Synthesis and characterisation of unsymmetrical Schiff bases derived from 3,4-diaminopyridine. Crystal and molecular structure of hydrogen-bonded dimers of 3-{[(4-aminopyridin-3-yl)amino]methylene}pentane-2,4-dione

Opozda, Ewa M.; Łasocha, Wiesław; Włodarczyk-Gajda, Barbara

doi:10.1016/j.molstruc.2005.08.034

Cited by 12 publications

(7 citation statements)

References 38 publications

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“…Our search in Cambridge Crystal Structure Database [25] reveals several crystal structures containing the O-HÁÁÁN hydrogen bonds between hydroxyl group and pyridine moiety with orientation of hydroxyl group corresponding to the case of mixed O-HÁÁÁN/O-HÁÁÁp bonding [26][27][28][29][30][31]. In general, geometrical parameters of these bonds agree with results of our calculations (Table 2).…”

Section: Resultssupporting

confidence: 85%

Novel type of mixed O–H···N/O–H···π hydrogen bonds: monohydrate of pyridine

et al. 2009

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Investigation of characteristics of hydrogen bonding between pyridine and water by MP2/aug-cc-pvdz method reveals that these two molecules may form three types of hydrogen bonds depending on nature of proton withdrawal site of pyridine. Change of orientation of water with respect to plane of aromatic ring leads to transformation of the O-HÁÁÁN bond to O-HÁÁÁp bond via wide region of the potential energy surface where both lone pair of the nitrogen atom and p-system make significant contribution into hydrogen bonding. Hydrogen bond in this intermediate region may be considered as mixed O-HÁÁÁN/ O-HÁÁÁp bond representing new type of H bonds.

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Section: Resultssupporting

confidence: 85%

Novel type of mixed O–H···N/O–H···π hydrogen bonds: monohydrate of pyridine

et al. 2009

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“…Schiff bases derived from o-hydroxyaromatic aldehydes and ketones are excellent models for the study of ketoenol tautomerism both in solution and in the solid state [59][60][61][62][63][64][65][66]. During the past decade such Schiff bases started drawing attention due to their physical properties in the crystalline state [67][68][69][70][71][72][73][74][75][76][77][78]. These properties are greatly influenced by the topochemistry of the Schiff base molecules which in turn is highly affected by the crystal structure.…”

Section: These Schiff Base Ligands May Act As Bidentate No- Tridentmentioning

confidence: 99%

Schiff bases derived from hydroxyaryl aldehydes: molecular and crystal structure, tautomerism, quinoid effect, coordination compounds

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Cinčić

Friščić

et al. 2010

Maced. J. Chem. Chem. Eng.

105

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During the last 50 years a vast number of structural studies on Schiff bases derived from hydroxyaryl aldehydes and their coordination compounds have been undertaken. In this review we present a systematic and brief overview of the most important discoveries and achievements accomplished in this field. The occurrence of Schiff bases (and their complexes) derived from nine most commonly used hydroxyaryl aldehydes in the Cambridge Structural Database (CSD) has been investigated. Keto-enol tautomerism and intramolecular hydrogen bonding in salicylaldimines and naphthaldimines is discussed, with a comment of the most common errors in determining the correct tautomeric form. Also, the interrelationship of crystal packing and the substituents on the Schiff base is studied. Finally, we give a short overview of conformational differences between free Schiff bases and Schiff bases bonded to metal ions as well as some structural characteristics of Schiff base metal complexes.

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“…Comment 3,4-Diaminopyridine, (I), has been used as an amine component in Schiff base reactions (Opozda et al, 2006). In this contribution, we report the crystal and molecular structure of the compound itself.…”

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confidence: 99%