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Concept
Cyclopropane
Résumé
Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane itself is mainly of theoretical interest but many of its derivatives are of commercial or biological significance.
Despite its explosive nature, cyclopropane was used as a clinical anesthetic from the 1930s through the 1980s. It is an important precursor in the biosynthesis of plant hormones, and in the chemical synthesis of insecticides.
Cyclopropane was discovered in 1881 by August Freund, who also proposed the correct structure for the substance in his first paper. Freund treated 1,3-dibromopropane with sodium, causing an intramolecular Wurtz reaction leading directly to cyclopropane. The yield of the reaction was improved by Gustavson in 1887 with the use of zinc instead of sodium. Cyclopropane had no commercial application until Henderson and Lucas discovered its anaesthetic properties in 1929; industrial production had begun by 1936. In modern anaesthetic practice, it has been superseded by other agents.
Cyclopropane was introduced into clinical use by the American anaesthetist Ralph Waters who used a closed system with carbon dioxide absorption to conserve this then-costly agent.
Cyclopropane is a relatively potent, non-irritating and sweet smelling agent with a minimum alveolar concentration of 17.5% and a blood/gas partition coefficient of 0.55. This meant induction of anaesthesia by inhalation of cyclopropane and oxygen was rapid and not unpleasant. However at the conclusion of prolonged anaesthesia patients could suffer a sudden decrease in blood pressure, potentially leading to cardiac dysrhythmia: a reaction known as "cyclopropane shock". For this reason, as well as its high cost and its explosive nature, it was latterly used only for the induction of anaesthesia, and has not been available for clinical use since the mid 1980s.
Cylinders and flow meters were coloured orange.
Source officielle
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Proximité ontologique
Concepts associés (8)
Tension de cycle
En chimie organique, la tension de cycle ou contrainte cyclique désigne la déstabilisation d'une molécule cyclique, telle un cycloalcane, causée par l'orientation spatiale des atomes qui la composent. Cette tension provient d'une combinaison (1) de contrainte d'angle, (2) de contrainte de torsion (ou tension de Pitzer) et (3) de la tension trans-annulaire (ou contrainte de van der Waals).
Strain (chemistry)
In chemistry, a molecule experiences strain when its chemical structure undergoes some stress which raises its internal energy in comparison to a strain-free reference compound. The internal energy of a molecule consists of all the energy stored within it. A strained molecule has an additional amount of internal energy which an unstrained molecule does not. This extra internal energy, or strain energy, can be likened to a compressed spring.
Cycloalcane
En chimie organique, les cycloalcanes (ou cyclanes) sont une série de molécules contenant deux atomes d'hydrogène par carbone et arrangées en forme d'anneau. Ils font partie des composés alicycliques. La formule générale de ce type de composé est : CH. Les trois principaux éléments de la série : Fichier:Cycloalcanes.svg La méthode de nommage de l'UICPA pour ce type de composé est très simple. Lorsque l'alcane cyclique constitue la chaîne principale, il suffit de prendre le nom de l'alcane correspondant et de le faire précéder de cyclo .