<b>Cyclononatetraenide. An Aromatic 10-π-Electron System</b>

LaLancette, E. A.; Benson, R. E.

doi:10.1021/ja00901a042

Cited by 79 publications

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“…L'accord entre le resultat thtorique et I'expCrience constitue donc dans ce cas, un test de la validit6 de la mCthode MNDO dans le domaine des composCs soufres insaturks. Signalons enfin, que aprbs optimisation complbte de la gComCtrie, la mCthode MNDO indique que les cycles de tous les composCs pentagonaux monocycliques pris en conc-c (C3C4): [3,4].…”

Section: Methodesunclassified

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Etude MNDO des composes conjugues enneagonaux

Ouamerali

Gayoso

1986

Int J of Quantum Chemistry

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ResumeSelon les r6sultat.s obtenus au moyen de MNDO, apds optimisation complkte de la gkomktrie, les anions cyclononatetrwnyle et benzocyclononatetranyle, l'ennkapyrrole et I'enneathiophkne sont des composks plans a tendance aromatique. L'enneafulvkne posskde une conformation pkferentielle plane mais une structure de composk conjugut polybnique alors que I'enneafuranne et le cyclononatetraene sont des molkcules gauches. La methode de Huckel universelle (MHU), qui est une technique emphique simple, tenant compte de tous les klectrons de valence et decrivant les systkmes u au moyen d'oM localis6es, conduit aux m h e s conclusions que la mkthode MNDO. Les calculs effectuks au moyen de MNDO et MHU nous ont permis de d6crire I'ensemble des propri6tks physicochimiques des composks conjuguks enneagonawt pris en considkration.A notre connaissance, nous prksentons ici, la premikre etude tkhrique des composks conjuguks contenant le cycle k neuf membres. AbstractWe present MNLKI calculations of a series of nine-membered conjugated compounds. The geometries have been fully optimized. Cyclononatetraenyl and benzocyclononatetraenyl anions, nonapyrrol, and nonathiophene appear to be planar aromatic compounds. Following MNDO, nonafulvene has a planar prefeted conformation, but a polyenic structure, while nonafuran and cyclononatetraene are gauche molecules. The Universal Huckel Method (UHM), a simple all valence electron empirical technique which describes u systems using localized MO, gives, qualitatively, the same results as the MNDO method. The quantum calculation carried out with MNDO and UHM have been used to describe the physicochemical properties of ninemembered ring conjugated compounds under consideration. To our knowledge, we present here the f i t theoretical study dealing with nine-membered conjugated molecules.

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Section: Methodesunclassified

“…La mtthode MNDO indique que l'anion cyclononatetraenyle et l'enneapyrrole sont des composts plans. La plantite de l'anion cyclononatetrabnyle s'accorde bien avec les rtsultats de l'ttude physicochimique rtaliste sur ce compost par Katz et Garrat [ 1,2] et par Lalancette et Benson [3,4].…”

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Etude MNDO des composes conjugues enneagonaux

Ouamerali

Gayoso

1986

Int J of Quantum Chemistry

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“…Oxidation of the tetraethylammonium salt of cyclononatetraneide anion in acetonitrile was suggested to be a oneelectron irreversible one (454).…”

Section: Amines Amino Acids and Derivatives Oxidation Of Nn-dimetmentioning

confidence: 99%

Organic Polarography

Pietrzyk¹

1966

Anal. Chem.

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HIS REVIEW covers articles which T have appeared in Chemical Abstracts and readily available journals during the two-year period ending November 1, 1965. As in the past, duplications and reinvestigations of previous work appear widely, and the tendency for authors to publish the same work in more than one journal has continued.This period has seen the publication of a special issue of Talanta honoring the 70th year for Professor Izaak If. Kolthoff (411). This issue is comprised entirely of invited contributions of his former students and associates and a list of Professor Kolthoff's past publications. Best wishes go to Professor Kolthoff for many more years of fruitful labor.Polarographic advances in Japan ( m 4 , 800, 801) and in Prague (429) were reviewed. The use of electron spin resonance spectrometry in evaluating electrode reactions in which free radicals are formed has continued t o grow (3, 25). Books dealing with "Polarography of Polymers'' (64) and "Organic Polarographic Analysis" (947) hare been published. Two books containing a listing of literature covering polarography through 1964 also became available (340,341 ) Yunierous reviews have appeared on the applications of polarography to pesticide analysis (98,224,226,524), lignin chemistry (627), cytostatically active compounds ($239, smoke analysis (700), proteins (114, 567,893), pharmaceuticals and drugs (1 74, 242, 249,329, 659,917), petroleum analysis (171 , 318,942), polymers (63), biocheniical analysis (661)) feed medicament analysis (9), clinical chemistry (104) , and enzyme activity (435). Other reviews have covered organic analysis (119,169,830,331) , organic polarography (496, 543, 583,773,805,897,914,946) and application to electrochemical synthesis (28.5) * Specialized polarographic reviews were concerned with alkaloids and their analysis (706), the effect of pH on halfwave potentials (176), utilization in assigning ring and chain structures and following the rate of tautomerism (344), polarography of enediols (log), substituted 3-phenyl-sydnones (767) , carbon disulfide and derivatives (639) and organic peroxides (269), the study of electron and proton transfer (6), the progress and problems in electrode kinetics (84) and the techniques for studying kinetics of oxidation (210).Reviews on adsorption of organic compounds at electrode surfaces (13, 218,443) and effect on reduction (493), a theoretical treatment of adsorption (136), and studies in adsorption isotherms (148) have appeared. Oscillographic and alternating current polarography were used to study the effects of anionic, cationic, and neutral surface active agents on polarographic analysis (337). Additional studies on adsorption are included under specific compounds.Studies in nonaqueous media have been reviewed (199,253,412). Other studies, however, mere concerned with the effects of different solvents on polarographic active compounds ($11, 71 9 ) .Work on the correlation of half-wave potentials with various constants continues. The relationship between halfwave potential...

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“…Einleitung. -Mit der Synthese von Cyclononatetraenid (1)3) entdeckten Kafz und Garratt [3] sowie LaLancette und Benson [4] 1963 nicht nur ein neues der Huckel-Regel [5] gehorchendes cyclisches 10 n-System, sondern auch ein Nucleophil, das sich mit Elektrophilen zu substituierten Cyclononatetraenen umsetzen lasst. Bei der systematischen Untersuchung der Reaktion stellten Boche et al [6] spater fest, dass bei der Umsetzung von 9-unti-Methoxybicyclo[6.1 .O]nona-2,4,6-trien (3, X = OCH,) mit Alkalimetallen nahezu ausschliesslich cis,cis,cis,trans -Cyclononatetraenid z4) entsteht.…”

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Synthese substituierter Cyclononatetraene

Sabbioni

Neuenschwander

1985

Helvetica Chimica Acta

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Synthesis of Substituted CyclononatetraenesIn the course of an exploration of possible synthetic pathways to nonafulvenes, a series of 1 -substituted cyclononatetraenes (CNT) 4b-1 have been prepared in yields of about 60 %. Their structures follow from spectroscopic data as well as from the quantitative valence isomerisation to 1-endo-substituted cis-3a,7a-dihydroindenes 8. Both all-cis-CNT-1 and cis,cis,cis,trans-CNT-2 have been used as nucleophiles. Whereas 2 is normally more nucleophilic than 1, the yield of cyclononatetraenes 4 prepared with 2 may be reduced due to by-products such as 9 and 10.

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Cyclononatetraenide. An Aromatic 10-π-Electron System

Cited by 79 publications

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Etude MNDO des composes conjugues enneagonaux

Etude MNDO des composes conjugues enneagonaux

Organic Polarography

Synthese substituierter Cyclononatetraene

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