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Property of conjugated systems with 4n delocalized electrons
prototypical example of antiaromaticity, cyclobutadiene, is the subject of debate, with some scientists arguing that antiaromaticity is not a major factor
Antiaromaticity
System of connected p-orbitals with delocalized electrons in a molecule
The lack of conjugation allows the 8 π electron molecule to avoid antiaromaticity, a destabilizing effect associated with cyclic, conjugated systems
Conjugated_system
Chemical compound
challenges posed by the inherent strain and antiaromaticity of the azete ring. Due to their antiaromaticity and strain, azetes are extraordinarily reactive
Azete
Chemical compound
COT is an antiaromatic compound as it possesses 8 π electrons. In contrast to the aromaticity commonly seen in benzene rings, antiaromaticity destabilises
Cyclooctatetraene
Russian-American scientist
aluminum clusters, and chemical bonding theory, especially aromaticity / antiaromaticity in all-metal structures, and development of the Adaptive Natural Density
Alexander_Boldyrev
Electric current observed in aromatic compounds
associated with aromaticity whereas a paratropic ring current signals antiaromaticity. A similar effect is observed in three-dimensional fullerenes; in this
Aromatic_ring_current
Computational methods for identifying aromatic ring systems
cyclobutadiene) are antiaromatic and destabilized. Most cheminformatics aromaticity models do not explicitly handle antiaromaticity, though they correctly
Aromaticity_(cheminformatics)
Completely conjugated monocyclic hydrocarbons
[4]annulene). Cyclobutadiene is the only annulene with considerable antiaromaticity, since planarity is unavoidable. With [8]annulene, the molecule takes
Annulene
Chemical compound
studies have been conducted to assess the consequences of antiaromaticity in boroles. Their antiaromatic character entails strong electrophilicity of the boron
Borole
Chemical compound
atoms with p orbitals, maleic anhydride was long thought to exhibit antiaromaticity. However, a thermochemical study concluded that only 8 kJ/mol of destabilization
Maleic_anhydride
Chemical compound
signals in a 2 to 1 ratio. The addition of two electrons removes the antiaromaticity; it becomes a planar 10π-electron aromatic species and is thus a bicyclic
Pentalene
Non-orientable surface with one edge
Seok; Osuka, Atsuhiro; Kim, Dongho (May 2009). "Möbius aromaticity and antiaromaticity in expanded porphyrins". Nature Chemistry. 1 (2): 113–122. Bibcode:2009NatCh
Möbius_strip
Chemical property
containing 4n π electrons are called antiaromatic and are, in general, destabilized. Molecules that could be antiaromatic will tend to alter their electronic
Aromaticity
Chemical compound
Schleyer, Paul (2012). "Is cyclobutadiene really highly destabilized by antiaromaticity?". Chemical Communications. 48 (67): 8437–9. doi:10.1039/c2cc33521b
Cyclobutadiene
Method of determining aromaticity in organic molecules
OCLC 642506595. Ayub, Rabia (2017). "Excited State Aromaticity and Antiaromaticity. Fundamental Studies and Applications" (PDF). Uppsala University. p
Hückel's_rule
Subdiscipline of chemistry, focusing on carbon compounds
delocalized pi electrons, where n is an integer. Particular instability (antiaromaticity) is conferred by the presence of 4n conjugated pi electrons. The characteristics
Organic_chemistry
Class of heterocyclic compounds
4-dithiins. Planar dithiins are 8π e− systems, which would lead to antiaromaticity if the structure was planar. Akin to the behavior of cyclooctatetraene
Dithiin
Chemical compound
cyclopropene, but with the methylene group replaced by sulfur. It is antiaromatic and very labile. No thiirene has been isolated at room temperature, but
Thiirene
Rule in organic chemistry
Kristine; Ottosson, Henrik (2014-05-28). "Excited State Aromaticity and Antiaromaticity: Opportunities for Photophysical and Photochemical Rationalizations"
Baird's_rule
Chemical compound
atom. The parent compound, C6H6S is unstable and is predicted to be antiaromatic. Bulky derivatives have been isolated and shown by X-ray crystallography
Thiepine
Chemical compound
Zhiyuan; Hosmane, Ramachandra S.; Liebman, Joel F. (1997). "The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide
N-Methylmaleimide
Laiter, A Pross (1996 )Thermochemical assessment of the aromatic and antiaromatic characters of the cyclopropenyl cation, cyclopropenyl anion, and cyclopropenyl
Addy_Pross
notes (cyclobutadiene)Fe(CO)3 12078-17-0 orange solid, b.p. 47 °C (3 mm) antiaromatic ligand (butadiene)Fe(CO)3 12078-32-9 yellow-orange, m.p. 19 °C major
(Diene)iron_tricarbonyl
Chemical compound
structure and conformation. 14. Is bicyclo[6.2.0]decapentaene aromatic or antiaromatic?". J. Org. Chem. 50 (15): 2684–2688. doi:10.1021/jo00215a018. Schein
Naphthalene
Chemical theory
of aromatic, suprafacial electron systems; likewise, (4r)a refers to antiaromatic, antarafacial systems. It can be shown that if the total number of these
Frontier molecular orbital theory
Frontier_molecular_orbital_theory
Mechanism of spontaneous symmetry breaking
other areas of chemistry. In organic chemistry, the phenomenon of antiaromaticity has the same cause and also often sees molecules distorting; as in
Jahn–Teller_effect
Chemical compound
being a non-aromatic compound - neither behaving as aromatic nor an antiaromatic one. For this reason, benzocyclobutadiene will readily dimerize or polymerize
Benzocyclobutadiene
Organic ring compounds with the formula C2H3N
analogs of aziridines. Azirine, the parent compound, has two isomers: the antiaromatic 1H-azirine, containing a carbon–carbon double bond, is not stable and
Azirine
Special type of aromaticity
Zin; Osuka, Atsuhiro; Kim, Dongho (2009). "Möbius aromaticity and antiaromaticity in expanded porphyrins". Nature Chemistry. 1 (2): 113–122. doi:10.1038/nchem
Möbius_aromaticity
Set of rules pertaining to pericyclic reactions
Möbius) and electron count (4n + 2 or 4n) results in either an aromatic or antiaromatic transition state. Meanwhile, Kenichi Fukui analyzed the frontier orbitals
Woodward–Hoffmann_rules
Organic chemical reaction
anionic transition state on the other hand 4 electrons are present thus antiaromatic and destabilized. A radical transition state is neither stabilized or
1,2-rearrangement
Chemical compound
first π-electronic hydrocarbon systems discovered to show evidence of antiaromaticity. The spectral and chemical properties show the influence of the central
Biphenylene
Model to predict the geometry of molecules
repulsion (VSEPR), softness-hardness-based models, aromaticity and antiaromaticity, hyperconjugation, etc. The application to main-group element compounds
Second-order Jahn-Teller distortion in main-group element compounds
Second-order_Jahn-Teller_distortion_in_main-group_element_compounds
American physical chemist
molecules. After the completion of his Ph.D., Wasielewski studied antiaromaticity under the direction of Ronald Breslow at Columbia University. Wasielewski
Michael_R._Wasielewski
Allotrope of boron
"Hydrocarbon analogues of boron clusters — planarity, aromaticity and antiaromaticity". Nature Materials. 2 (12): 827–833. Bibcode:2003NatMa...2..827Z. doi:10
Borophene
Reaction with a cyclic transition state
(4n + 2)-electron Möbius and 4n-electron Hückel transition states are antiaromatic and are thus strongly disfavored. Aromatic transition state theory results
Pericyclic_reaction
Japanese chemist
Seok; Osuka, Atsuhiro; Kim, Dongho (May 2009). "Möbius aromaticity and antiaromaticity in expanded porphyrins". Nature Chemistry. 1 (2): 113–22. Bibcode:2009NatCh
Atsuhiro_Osuka
Chemical reaction in which a ring is formed/broken by adding/removing a single atom
direction. Using Hückel's rule, one can tell if the π-system is aromatic or antiaromatic. If aromatic, linear approaches use disrotatory motion while non-linear
Cheletropic_reaction
Chemical compound
the component cyclobutadiene and cyclooctatetraene component rings are antiaromatic, but when fused together the rings counteract each other. Bicyclo[6.2
Bicyclo(6.2.0)decapentaene
Chemical reaction
product, or can undergo a 4π electrocyclic ring closure, to form an antiaromatic oxirene. This oxirene can reopen in two ways, to either α-ketocarbene
Wolff_rearrangement
Class of prism-shaped hydrocarbons
stable. The prismanes have also been studied in terms of the aromatic or antiaromatic nature of the cage. Hexaprismane in particular would not be thermodynamically
Prismanes
Law of photochemistry
explanation was proposed which pointed out that the S1 excited state has antiaromatic character while the S2 excited state is aromatic. A corollary of Kasha's
Kasha's_rule
Cyclic nitrogen compound with formula HN5
The cyclic pentazolium cation (N+ 5) is not known due to its probable antiaromatic character; whereas the open-chained pentazenium cation (N+ 5) is known
Pentazole
Aromatic organic compounds consisting only of a conjugated planar ring system
integer starting at zero. In contrast, molecules with 4n pi electrons are antiaromatic. Aromatic compound Polycyclic aromatic hydrocarbon (PAH) Clayden, J.;
Simple_aromatic_ring
cyclohexabenzocoronenylenes. Moreover, several nanohoops containing such antiaromatic units as dibenzo[a,e]pentalene and pyrrolo[3,2-b]pyrrole are reported
Carbon_nanohoop
English typographer (born 1940)
at The Poster Archive – Basel, Switzerland 2024: Chemistry World – Antiaromaticity – Typographic artwork for magazine 2024: Johns Hopkins Magazine – Breaking
Alan Kitching (typographic artist)
Alan_Kitching_(typographic_artist)
Chemical compound
techniques found the configuration to be extremely strained and proposed an antiaromatic 4π electron system, as such oxirene is expected to be very high energy
Oxirene
Organic compounds with a saturated carbon-carbon-sulfur ring
derived by the formal addition of sulfur atom to an alkyne. They are antiaromatic and rarely observed. S-Alkylthiirenium salts are, however, known. Wataru
Episulfide
Chemical compound
Cyclododecahexaene or [12]annulene (C 12H 12) is a member of the series of annulenes with some interest in organic chemistry with regard to the study of
Cyclododecahexaene
American chemist
Evans) to understanding pericyclic reactivity based on aromatic and antiaromatic transition states. He did not however believe in the utility of Möbius
Michael_J._S._Dewar
Class of chemical compounds
9-borafluorenes are generally less reactive than boroles due to less antiaromatic character and Lewis acidity. Containing highly conjugated π systems,
9-Borafluorene
Russian chemist
с. Minkin V. I., Glukhovtsev M. N., Simkin B. Ya. Aromaticity and Antiaromaticity: Electronic and Structural Aspects. — New York: Wiley Intersci., 1994
Vladimir_Minkin
Molecule which completely entraps another within itself
reactivity was observed. He used a hemicarcerand to isolate highly unstable, antiaromatic cyclobutadiene at room temperature. The hemicarcerand stabilizes guests
Carcerand
Class of ions
elucidated by Eggers Doering and Knox in 1954. On the other hand, the antiaromatic cyclopentadienyl cation (C5H+5) is destabilized by some 40 kcal/mol.
Carbenium_ion
Class of chemical compounds
unsymmetrically disubstituted formally antiaromatic [2,1-a]IF derivative was reported by the Das group that displays strong antiaromaticity of the ortho-quinoidal as-indacene
Indenofluorene
Chemical compound
contrast, the corresponding [12]- and [16]annulenes, which are weakly antiaromatic or nonaromatic, have downfield shifted interior hydrogens. However, unlike
Cyclotetradecaheptaene
German-American scientist (born 1967)
Irle, Stephan; Kim, Dongho; Shinokubo, Hiroshi (2016-11-30). "Stacked antiaromatic porphyrins". Nature Communications. 7 (1) 13620. doi:10.1038/ncomms13620
Stephan_Irle
Chemical compound
Journey from Benzoborirene to Benzoborole-Supported 1,2-Diimine and Antiaromatic Borolediide". Angewandte Chemie International Edition. 62 (51) e202312608
Borirene
Chemical compound
1,2-Dioxin is a heterocyclic, organic, antiaromatic compound with the chemical formula C4H4O2. It is an isomeric form of 1,4-dioxin (or p-dioxin). Due
1,2-Dioxin
Chemical compound
around one or the other four-membered ring alone would be a less-stable antiaromatic form, as is seen in cyclobutadiene itself. Propalene Pentalene Heptalene
Butalene
Theory in computational chemistry
Paul von Ragué (2006-02-20). "An Energetic Measure of Aromaticity and Antiaromaticity Based on the Pauling–Wheland Resonance Energies". Chemistry - A European
Natural_resonance_theory
Organic Chemistry researcher
1997 to 1999, where she worked on dinuclear metalloenzyme mimics and antiaromaticity. Waters joined UNC-Chapel Hill as an assistant professor in 1999. As
Marcey_Waters
Organic molecular structure
compounds. Just as aromatic compounds exhibit exceptional stability, antiaromatic compounds, which deviate from Huckel's rule and contain a closed loop
Homoaromaticity
Instrument used to physically scan the surface of a sample
Carlos-Andres; Müllen, Klaus (2017). "Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine
Probe_tip
Chemical compound
metals, electrochemically and with bases. The corannulene dianion is antiaromatic and tetraanion is again aromatic. With lithium as reducing agent two
Corannulene
Class of chemical compounds
"Silicon-containing formal 4π-electron four-membered ring systems: antiaromatic, aromatic, or nonaromatic?". Chemistry: A European Journal. 18 (24):
Cyclodiphosphazane
French chemist
Taquet, M.-M. Rohmer, M. Bénard, R. Welter « A 6π + 6π potentially antiaromatic zwitterion preferred to a quinoidal structure: Its reactivity towards
Pierre_Braunstein
Chemical compound
some scientific interest as a stable derivative of the highly reactive antiaromatic pentalene by benzannulation. The first derivative was synthesised in
Dibenzopentalene
Chemical compound
Acepentalene is a tricyclic anti-aromatic compound. Its molecular formula is C10H6. It consists of three five-membered rings fused across three of the
Acepentalene
British chemist (1927–2006)
chemistry of new heterocyclic rings, with an emphasis on aromatic and antiaromatic rings, and the role of reactive intermediates in heterocyclic chemistry
Charles_Rees
Chemical compound
cyclopentadienyl anions (six π electrons each). cis-Bicalicene, by contrast, is an antiaromatic hydrocarbon. A resonance structure with four aromatic rings, analogous
Bicalicene
Organophosphorus compound
Although the 4πn conjugated system would suggest that the molecule exhibits antiaromatic character, geometric and magnetic criteria confirm that the complex is
Phosphorus_porphyrin
Series of chemical compounds
orbital of the PY+ 2 fragment and π orbitals also leads to some degree of antiaromatic character. Therefore, net 3-center conjugative effect is a combination
Phosphirenium_ion
ANTIAROMATICITY
ANTIAROMATICITY
ANTIAROMATICITY
ANTIAROMATICITY
Boy/Male
Hindu, Indian, Malayalam, Marathi
Lord Rama; King of Kaushal
Girl/Female
Muslim
Quiet, Serious
Boy/Male
Norse
Brother of Gudrun.
Female
Croatian
, bitter.
Male
Norse
Norse name NÃÃHÖGGR means "dreaded striker." In mythology, this is the name of a dragon or serpent who gnaws at the roots of the world tree Yggdrasill.
Girl/Female
Hindu, Indian, Kannada, Sanskrit, Tamil
Calm
Girl/Female
English
Derived from Victoria: triumphant.
Boy/Male
Tamil
Inside viewer, Wink
Girl/Female
Gujarati, Hindu, Indian, Marathi, Sanskrit
World; Universe; Earth
Boy/Male
Polish American Latin Slavic
Flowering.
ANTIAROMATICITY
ANTIAROMATICITY
ANTIAROMATICITY
ANTIAROMATICITY
ANTIAROMATICITY