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Molecule containing main group elements with more than eight valence electrons
In chemistry, a hypervalent molecule (the phenomenon is sometimes colloquially known as expanded octet) is a molecule that contains one or more main group
Hypervalent_molecule
Mixing (superposition) of atomic orbitals
definitively excluding the role of d-orbital hybridisation in bonding in hypervalent compounds of second-row (period 3) elements, ending a point of contention
Orbital_hybridisation
Model of chemical bonding in which three atoms share four electrons
4-electron (3c–4e) bond is a model used to explain bonding in certain hypervalent molecules such as tetratomic and hexatomic interhalogen compounds, sulfur
Three-center four-electron bond
Three-center_four-electron_bond
Chemical rule of thumb
that hypervalent molecules violate the octet rule, ab initio calculations show that almost all known examples obey the octet rule. The molecules form
Octet_rule
Chemical compound and greenhouse gas
of six fluorine atoms attached to a central sulfur atom. It is a hypervalent molecule.[citation needed] Typical for a nonpolar gas, SF 6 is poorly soluble
Sulfur_hexafluoride
Chemical compound
violently with water to produce highly corrosive sulfuric acid. Hypervalent molecule Sulfur trioxide pyridine complex Greenwood, Norman N.; Earnshaw,
Sulfur_trioxide
Ion
iodine-atom. In the molecular orbital model, a common explanation for the hypervalent bonding on the central iodine involves a three-center four-electron bond
Triiodide
Chemical compound of sulfur and oxygen
known to medieval alchemists as "volatile spirit of sulfur". SO2 is a bent molecule with C2v symmetry point group. A valence bond theory approach considering
Sulfur_dioxide
Chemical compound
solid. A molecule of pentaphenylbismuth consists of five phenyl groups attached to one bismuth atom. In this compound, bismuth is hypervalent. Pentaphenylbismuth
Pentaphenylbismuth
Organic derivative of iodine
many λ5‑iodanes are dodecet molecules, and hypothetical λ7‑iodanes are tetradecet molecules. As with other hypervalent compounds, N‑X‑L notation can
Hypervalent organoiodine compounds
Hypervalent_organoiodine_compounds
Description of a molecule's true bond structure as a combination of structures
participation of d orbitals is unimportant, and the bonding of so-called hypervalent molecules are, for the most part, better explained by charge-separated contributing
Resonance_(chemistry)
Chemical compound
fluorine atoms as Shyp (for hypervalent) and Stop. The fluorine atoms are labelled Ftop attached to Stop, and on the hypervalent S atom: Fcis, the closest
Difluorodisulfanedifluoride
Chemical compound
solid that easily undergoes sublimation. The compound is an example of a hypervalent sulfur compound called a sulfurane. As such, the sulfur adopts a see-saw
Martin's_sulfurane
Any chemical compound having at least one fluorine atom
in the periodic table.) Lower-period elements, however, may form hypervalent molecules, such as phosphorus pentafluoride or sulfur hexafluoride. The reactivity
Fluorine_compounds
Chemical compound
3 pm and S–Feq = 154.2 pm. It is typical for the axial ligands in hypervalent molecules to be bonded less strongly. The 19F NMR spectrum of SF4 reveals
Sulfur_tetrafluoride
Combining capacity of elements with other atoms
electronegativity of the two bonded atoms. Pauling also considered hypervalent molecules, in which main-group elements have apparent valences greater than
Valence_(chemistry)
Chemical compound
noncoordinating anions. In contrast to this tetrachloride, SF4 is a neutral molecule. It decomposes above −30 °C (242 K) to sulfur dichloride and chlorine.
Sulfur_tetrachloride
used by many force fields, and allows the VALBOND method to handle hypervalent molecules and transition metal complexes. The VALBOND energy term has been
VALBOND
Chemical compound
Tetraethylammonium trichloride (also known as Mioskowski reagent) is a chemical compound with the formula [(CH3CH2)4N][Cl3] consisting of a tetraethylammonium
Tetraethylammonium trichloride
Tetraethylammonium_trichloride
Chemical compound
Gaseous and molten PCl5 is a neutral molecule with trigonal bipyramidal geometry and (D3h) symmetry. The hypervalent nature of this species (as well as
Phosphorus_pentachloride
Field of chemistry
than predicted by the octet rule, as explained in the article on hypervalent molecules. The mechanisms of their reactions differ from organic compounds
Inorganic_chemistry
Chemical element with atomic number 9 (F)
Noury, S.; Silvi, B.; Gillespie, R. J. (2002). "Chemical Bonding in Hypervalent Molecules: Is the Octet Rule Relevant?" (PDF). Inorganic Chemistry. 41 (8):
Fluorine
German chemist, winner of the 1953 Nobel Prize in Chemistry (1881–1965)
fundamental contributions in polymer science. Beta-lactam Carbene Hypervalent molecule Polyoxymethylene Pyrethrin Triphenylphosphine phenylimide Heidegger
Hermann_Staudinger
Chemical compound
bipyramidal structure, with D5h symmetry, as predicted by VSEPR theory. The molecule can undergo a pseudorotational rearrangement called the Bartell mechanism
Iodine_heptafluoride
Diagrams for the bonding between atoms of a molecule and lone pairs of electrons
also be moved in the same way to create resonance structures for hypervalent molecules such as sulfur hexafluoride, which is the correct description according
Lewis_structure
Class of hypervalent organoiodine compounds
An iminoiodinane (also known as iminoiodane or iodonium imide) is a hypervalent organoiodine compound with the general formula R-IN-R', where R and R'
Iminoiodinane
Chemical compound
bound to a bismuth atom with formula Bi(CH3)5. It is an example of a hypervalent compound. The molecular shape is trigonal bipyramid. Pentamethylbismuth
Pentamethylbismuth
Shape of certain five-ligand chemical complexes
of acetylacetone (2,4-pentanedione)). AXE method Square pyramid Hypervalent molecule Molecular geometry Spiro, Thomas G.; Terzis, Aristides; Raymond,
Square pyramidal molecular geometry
Square_pyramidal_molecular_geometry
Chemical compound
materials (wood, paper, oil, clothing, etc.). Chlorine trifluoride Hypervalent molecule https://pubchem.ncbi.nlm.nih.gov/compound/0061654 Greenwood, Norman
Chlorine_pentafluoride
Chemical compound
of several studies, and a definite ground state remains uncertain. The molecule adopts a roughly square pyramidal shape in the unsolvated crystal. In crystals
Pentaphenylantimony
Chemical compound
bound to an antimony atom with formula Sb(CH3)5. It is an example of a hypervalent compound. The molecular shape is trigonal bipyramidal. Some other antimony(V)
Pentamethylantimony
Scientific theory
the phosphorus atom. Thus, the molecule is assumed to expand its bonding beyond the octet, a situation known as hypervalent bonding. LDQ theory, however
Linnett_double-quartet_theory
German chemist (1897–1987)
rearrangement 2,3-Wittig rearrangement Directed ortho metalation Ate complex Hypervalent molecule Potassium tetraphenylborate Awards Otto Hahn Prize for Chemistry
Georg_Wittig
Chemical compound
bound to an arsenic atom with formula As(CH3)5. It is an example of a hypervalent compound. The molecular shape is trigonal bipyramid. The first claim
Pentamethylarsenic
Chemical compound with hydrogen and chalcogen atoms
Markku R. (1999). "Chemical Bonding in Hypervalent Molecules Revised. 2. Application of the Atoms in Molecules Theory to Y2XZ and Y2XZ2 (Y = H, F, CH3;
Hydrogen_chalcogenide
Chemical compound
C6H5I(O2CCH3)2 + KI + H2SO4 + KHSO4 The PIDA molecule is termed hypervalent as its iodine atom (technically a hypervalent iodine) is in its +3 oxidation state
(Diacetoxyiodo)benzene
Chemical compound
SeCl4 has often been used as an example for teaching VSEPR rules of hypervalent molecules. As such, one would predict four bonds but five electron groups
Selenium_tetrachloride
Empirical observation in organic chemistry
with 120° angles and sp2 hybridization. It generally does not apply to hypervalent heteroatoms, although they are commonly written with a formal double
Bredt's_rule
Concept on molecular modeling
on valence bond theory and works for large angular distortions, hypervalent molecules, and transition metal complexes. It can be incorporated into other
Force_field_(chemistry)
System of connected p-orbitals with delocalized electrons in a molecule
p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases stability. It is conventionally
Conjugated_system
Chemical compound
the molecule in question would be that of iodine(I), not iodine(III). Eisenberger, P.; Gischig, S.; Togni, A. (2006). "Novel 10-I-3 Hypervalent Iodine-Based
Trifluoromethylation
Organic molecule containing a neutral carbon with two unbound valence electrons
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula
Carbene
Chemical group (–CH2–CH3)
two-carbon moiety in a molecule, while the prefix "eth-" is used to indicate the presence of two carbon atoms in the molecule. Ethylation is the formation
Ethyl_group
Reed, Alan E.; Schleyer, Paul v. R. (1990). "Chemical bonding in hypervalent molecules. The dominance of ionic bonding and negative hyperconjugation over
Covalent_radius_of_fluorine
Class of chemical compounds
in various types of organic synthesis as an efficient catalyst. Hypervalent molecule Scorpionate ligand Chinese lantern structure Voronkov, Mikhail G
Atrane
Chemical compound
Antonio (2008-04-30). "Recent Advances in Electrophilic CF3-Transfer Using Hypervalent Iodine(III) Reagents". CHIMIA International Journal for Chemistry. 62
Togni_reagent_II
Electron-deficient chemical bond where three atoms share two electrons
electronic structure of diborane and the three-centre four-electron bonds of hypervalent sulphur". Journal of Molecular Structure. 186: 43–52. doi:10.1016/0166-1280(89)87037-X
Three-center two-electron bond
Three-center_two-electron_bond
Formalism used for classifying compounds
they have too few electrons as compared to their respective rules, or "hypervalent" when they have too many electrons. Since these compounds tend to be
Electron_counting
American chemist
Martin's sulfurane, illustrating J.C. Martin's interests in hypervalent molecules.
James_Cullen_Martin
Organic compound with a –C≡N functional group
If the nitrile function is not the principal functional group in the molecule, the prefix cyano- is used together with the appropriate locant. In this
Nitrile
Austrian-born American (born 1948)
degradation of Sulfur hexafluoride (SF6) in high-voltage systems. SF6, a hypervalent molecule, is used as a gaseous insulator in conjunction with solid insulating
Isidor_Sauers
equatorial bonds. Hypervalent bonding is described by inclusion of non-bonding MOs, as also invoked for the closely related molecule phosphorus pentafluoride
Phosphoranes
Chemical compounds with the structure R–O–O–R'
Peroxides are a group of molecules with the structure R−O−O−R, where each R represents a radical (a portion of a complete molecule; not a free radical) and
Peroxide
Chemical group (–CH2–)
any part of a molecule that consists of two hydrogen atoms bound to a carbon atom, which is connected to the remainder of the molecule by two single bonds
Methylene_group
Chemical reaction
procedure for the preparation of highly sterically hindered alkenes using a hypervalent iodine reagent" (PDF). Organic & Biomolecular Chemistry. 3 (1): 28–30
Barton–Kellogg_reaction
Chemical group (–CH3) derived from methane
stable group in most molecules. While the methyl group is usually part of a larger molecule, bonded to the rest of the molecule by a single covalent bond
Methyl_group
Technique to describe progression of organic chemistry reaction mechanisms
chemistry of s- and p-block elements. It has been shown to work well for hypervalent compounds. The representation of reaction mechanisms using curved arrows
Arrow_pushing
Organic compound with the structure >C(O–)2
"mixed acetal"). An acetal is formed from and convertible to two alcohol molecules and an aldehyde or ketone, but acetals have substantially different chemical
Acetal
Chemical element with atomic number 6 (C)
and Structures of Hypervalent Pentacoordinate Carbon and Boron Compounds Bearing an Anthracene Skeleton − Elucidation of Hypervalent Interaction Based
Carbon
Organic molecule with two different functional groups
bifunctionality or difunctionality is the presence of two functional groups in a molecule. A bifunctional species has the properties of each of the two types of
Bifunctionality
Group of atoms giving a molecule characteristic properties
chemistry, a functional group is any substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group
Functional_group
Any organic compound containing a C=C=C group
carbon atom, inclined at 45° to the CH2 planes at either end of the molecule. The molecule can thus be thought of as a two-bladed propeller. A third twofold
Allene
Chemical compound
name is also used for the pentyl radical, a pentyl group as an isolated molecule. This free radical is only observed in extreme conditions. Its formula
Pentyl_group
American chemist
and low-coordinate hypervalent sulfur compounds. Thiocarbonyl ylide from Arduengo's Ph.D. dissertation. external viewer. Hypervalent sulfuranide from Arduengo's
Anthony_J._Arduengo
Chemical group (–CH=CH2)
group with the formula −CH=CH2. It is the ethylene (IUPAC name: ethene) molecule (H2C=CH2) with one fewer hydrogen atom. The name is also used for any compound
Vinyl_group
Organic compound
derived from living organisms. The structure of the molecule of urea is O=C(−NH2)2. The urea molecule is planar when in a solid crystal because of sp2 hybridization
Urea
Organic compound containing the functional group R–CH=O
systems achieve aldehydes under chromium-free conditions. One such are the hypervalent organoiodine compounds (i.e., IBX acid, Dess–Martin periodinane), although
Aldehyde
Class of chemical compounds
Arduengo, Anthony J.; Stewart, Constantine A. (1994-07-01). "Low coordinate hypervalent phosphorus". Chemical Reviews. 94 (5): 1215–1237. doi:10.1021/cr00029a003
Nontrigonal pnictogen compounds
Nontrigonal_pnictogen_compounds
Chemical group (=CH–)
(connected to the rest of the molecule by a triple bond) or to the methylidyne radical ⫶CH (the two atoms as a free molecule with dangling bonds). The name
Methine_group
Chemical group derived from alkanes (one hydrogen removed)
the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified)
Alkyl_group
Organic compounds with the structure O=P(OR)3
been a matter of prolonged debate; the phosphorus atom is classically hypervalent, as it possesses more bonds than the octet rule should allow. The focus
Organophosphate
Chemical compound
compound PBr5 is well characterized. AsBr3 is the parent for a series of hypervalent anionic bromoarsenates including [As2Br8]2−, [As2Br9]3−, and [As3Br12]3−
Arsenic_tribromide
Any part of a molecule with the chemical formula –CH2–
part of a molecule with formula −CH2−. The carbon atom is connected by single bonds to two other distinct atoms in the rest of the molecule. A methylene
Methylene_bridge
Nitrogen-based molecule
a synonym for the nitrene class. In the simplest case, the linear N–H molecule (imidogen) has its nitrogen atom sp hybridized, with two of its four non-bonded
Nitrene
Hydrocarbon compound (H2C=CH2)
angle is 117.4°, close to the 120° for ideal sp² hybridized carbon. The molecule is also relatively weak: rotation about the C-C bond is a very low energy
Ethylene
Organophosphorus compound
phosphorus porphyrin. Substituents on the hypervalent phosphorus also result in the existence of a diverse array of molecules with varying properties. Axial substituents
Phosphorus_porphyrin
Type of saturated hydrocarbon compound
(CH4), where n = 1 (sometimes called the parent molecule), to arbitrarily large and complex molecules, like hexacontane (C60H122) or 4-methyl-5-(1-methylethyl)
Alkane
Compound derived from an acid
by ester moieties. Esters of phosphoric acid form the backbone of DNA molecules. Esters of nitric acid, such as nitroglycerin, are known for their explosive
Ester
Hungarian theoretical chemist (born 1955)
observable-based interpretation of electronic wavefunctions: application to “hypervalent” molecules", Computational and Theoretical Chemistry 255, 9 (1992); doi:10
Péter_Surján
Hydrocarbon compound (C6H6)
organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with
Benzene
Chemical group (–OH)
intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds
Hydroxy_group
Organic compound containing C–PO(OR)2 groups
important compounds are phosphonates, including glyphosate (the active molecule of the herbicide Roundup), and ethephon, a widely used plant growth regulator
Phosphonate
Group of chemical compounds derived from alkanes containing one or more halogens
alkane, then replaced by a halogen atom by reaction with a diatomic halogen molecule. Free radical halogenation typically produces a mixture of compounds mono-
Haloalkane
Heterocyclic aromatic organic compound
the number of molecules per cell is only 4. This difference is partly related to the lower symmetry of the individual pyridine molecule (C2v vs D6h for
Pyridine
Halogen compounds derived from methane
protective ozone layer. Like methane itself, halomethanes are tetrahedral molecules. The halogen atoms differ greatly in size and charge from hydrogen and
Halomethane
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
CH3–CH2–O–CH3 is methoxyethane. If the ether is part of a more-complex molecule, it is described as an alkoxy substituent, so –OCH3 would be considered
Ether
Herb known as sweet wormwood
involves cleavage of endoperoxide bridges by iron, producing free radicals (hypervalent iron-oxo species, epoxides, aldehydes, and dicarbonyl compounds) which
Artemisia_annua
Class of chemical substance
metal–organic frameworks for the catalytic oxidation of hydroquinones using hypervalent iodine". Catalysis Science & Technology. 8 (17): 4349–4357. doi:10.1039/C8CY00794B
Metal–organic_framework
Chemical compound
peroxide or peroxymethane) is an organic compound with formula CH 2O 2. The molecule consists of a ring with one methylene and two oxygen atoms. It is of interest
Dioxirane
Chemical compound
carcinogenic metabolite of acrylonitrile and acrylamide. It is a chiral molecule. Glycidamide is a reactive epoxide metabolite from acrylamide and can react
Glycidamide
Chemical compound
metal–organic frameworks for the catalytic oxidation of hydroquinones using hypervalent iodine". Catalysis Science & Technology. 8 (17): 4349–4357. doi:10.1039/C8CY00794B
MIL-53
Functional group (C=O)
the absorption is well understood with respect to the geometry of the molecule. This absorption is known as the "carbonyl stretch" when displayed on an
Carbonyl_group
Chemical element with atomic number 50 (Sn)
square (Sn2−)n sheets), see Papoian, Garegin A.; Hoffmann, Roald (2000). "Hypervalent Bonding in One, Two, and Three Dimensions: Extending the Zintl–Klemm
Tin
Polyatomic ion (NO3, charge –1) found in explosives and fertilisers
accentuating its red coloration. NO is an important biological signaling molecule and intervenes in the vasodilation process. Still, it can also produce
Nitrate
Functional group
the structural formula R−O−CH2−O−R′ which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy group consists of two oxygen
Methylenedioxy
Class of chemical compounds
Risto S.; Pakkanen, Tapani A.; Steudel, Ralf (1987). "Ab initio study of hypervalent sulfur hydrides as model intermediates in the interconversion reactions
Polysulfane
Organic compounds with a carbon-carbon-oxygen ring
According to a reaction mechanism suggested in 1974 at least one ethylene molecule is totally oxidized for every six that are converted to ethylene oxide:
Epoxide
Functional group with the chemical structure R–S–S–R′
their scission, as the S−S bond is usually the weakest bond in an organic molecule.[citation needed] Many specialized organic reactions have been developed
Disulfide
Type of carbene demonstrating particular stability
A persistent carbene (also known as stable carbene) is an organic molecule whose natural resonance structure has a carbon atom with incomplete octet (a
Persistent_carbene
Group 15 elements of the periodic table with valency 5
[clarification needed] Pnictogen compounds with coordination number 5 are hypervalent. Nitrogen(V) fluoride is only theoretical and has not been synthesized
Pnictogen
HYPERVALENT MOLECULE
HYPERVALENT MOLECULE
Boy/Male
Finnish, Indian, Sanskrit
Molecule; Particle; Earth; Born of Dust
Girl/Female
African, Bengali, Gujarati, Hindu, Indian, Kannada, Kenyan, Malayalam, Marathi, Sanskrit, Sindhi, Tamil, Telugu
Small; Atom; Black; Molecule; Seed
HYPERVALENT MOLECULE
HYPERVALENT MOLECULE
Surname or Lastname
English
English : variant spelling of Pearsall or Purcell.
Girl/Female
Greek American Gaelic English Hawaiian Irish
Light.
Surname or Lastname
English
English : nickname for someone thought to resemble the loach (a species of freshwater fish), Middle English loche.
Female
Hebrew
(דּï‹×“Ö´×™) Hebrew name DODI means "my beloved, my friend." Compare with another form of Dodi.
Girl/Female
Swedish
Graceful Christian.
Girl/Female
Muslim/Islamic
Bride
Male
German
Low German form of Latin Georgius, J�RGEN means "earth-worker, farmer."
Male
Croatian
, Bel's prince.
Boy/Male
Arabic
Sweet; Tiger; Brave
Boy/Male
Gujarati, Hindu, Indian, Kannada, Malayalam, Marathi, Sindhi, Telugu, Traditional
Lord of Knowledge
HYPERVALENT MOLECULE
HYPERVALENT MOLECULE
HYPERVALENT MOLECULE
HYPERVALENT MOLECULE
HYPERVALENT MOLECULE
a.
Capable of neutralizing four molecules of a monobasic acid; having four hydrogen atoms capable of replacement ba acids or acid atoms; -- said of certain bases; thus, erythrine, C4H6(OH)4, is a tetracid alcohol.
n.
A light oily hydrocarbon, C14H30, of the marsh-gas series; -- so called from the fourteen carbon atoms in the molecule.
n.
A hypothetical hydrocarbon, C4H4, analogous to benzene; -- so called from the four carbon atoms in the molecule.
a.
Capable of neutralizing three molecules of a monobasic acid or the equivalent; having three hydrogen atoms which may be acid radicals; -- said of certain bases; thus, glycerin is a triacid base.
n.
A nitrate formed from three molecules of nitric acid; also, less properly, applied to certain basic nitrates; as, trisnitrate of bismuth.
n.
A group of atoms so united and combined by chemical affinity that they form a complete, integrated whole, being the smallest portion of any particular compound that can exist in a free state; as, a molecule of water consists of two atoms of hydrogen and one of oxygen. Cf. Atom.
n.
An oxide having four atoms of oxygen in the molecule; a quadroxide; as, osmium tetroxide, OsO/.
n.
One who holds the doctrine that the space between the bodies of the universe, or the molecules and atoms of matter., is a vacuum; -- opposed to plenist.
a.
Capable of neutralizing three molecules of a monacid base, or their equivalent; having three hydrogen atoms capable of replacement by basic elements on radicals; -- said of certain acids; thus, citric acid is a tribasic acid.
v. i.
A vibration propagated from particle to particle through a body or elastic medium, as in the transmission of sound; an assemblage of vibrating molecules in all phases of a vibration, with no phase repeated; a wave of vibration; an undulation. See Undulation.
a.
Consisting of four atoms; having four atoms in the molecule, as phosphorus and arsenic.
a.
Capable of neutralizing four molecules of a monacid base; having four hydrogen atoms capable of replacement by bases; quadribasic; -- said of certain acids; thus, normal silicic acid, Si(OH)4, is a tetrabasic acid.
n.
Butylene; -- so called from the four carbon atoms in the molecule.
n.
A chloride having three atoms of chlorine in the molecule.
a.
Containing, or consisting of, three different parts, as elements, atoms, groups, or radicals, which are regarded as having different functions or relations in the molecule; thus, sodic hydroxide, NaOH, is a ternary compound.
n.
A hydrocarbon, C23H48, of the methane series, resembling paraffin; -- so called because it has twenty-three atoms of carbon in the molecule.
n.
A liquid hydrocarbon, C11H24, of the methane series, found in petroleum; -- so called from its containing eleven carbon atoms in the molecule.
n.
A palmitate derived from three molecules of palmitic acid.
n.
Butyl; -- so called from the four carbon atoms in the molecule.
n.
A hydrocarbon, C24H50, resembling paraffin, and like it belonging to the marsh-gas series; -- so called from having twenty-four atoms of carbon in the molecule.