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Safarowsky, Oliver; Windisch, B.; Mohry, André; Vögtle, Fritz

doi:10.1002/1521-3897(200006)342:5<437::aid-prac437>3.3.co;2-z

Cited by 18 publications

(30 citation statements)

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“…In 2000, Vögtle and coworkers [7] proposed a generic nomenclature system in which Schill's prefix was extended to include information about mechanical (mec) or covalent (cov) linkages within the components of the rotaxane to distinguish between intermolecular and intramolecular rotaxanes.…”

Section: Notementioning

confidence: 99%

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Nomenclature for rotaxanes and pseudorotaxanes (IUPAC Recommendations 2008)

Yerin¹,

Wilks²,

Moss

et al. 2008

Pure and Applied Chemistry

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Republication or reproduction of this report or its storage and/or dissemination by electronic means is Nomenclature for rotaxanes and pseudorotaxanes (IUPAC Recommendations 2008)Abstract: Expanded definitions of rotaxanes and pseudorotaxanes, their components, and other terms concerning rotaxanes are given. The uniform classification and nomenclature principles for naming different types of rotaxanes and pseudorotaxanes are described and illustrated with examples. Recommendations are provided for unambiguous description of rotaxane isomerism with special descriptors that include information about position of rotaxane components.

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Section: Notementioning

confidence: 99%

“…[7]. c Catenarotaxanes were formerly called "catrotanes" or "rotacatenanes" [7]. The designation [2rot-2cat-2rot]catenane was proposed according to the nomenclature system of Vögtle et al [7].…”

Section: Rot-3 Types Of Rotaxanesmentioning

confidence: 99%

Nomenclature for rotaxanes and pseudorotaxanes (IUPAC Recommendations 2008)

Yerin¹,

Wilks²,

Moss

et al. 2008

Pure and Applied Chemistry

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“…[7] For this purpose we treated the proven substrates 2,6-pyridinedicarboxylic acid dichloride 1 and diamine 2 [6] under dilution conditions (concentration 10 À3 mm) [5] in dichloromethane together with the auxiliary base triethylamine. This reaction gave besides 3 (yield 15 %) and 4 (yield 23 %) a colorless product in 20 % yield which had a molecular weight of m/z 2718.6 (MALDI-TOF-/FAB-MS), a melting point of > 325 8C, and an R f value [1] Evidence for the ten CH 3 COO À groups, assigned as lattice constituents, was strongly indicated by elemental analysis and IR spectroscopy, but it was not possible to locate these groups crystallographically due to a disorder problem.…”

Section: In Memory Of Eberhard Steckhanmentioning

confidence: 99%

A Molecular Knot with Twelve Amide Groups—One-Step Synthesis, Crystal Structure, Chirality

Safarowsky

Nieger

Fröhlich

et al. 2000

Angew. Chem. Int. Ed.

154

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Molecular knots are a little known class of substances. [1] Hitherto only some of the (historically first) phenanthroline type (Dietrich-Buchecker and Sauvage, 1989), [2] of the nucleic-acid type (Seeman, 1992), [3] and of the crown/quat type (Stoddart et al., 1997) [4] have been synthesized. We report here on probably the simplest synthesis of a new molecular trefoil knot in 20 % yield, which proceeds under self-organization. Besides a 96-membered araliphatic skeleton this knot only includes twelve CONH groups.In the course of the synthesis [5] of higher [n]catenanes [1] Ð with more than two interlacing wheelsÐwe planned to prepare larger amounts of macrocycle 4, [6] which should be favorable as a (ditopic) concave (host) template in the synthesis of [2]-and [3]catenanes. [7] For this purpose we treated the proven substrates 2,6-pyridinedicarboxylic acid dichloride 1 and diamine 2 [6] under dilution conditions (concentration 10 À3 mm) [5] in dichloromethane together with the auxiliary base triethylamine. This reaction gave besides 3 (yield 15 %) and 4 (yield 23 %) a colorless product in 20 % yield which had a molecular weight of m/z 2718.6 (MALDI-TOF-/FAB-MS), a melting point of > 325 8C, and an R f value [1] a) the ten CH 3 COO À groups, assigned as lattice constituents, was strongly indicated by elemental analysis and IR spectroscopy, but it was not possible to locate these groups crystallographically due to a disorder problem. It cannot be excluded that these groups are (at least partially) coordinated to the {(Mo)Mo 5 } pentagons, where many orientations are possible. The denomination ªKeplerateº, used in this paper for an anionic species, should be also used for neutral species when the topology of the system is in accordance with the definition (see ref.[1b]). [3] Crystal structure analysis of 2: H 492 C 24 Mo 102 O 534 ; M 19 114.06 g mol À1 , space group C2/c, a 44.586(1), b 26.365(1), c 44.565(1) , b 104.21(1)8, V 50 782 3 , Z 4, 1 2.500 g cm À3 , m 2.550 mm À1 , F(000) 36 768, crystal size 0.20 Â 0.08 Â 0.06 mm 3 . Crystals of 2 were removed from the mother liquor and immediately measured at 183(2) K on a Bruker axs SMART diffractometer (three-circle goniometer with a 1 K CCD detector, Mo Ka radiation, graphite monochromator; hemisphere of data collection at 0.38 wide w scans over three runs of 606, 435, and 230 frames (f 08, 888, 1808) from a 5.00 cm-distant detector). A total of 148 391 reflections (1.54 < V < 26.998) were collected, of which 54 698 unique reflections (R(int) 0.0811) were used. An empirical absorption correction on the basis of symmetry-equivalent reflections was performed with the SADABS program. The structure was solved and refined with the SHELXS-97 and SHELXL-97 programs (G. M. Sheldrick, University of Göttingen, 1997) to R 0.0713 for 23 929 reflections with I > 2s(I) and a max./ min. residual electron density of 2.816/ À 3.078 e À3 . Structure graphics were produced with the DIAMOND 2.1 program (K. Brandenburg, Crystal Impact GbR, 1999). Due to disorder, not all positions of the...

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“…Im Zuge von Synthesen [5] höherer [n]Catenane [1] ± mit mehr als zwei ineinander verschlungenen Reifen ± setzten wir die bereits bewährten Komponenten 2,6-Pyridindicarbonsäuredichlorid 1 und das Diamin 2 [6] unter Anwendung des Verdünnungsprinzips (Konzentration 10 À3 mm) [5] in Dichlormethan mit der Hilfsbase Triethylamin miteinander um, in der Absicht, den Makrocyclus 4 [6] in gröûeren Mengen zu erhalten; dieser sollte sich als (ditope) konkave (Wirt-)Schablone zur Synthese von [2]-und [3]Catenanen als günstig erweisen. [7] Angespornt durch das kürzlich gelungene Züchten von Kristallen unserer Amidcatenane und -rotaxane [8] versuchten wir auch hier das für die Templatwechselwirkung wichtige Wasserstoffbrückenbindungsmuster (im Kristall) als Voraussetzung für ergiebige Synthesen neuer mechanisch verknüpfter Aggregate [9] zu ergründen. Bei den nach mehrwöchiger Kristallisation aus Chloroform/Methanol erhaltenen Kristallen handelte es sich, wie die Kristallstrukturanalyse [10] Carbonylsauerstoffatome von I2 (I2-CO b ) bildet eine gegabelte Wasserstoffbrückenbindung zu den beiden Amidprotonen von P1 (303 bzw.…”

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“…[10] Die 1 H-NMR-Spektren von 5 sind signalreicher als diejenigen ähnlicher Catenane und Makrocyclen. [5,7,12] Für die bevorzugte Bildung des Knotens 5 gegenüber der Bildung eines möglichen topologisch isomeren Catenans oder eines nicht verknoteten topologisch isomeren Makromonocyclus (mit jeweils gleichfalls zwölf CONH-Gruppen) machen wir Wasserstoffbrückenbindungen zwischen Amidgruppen verantwortlich, ähnlich wie bei entsprechenden Templatsynthesen von Catenanen und Rotaxanen. [12,13] Dabei könnte aber anstelle des üblichen makrocyclischen Tetralactam-Wirts (des Typs 3) die mittlere Schleife des Knotens eine acyclische konkave Schablone für eine CONH-Gastgruppe bilden.…”

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Ein molekularer Knoten mit zwölf Amidgruppen – Einstufensynthese, Kristallstruktur, Chiralität

et al. 2000

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Molekulare Knoten sind eine noch wenig bekannte Substanzklasse. [1] Bisher konnten lediglich solche vom (historisch ersten) Phenanthrolin-(Dietrich-Buchecker und Sauvage, 1989), [2] Nucleinsäure- (Seeman, 1992) [3] und Krone/Quat-Typ (Stoddart et al., 1997) [4] synthetisiert werden. Wir berichten hier über die wohl einfachste, unter Selbstorganisation ablaufende Synthese eines neuartigen molekularen Kleeblattknotens in 20 % Ausbeute, der auûer einem 96-gliedrigen Die Einfachheit kovalent aufgebauter Modelle dieses Typs ermöglicht entsprechende Untersuchungen für die schnelle Charakterisierung neuer Metallkomplexe hinsichtlich ihrer Fähigkeit zur Funktionalisierung von C-H-Bindungen. Derzeit untersuchen wir Möglichkeiten zur vorhersagbaren Positionierung des Substrats am Metallzentrum durch nichtkovalente Wechselwirkungen, um so zu einer tatsächlich katalytisch aktiven oxidierenden Spezies zu gelangen.

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Cited by 18 publications

References 0 publications

Nomenclature for rotaxanes and pseudorotaxanes (IUPAC Recommendations 2008)

Nomenclature for rotaxanes and pseudorotaxanes (IUPAC Recommendations 2008)

A Molecular Knot with Twelve Amide Groups—One-Step Synthesis, Crystal Structure, Chirality

Ein molekularer Knoten mit zwölf Amidgruppen – Einstufensynthese, Kristallstruktur, Chiralität

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