estarellas, Carolina; Frontera, Antonio; Quiñonero, David; Deyà, Pere M.

doi:10.1002/ejoc.201000436

Cited by 19 publications

(9 citation statements)

References 103 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A detailed description of this interaction, which involves the chloride anion and the six-membered ring of the adenine, is shown in Figure 4. The anion-π distances observed for 1-3 are similar to those previously reported for adenine derivatives and several anions like nitrate [26], chloride [27], HgCl…”

Section: D-h•••a 1 D(h•••a) D(d•••a)supporting

confidence: 86%

Cu(II)–N6-Alkyladenine Complexes: Synthesis, X-ray Characterization and Magnetic Properties

et al. 2018

Self Cite

View full text Add to dashboard Cite

Three new dinuclear copper(II) complexes [Cu 2 (µ-HL n) 2 (µ-Cl) 2 Cl 2 ]Cl 2 (1-3) have been synthesized and structurally characterized by single-crystal X-ray diffraction, where HL x , (HL 1 = N 6-propyladeninium, HL 2 = N 6-butyladeninium and HL 3 = N 6-isobutyladeninium) are N 6-alkyl bidentate NN donor adenine bases. Complexes 1-3 exhibit a coplanar arrangement of both N 6-alkyladeninium moieties with UD conformation, with the terms U(up) or D(down) referring to the coordination of each pyrimidinic N 3 atoms to the upper or lower metal center. In the three complexes, both copper atoms are five-coordinated (N 2 Cl 3 donor set), resembling a compressed trigonal bipyramid. Each adenine moiety is protonated in N 1 and the positive charge balanced by chloride counterions. Magnetic measurements of complexes 1 and 3 in the 2-300 K temperature range indicate antiferromagnetic coupling with J = −156.1(7) and J = −151(2) cm −1 , respectively. Density functional theory calculations have also been performed in order to estimate the exchange coupling constants in these complexes. The theoretically calculated J values are in good agreement with the experimental values.

show abstract

Section: D-h•••a 1 D(h•••a) D(d•••a)supporting

confidence: 86%

Cu(II)–N6-Alkyladenine Complexes: Synthesis, X-ray Characterization and Magnetic Properties

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…103 Frontera and co-workers synthesised the hydrochloride salts of N 9 -and N 6 -decyladenine 175 and 176, respectively, in order to investigate the influence of the substitution pattern on the formation of anion-p contacts. 104 The crystals structures of both salts reveal the presence of Cl À Á Á Áp interactions with N 6 -decyladenine 176 only (Fig. 25).…”

Section: Anion Recognition By Anion-p Interactionsmentioning

confidence: 98%

Anion receptor chemistry: highlights from 2010

2012

View full text Add to dashboard Cite

show abstract

“…There is only one example for a crystal structure with an N 6 -substituted adenine derivative protonated at N(7) and N(9), N 6 -decyladeninium chloride. 61 A building block found in all three supramolecular structures is the R2 2 (9) heterosynthon based on double H bonds between a protonated Hoogsteen site and a carboxylate group. Besides the R2 2 (9) heterosynthon, 1 contains an R2 2 (8) …”

Section: 9(2)° 21 ) While the C(4)-n(9)-c(8) C(2)-n(3)-c(4) Andmentioning

confidence: 99%

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine

McHugh

Erxleben

2011

Crystal Growth & Design

View full text Add to dashboard Cite

Co-crystal and salt formation of the kinetin analogue N 6 -benzyladenine with the pharmaceutically acceptable co-crystal and salt formers maleic acid, oxalic acid, glutaric acid, succinic acid, benzoic acid and fumaric acid has been studied by solid-state and solvent-drop grinding in combination with X-ray powder diffraction. In all cases salt or co-crystal formation was observed. Single crystals of (bzadeH + )(mal -) (1) and (bzadeH + )2(ox 2-) (2) were obtained by solution crystallization and the X-ray structures are reported along with that of (adeH + )2(mal -)2 . ade . 2H2O (3) (bzadeH + = N 6 -benzyladeninium, adeH + = adeninium, ade = adenine, mal -= hydrogen maleate, ox 2-= oxalate). The hydrogen-bonding motifs in 1 -3 are discussed. The salts contain a robust bzadeH + -carboxylate or ade-carboxylate R2 2 (9) heterosynthon involving the protonated Hoogsteen sites (N6-H, N7-H) of bzadeH + and ade. Molecular recognition between the protonated Hoogsteen site and the carboxylate group stabilizes the unusual 7H,9H tautomer of bzadeH + in 2 and the non-canonical 7H-adenine tautomer in 3.* To whom correspondence should be addressed. ABSTRACT Co-crystal and salt formation of the kinetin analogue N 6 -benzyladenine with the pharmaceutically acceptable co-crystal and salt formers maleic acid, oxalic acid, glutaric acid, succinic acid, benzoic acid and fumaric acid has been studied by solid-state and solvent-drop grinding in combination with X-ray powder diffraction. In all cases salt or co-crystal formation was observed. Single crystals of (bzadeH + )(mal -) (1) and (bzadeH + )2(ox 2-) (2) were obtained by solution crystallization and the X-ray structures are reported along with that of (adeH + )2(mal -)2 . ade . 2H2O (3) (bzadeH + = N 6 -benzyladeninium, adeH + = adeninium, ade = adenine, mal -= hydrogen maleate, ox 2-= oxalate). The hydrogen-bonding motifs in 1 -3 are discussed. The salts contain a robust bzadeH + -carboxylate or ade-carboxylate R2 2 (9) heterosynthon involving the protonated Hoogsteen sites (N6-H, N7-H) of bzadeH + and ade. Molecular recognition between the protonated Hoogsteen site and the carboxylate group stabilizes the unusual 7H,9H tautomer of bzadeH + in 2 and the non-canonical 7H-adenine tautomer in 3.3

show abstract

A Combined Experimental and Theoretical Study of Anion–π Interactions inN⁶‐ andN⁹‐Decyladenine Salts

Cited by 19 publications

References 103 publications

Cu(II)–N6-Alkyladenine Complexes: Synthesis, X-ray Characterization and Magnetic Properties

Cu(II)–N6-Alkyladenine Complexes: Synthesis, X-ray Characterization and Magnetic Properties

Anion receptor chemistry: highlights from 2010

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine

Contact Info

Product

Resources

About

A Combined Experimental and Theoretical Study of Anion–π Interactions inN6‐ andN9‐Decyladenine Salts

Cited by 19 publications

References 103 publications

Cu(II)–N6-Alkyladenine Complexes: Synthesis, X-ray Characterization and Magnetic Properties

Cu(II)–N6-Alkyladenine Complexes: Synthesis, X-ray Characterization and Magnetic Properties

Anion receptor chemistry: highlights from 2010

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N6-Substituted Adenine

Contact Info

Product

Resources

About

A Combined Experimental and Theoretical Study of Anion–π Interactions inN⁶‐ andN⁹‐Decyladenine Salts

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine