Atranes are a class of tricyclic molecules with three five-membered rings. It is a heterocyclic structure similar to the propellanes. It has a transannulardative bond from a nitrogen at one bridgehead to a Lewis acidic atom such as silicon or boron at the other bridgehead.[1] The name "atrane" was first proposed by Mikhail Grigorievich Voronkov [ru].[1]
Various atranes are named depending on the central element, e.g. "silatrane" (E = silicon); "boratrane" (E = boron); "phosphatrane" (E = phosphorus), etc. It is also proposed that when Y = nitrogen, the prefix "aza" be inserted before element + "atrane" (azasilatrane, for example) because atranes wherein E = silicon and Y = oxygen have been referred to as just "silatranes".[2]
Structure and propertiesedit
From left to right: atrane, quasiatrane and proatrane
Silatranes exhibit unusual properties as well as biological activity in which the coordination of nitrogen to silane plays an important role. Some derivatives such as phenylsilatrane are highly toxic.
The transannular coordinate bond in atranes can be stretched (quasiatranes) and even broken (proatranes,) by controlling their stereoelectronic properties. The strength of the transannular interaction depends on the electronegativity of the participating atoms and the size of the rings.
^ abVoronkov, Mikhail G.; Baryshok, Viktor P. "Atranes - a new generation of biologically active substances" (in Russian) Vestnik Rossiiskoi Akademii Nauk 2010, volume 80, 985-992.
^Verkade, John G. (1994). "Main group atranes: Chemical and structural features". Coordination Chemistry Reviews. 137: 233–295. doi:10.1016/0010-8545(94)03007-D.
^Verkade, John G.; Urgaonkar, Sameer; Verkade, John G.; Urgaonkar, Sameer (2012). "Proazaphosphatrane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00702.pub2. ISBN978-0471936237.
^Chalkley, Matthew J.; Drover, Marcus W.; Peters, Jonas C. (2020). "Catalytic N2-to-NH3 (or -N2H4) Conversion by Well-Defined Molecular Coordination Complexes". Chemical Reviews. 120 (12): 5582–5636. doi:10.1021/acs.chemrev.9b00638. PMC7493999. PMID 32352271.
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April 13, 2024
atrane, class, tricyclic, molecules, with, three, five, membered, rings, heterocyclic, structure, similar, propellanes, transannular, dative, bond, from, nitrogen, bridgehead, lewis, acidic, atom, such, silicon, boron, other, bridgehead, name, atrane, first, p. Atranes are a class of tricyclic molecules with three five membered rings It is a heterocyclic structure similar to the propellanes It has a transannular dative bond from a nitrogen at one bridgehead to a Lewis acidic atom such as silicon or boron at the other bridgehead 1 The name atrane was first proposed by Mikhail Grigorievich Voronkov ru 1 Contents 1 Nomenclature 2 Structure and properties 3 See also 4 ReferencesNomenclature edit nbsp Ball and stick model of the allyl silatrane moleculeVarious atranes are named depending on the central element e g silatrane E silicon boratrane E boron phosphatrane E phosphorus etc It is also proposed that when Y nitrogen the prefix aza be inserted before element atrane azasilatrane for example because atranes wherein E silicon and Y oxygen have been referred to as just silatranes 2 Structure and properties edit nbsp From left to right atrane quasiatrane and proatraneSilatranes exhibit unusual properties as well as biological activity in which the coordination of nitrogen to silane plays an important role Some derivatives such as phenylsilatrane are highly toxic The transannular coordinate bond in atranes can be stretched quasiatranes and even broken proatranes by controlling their stereoelectronic properties The strength of the transannular interaction depends on the electronegativity of the participating atoms and the size of the rings nbsp Protonation of Verkade base gives an atrane 3 Proazaphosphatrane is a very strong non ionic base and is utilized in various types of organic synthesis as an efficient catalyst nbsp Fe 0 N2 complex based on atrane framework 4 See also editStannatrane Hypervalent moleculeReferences edit a b Voronkov Mikhail G Baryshok Viktor P Atranes a new generation of biologically active substances in Russian Vestnik Rossiiskoi Akademii Nauk 2010 volume 80 985 992 Verkade John G 1994 Main group atranes Chemical and structural features Coordination Chemistry Reviews 137 233 295 doi 10 1016 0010 8545 94 03007 D Verkade John G Urgaonkar Sameer Verkade John G Urgaonkar Sameer 2012 Proazaphosphatrane Encyclopedia of Reagents for Organic Synthesis doi 10 1002 047084289X rn00702 pub2 ISBN 978 0471936237 Chalkley Matthew J Drover Marcus W Peters Jonas C 2020 Catalytic N2 to NH3 or N2H4 Conversion by Well Defined Molecular Coordination Complexes Chemical Reviews 120 12 5582 5636 doi 10 1021 acs chemrev 9b00638 PMC 7493999 PMID 32352271 nbsp Wikimedia Commons has media related to atranes Retrieved from https en wikipedia org w index php title Atrane amp oldid 1085711568, wikipedia, wiki, book, books, library,
