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Some symmetrical halogen and methoxy exchange reactions in aromatic systems; Quelques reactions symetriques d'echanges d'halogenes et de groupes methoxyles dans les composes aromatiques; Simmetricheskie reaktsii s galoidnym i metoksidnym obmenom v aromaticheskikh sistemakh; Algunas reacciones simetricas de intercambio de halogenos y grupos metoxilo en compuestos aromaticos

Conference:

Abstract

Isotope tracers are essential in the study of the kinetics of symmetrical nucleophilic substitution reactions at an aromatic carbon atom. The iodine exchange between iodo-nitro-aromatic compounds and iodide ions in acetone or methanol solution has been studied both qualitatively and quantitatively by labelling the iodide ions with iodine-131. The reaction mixture is sampled at convenient time intervals, the two reactants separated by toluene-water extraction, and the progress of the reaction ascertained by beta-counting with a liquid Geiger counter. Measurements have been extended to 'carrier-free' concentrations of iodide ions. The preparation of certain nitro-methoxy-aromatic compounds, labelled with carbon-14 in the methoxy group, is described. Symmetrical methoxy exchange reactions of these compounds with methoxide ions, in methanol solution, have been studied. After separation of the reactants (from samples of the reaction mixture taken at convenient time intervals) by toluene-water extraction, the aromatic compounds are recovered and then specific activities determined by beta-scintillation counting with a plastic phosphor. In the discussion of the experimental data, special attention is paid to the effect of ionic strength on the specific rate of the reaction. Comparison is made with ionic strength effects observed in symmetrical biomolecular nucleophilic reactions at a saturated (aliphatic) carbon atom, and reference  More>>
Authors:
Broadbank, R W.C.; Harhash, A H.E.; Kanchanalai, S [1] 
  1. Leicester College of Technology and Commerce, Leicester (United Kingdom)
Publication Date:
Mar 15, 1962
Product Type:
Conference
Resource Relation:
Conference: Conference on the Use of Radioisotopes in the Physical Sciences and Industry, Copenhagen (Denmark), 6-17 Sep 1960; Other Information: 3 tabs, 4 refs; Related Information: In: Radioisotopes in the Physical Sciences and Industry. Proceedings of the Conference on the Use of Radioisotopes in the Physical Sciences and Industry. V. III| 652 p.
Subject:
07 ISOTOPES AND RADIATION SOURCES; CARBON 14; EXTRACTION; IODIDES; IODINE; IODINE 131; KINETICS; LABELLING; LIQUIDS; PLASTICS; SCINTILLATION COUNTING; TOLUENE
OSTI ID:
22025721
Research Organizations:
International Atomic Energy Agency, Vienna (Austria); United Nations Educational, Scientific and Cultural Organization, Paris (France)
Country of Origin:
IAEA
Language:
English
Other Identifying Numbers:
Other: ISSN 0074-1884; TRN: XA12N1737113014
Submitting Site:
INIS
Size:
page(s) 179-186
Announcement Date:
Jan 16, 2013

Conference:

Citation Formats

Broadbank, R W.C., Harhash, A H.E., and Kanchanalai, S. Some symmetrical halogen and methoxy exchange reactions in aromatic systems; Quelques reactions symetriques d'echanges d'halogenes et de groupes methoxyles dans les composes aromatiques; Simmetricheskie reaktsii s galoidnym i metoksidnym obmenom v aromaticheskikh sistemakh; Algunas reacciones simetricas de intercambio de halogenos y grupos metoxilo en compuestos aromaticos. IAEA: N. p., 1962. Web.
Broadbank, R W.C., Harhash, A H.E., & Kanchanalai, S. Some symmetrical halogen and methoxy exchange reactions in aromatic systems; Quelques reactions symetriques d'echanges d'halogenes et de groupes methoxyles dans les composes aromatiques; Simmetricheskie reaktsii s galoidnym i metoksidnym obmenom v aromaticheskikh sistemakh; Algunas reacciones simetricas de intercambio de halogenos y grupos metoxilo en compuestos aromaticos. IAEA.
Broadbank, R W.C., Harhash, A H.E., and Kanchanalai, S. 1962. "Some symmetrical halogen and methoxy exchange reactions in aromatic systems; Quelques reactions symetriques d'echanges d'halogenes et de groupes methoxyles dans les composes aromatiques; Simmetricheskie reaktsii s galoidnym i metoksidnym obmenom v aromaticheskikh sistemakh; Algunas reacciones simetricas de intercambio de halogenos y grupos metoxilo en compuestos aromaticos." IAEA.
@misc{etde_22025721,
title = {Some symmetrical halogen and methoxy exchange reactions in aromatic systems; Quelques reactions symetriques d'echanges d'halogenes et de groupes methoxyles dans les composes aromatiques; Simmetricheskie reaktsii s galoidnym i metoksidnym obmenom v aromaticheskikh sistemakh; Algunas reacciones simetricas de intercambio de halogenos y grupos metoxilo en compuestos aromaticos}
author = {Broadbank, R W.C., Harhash, A H.E., and Kanchanalai, S}
abstractNote = {Isotope tracers are essential in the study of the kinetics of symmetrical nucleophilic substitution reactions at an aromatic carbon atom. The iodine exchange between iodo-nitro-aromatic compounds and iodide ions in acetone or methanol solution has been studied both qualitatively and quantitatively by labelling the iodide ions with iodine-131. The reaction mixture is sampled at convenient time intervals, the two reactants separated by toluene-water extraction, and the progress of the reaction ascertained by beta-counting with a liquid Geiger counter. Measurements have been extended to 'carrier-free' concentrations of iodide ions. The preparation of certain nitro-methoxy-aromatic compounds, labelled with carbon-14 in the methoxy group, is described. Symmetrical methoxy exchange reactions of these compounds with methoxide ions, in methanol solution, have been studied. After separation of the reactants (from samples of the reaction mixture taken at convenient time intervals) by toluene-water extraction, the aromatic compounds are recovered and then specific activities determined by beta-scintillation counting with a plastic phosphor. In the discussion of the experimental data, special attention is paid to the effect of ionic strength on the specific rate of the reaction. Comparison is made with ionic strength effects observed in symmetrical biomolecular nucleophilic reactions at a saturated (aliphatic) carbon atom, and reference is made to certain other aromatic nucleophilic substitution reactions. (author) [French] Les indicateurs radioactifs sont indispensables pour l'etude cinetique des reactions symetriques de substitution nucleophilique dans l'atome carbone de aromatique. L'echange d'iode entre des composes iodo-nitro-aromatiques et des ions iodure dissous dans de l'acetone ou du methanol a ete etudie a la fois quantitativement et qualitativement par marquage des ions iodure a l'iode-131. Le melange reactif a ete echantillonne a des intervalles appropries, les deux phases separees par extraction a l'aide de toluene et d'eau, et les progres de la reaction controles par un comptage beta fait avec un compteur Geiger pour fiquides. Les mesures ont ete effectuees egalement pour des concentrations d'ions iodure . Les auteurs du memoire decrivent ensuite la preparation de certains composes nitro-methoxy-aromatiques marques au carbone-14 dans le groupe methoxyle, ainsi que les reactions symetriques d'echange de groupes methoxyles entre ces composes et des ions methoxydes dans une solution de methanol. Apres separation des produits en reaction (echantillons du melange reactif preleves a des intervalles appropries) par extraction au moyen de toluene et d'eau, les composes aromatiques sont recuperes et leur activite specifique est determinee par comptage beta avec un scintillateur en matiere plastique. En analysant les donnees obtenues, les auteurs accordent une attention particuliere aux effets de la force ionique sur la vitesse specifique de reaction. Ils les comparent aux effets de la force ionique observes dans les reactions ruicleophiliques bimoleculaires symetriques sur un atome de carbone (aliphatique) sature et se referent a certaines autres reactions de substitution nucleophilique clans les composes aromatiques. (author) [Spanish] Los trazadores isotopicos son indispensables para el estudio de la cinetica de las reacciones simetricas de sustitucion nucleofilica en los atomos de carbono aromaticos. Con ayuda de iones yoduro marcados con yodo-131, los autores estudiaron cualitativa y cuantitativamente el intercambio de yodo entre compuestos yodo-nitroaromaticos e iones yoduro disueltos en acetona o metanol. A intervalos de tiempo apropiados, tomaron muestras de la mezcla, separaron los reactivos por extraccion con tolueno y agua y estucharon el curso de la reaccion por recuento beta en un contador Geiger para liquidos. Extendieron el intervalo de medicion hasta concentraciones de iones yoduro libres de portador. Los autores describen seguidamente la preparacion de ciertos compuestos nitrometoxi- aromaticos marcados con carbono-14 en el grupo metoxilo. Estudiaron reacciones simetricas de intercambio de grupos metoxilo entre estos compuestos e iones metoxilo disueltos en metanol. Despues ele separar los reactivos (en muestras de la meczla tomada a intervalos adecuados) por extraccion con tolueno y agua, recuperaron los compuestos aromaticos y determinaron sus actividades especificas por recuento mediante un fosforo ele plastico. Al analizar los resultados experimentales, dedican particular atencion a la influencia ejercida por la fuerza ionica sobre la velocidad especifica de reaccion. Establecen comparaciones con los efectos ele la fuerza ionica observados en las reacciones simetricas nucleofilicas biomoleculares en un atomo de carbono (alifatico) saturado, y mencionan algunas otras reacciones de sustituciones nucleofilicas en compuestos aromaticos. (author) [Russian] Izotopnye indikatory nezamenimy pri izuchenii kinetiki reaktsij s nukliofil'nosimmetricheskim zameshcheniem pri aromaticheskom atome ugleroda. Obmen joda mezhdu jodo-nitro-aromaticheskimi soedineniyami i ionami jodida v atsetonovom ili metanolovom rastvore izuchalsya kak s kachestvennoj, tak i kolichestvennoj tochek zreniya posredstvom mecheniya ionov jodida jodom-131. U smesi reaktsii pri opredelennykh intervalakh vremeni bralis' obraztsy, dva reaktanta razdelyalis' toluolovodnoj ehkstraktsiej, a khod reaktsii opredelyalsya beta-otschetom zhidkostnogo schetchika Gejgera-Myullera. Izmereniya rasprostranyalis' takzhe na ''svobodnye ot nositelya'' kontsentratsii ionov jodida. Privoditsya opisanie prigotovleniya nekotorykh nitro-metoksi-aromaticheskikh soedinenij, mechennykh uglerodom-14 v metoksinovoj gruppe. Privoditsya issledovanie reaktsij simmetricheskogo metoksinovogo obmena ehtikh soedinenij s metoksidnymi ionami v metanovom rastvore. Posle otdeleniya reaktantov (iz obraztsov smesi reaktsii, vzyatykh cherez udobnye intervaly vremeni) s pomoshch'yu toluolo-vodnoj ehkstraktsii izvlekayutsya aromaticheskie soedineniya, a ikh udel'naya aktivnost' opredelyaetsya beta-stsintillyatsionnym schetom s plastmassovym fosforom. Pri rassmotrenii ehksperimental'nykh dannykh udelyalos' osoboe vnimanie vliyaniyu ionnoj intensivnosti na udel'nuyu skorost' reaktsii. Daetsya sravnenie s vliyaniem ionnoj intensivnosti, nablyudaemoj v simmetricheskikh bimolekulyarnykh nukleofil'nykh reaktsiyakh pri nasyshchennom (alifaticheskom) atome ugleroda; privoditsya ssylka na nekotorye drugie aromaticheskie nukleofil'nye reaktsii zameshcheniya. (author)}
place = {IAEA}
year = {1962}
month = {Mar}
}