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Bonding halogens

The same Lewis acid type nature of the iodine atom is also demonstrated in fluorovinyl iodide (15), which makes crystals 17 and 19, respectively, with N,N,N,N-tetramethylethylene [Pg.27]

A strict alignment of electron donor module through the halogen bonding can be used for stereo-controlled [2 + 2] photochemical cycloaddition in a solid state. A combination of [Pg.30]


The halogens F Cl Br and I do not differ much in their preference for the equatorial position As the atomic radius increases in the order F < Cl < Br < I so does the carbon-halogen bond dis tance and the two effects tend to cancel... [Pg.123]

The carbon that bears the functional group is sp hybridized m alcohols and alkyl halides Figure 4 1 illustrates bonding m methanol The bond angles at carbon are approximately tetrahedral as is the C—O—H angle A similar orbital hybridization model applies to alkyl halides with the halogen connected to sp hybridized carbon by a ct bond Carbon-halogen bond distances m alkyl halides increase m the order C—F (140 pm) < C—Cl (179 pm) < C—Br (197 pm) < C—I (216 pm)... [Pg.146]

Carbon-oxygen and carbon-halogen bonds are polar covalent bonds and carbon bears a partial positive charge in alcohols ( " C—0 ) and in alkyl halides ( " C—X ) Alcohols and alkyl halides are polar molecules The dipole moments of methanol and chloromethane are very similar to each other and to water... [Pg.147]

Relatively simple notions of attractive forces between opposite charges are suffi cient to account for many of the properties of chemical substances You will find it help ful to keep the polarity of carbon-oxygen and carbon-halogen bonds m mind as we develop the properties of alcohols and alkyl halides m later sections... [Pg.147]

The rate of elimination depends on the halogen the reactivity of alkyl halides increasing with decreasing strength of the carbon-halogen bond... [Pg.214]

What are the implications of the effects of the various halide leaving groups Because the halogen with the weakest bond to carbon reacts fastest Ingold concluded that the carbon-halogen bond breaks m the rate determining step The weaker the carbon-halogen bond the easier it breaks... [Pg.214]

The E2 mechanism is a concerted process m which the carbon-hydrogen and carbon-halogen bonds both break m the same elementary step What if these bonds break m separate steps s... [Pg.217]

Step (1) Alkyl halide dissociates by heterolytic cleavage of carbon-halogen bond (Ionization step)... [Pg.218]

One possibility is the two step mechanism of Figure 5 12 m which the carbon-halogen bond breaks first to give a carbocation intermediate followed by depro tonation of the carbocation m a second step... [Pg.218]

The alkyl halide m this case 2 bromo 2 methylbutane ionizes to a carbocation and a halide anion by a heterolytic cleavage of the carbon-halogen bond Like the dissoci ation of an aUcyloxonmm ion to a carbocation this step is rate determining Because the rate determining step is ummolecular—it involves only the alkyl halide and not the base—It is a type of El mechanism... [Pg.218]

Because the carbon-halogen bond breaks m the slow step the rate of the reaction depends on the leaving group Alkyl iodides have the weakest carbon-halogen bond and are the most reactive alkyl fluorides have the strongest carbon-halogen bond and are the least reactive... [Pg.219]

The carbon-halogen bond in an alkyl halide is polar... [Pg.327]

Secondary alkyl halides react by a similar mechanism involving attack on benzene by a secondary carbocation Methyl and ethyl halides do not form carbocations when treated with aluminum chloride but do alkylate benzene under Friedel-Crafts conditions The aluminum chloride complexes of methyl and ethyl halides contain highly polarized carbon-halogen bonds and these complexes are the electrophilic species that react with benzene... [Pg.482]

The value of alkyl halides as starting materials for the preparation of a variety of organic functional groups has been stressed many times In our earlier discussions we noted that aryl halides are normally much less reactive than alkyl halides m reactions that involve carbon-halogen bond cleavage In the present chapter you will see that aryl halides can exhibit their own patterns of chemical reactivity and that these reac tions are novel useful and mechanistically interesting... [Pg.971]

The carbon-halogen bonds of aryl halides are both shorter and stronger than the carbon-halogen bonds of alkyl halides In this respect as well as m their chemical behavior they resemble vinyl halides more than alkyl halides A hybridization effect seems to be responsible because as the data m Table 23 1 indicate similar patterns are seen for both carbon-hydrogen bonds and carbon-halogen bonds An increase m s... [Pg.971]

The strength of their carbon-halogen bonds causes aryl halides to react very slowly in reactions in which carbon-halogen bond cleavage is rate determining as m nude ophilic substitution for example Later m this chapter we will see examples of such reactions that do take place at reasonable rates but proceed by mechanisms distinctly dif ferent from the classical S l and 8 2 pathways... [Pg.972]

Aryl halides are compounds of the type Ar—X where X = F Cl Br or I The carbon-halogen bond is stronger m ArX than m an alkyl halide (RX)... [Pg.986]

Ketene Insertions. Ketenes insert into strongly polarized or polarizable single bonds, such as reactive carbon—halogen bonds, giving acid hahdes (7) and into active acid haUdes giving haUdes of p-ketoacids (8) (46). Phosgene [77-44-5] (47) and thiophosgene [463-71-8] (48) also react with ketenes. [Pg.475]

Silicon halides are typically tetrahedral compounds. The siUcone—halogen bond is very polar thus the siUcon is susceptible to nucleophilic attack, which in part accounts for the broad range of reactivity with various chemicals. Furthermore, reactivity generally increases with the atomic weight of the halogen atom. [Pg.18]


See other pages where Bonding halogens is mentioned: [Pg.50]    [Pg.327]    [Pg.328]    [Pg.93]    [Pg.180]    [Pg.182]    [Pg.567]    [Pg.179]    [Pg.214]    [Pg.215]    [Pg.215]    [Pg.240]    [Pg.327]    [Pg.351]    [Pg.975]    [Pg.979]    [Pg.289]    [Pg.362]    [Pg.362]    [Pg.362]    [Pg.263]    [Pg.452]    [Pg.39]    [Pg.81]    [Pg.67]    [Pg.91]    [Pg.425]    [Pg.145]    [Pg.558]    [Pg.6]   
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Activation of Carbon-Halogen Bonds

Addition of Halogens to Double Bonds

Addition reactions C—halogen bond formation

Alkenes halogen-bond basicity

Alkyl halides polar carbon-halogen bonds

Amines halogen-bond basicity

Anilines halogen bonds

Anion transport, halogen bonds

Aromatic carbon-halogen bond, cleavage

Aromatic-halogen bond formation

Arsenic—phosphorus bonds elemental halogens

Arsenic—sulfur bonds elemental halogens

Aryl halides carbon-halogen bond

Atom transfer radical polymerization carbon—halogen bond

BDEs of C-halogen bonds

Bismuth—carbon bonds elemental halogens

Blue Shift of the Visible Diiodine Transition Upon Halogen Bonding to Pyridines

Bond Dissociation Energy Halogenation

Bond cleavage carbon-halogen

Bond dissociation energy and halogenation of methane

Bond dissociation energy halogen diatomics

Bond energy halogens

Bond strengths, carbon-halogen

Bond, dative halogen compounds

Bonding carbon-halogen bond scission

Bonding halogen atom

Bonds antimony-halogen

Bonds arsenic-halogen

Bonds carbon-halogen bond

Bonds to Halogen

Bonds to Sulphur, Phosphorus, Nitrogen and Halogens

Boron-halogen bond

Boron-mercury bonds halogens

Bromine halogen-bonded compounds

B—halogen bonds

C-Halogen Bond Formations

Carbon and Metal-Halogen Bonds

Carbon-Halogen Bond Formation with Group 11 Metals

Carbon-halogen bond activation

Carbon-halogen bond dipole moment

Carbon-halogen bond dissociation

Carbon-halogen bond dissociation energies

Carbon-halogen bond fission

Carbon-halogen bond formation

Carbon-halogen bond formation bromine

Carbon-halogen bond formation chlorine

Carbon-halogen bond formation fluorine

Carbon-halogen bond formation iodine

Carbon-halogen bond forming reactions

Carbon-halogen bond lengths

Carbon-halogen bond polarity

Carbon-halogen bond scission

Carbon-halogen bond, hydrogenolysis

Carbon-halogen bond, polar

Carbon-halogen bond, reaction number

Carbon-halogen bonds

Carbon-halogen bonds catalytic reduction

Carbon-halogen bonds reactivity order

Carbon-halogen bonds reduction

Carbon-halogen bonds reductive cleavage

Carbon-halogen bonds, photochemical reactions

Carbon-halogen bonds, reductive metal

Carbon-halogen bonds, reductive metal insertion

Carbon-hydrogen bonds halogenation

Carbon—lead bonds elemental halogens

Carbon—magnesium bonds elemental halogens

Carbon—nitrogen bonds elemental halogens

Carbon—phosphorus bonds elemental halogens

Carbon—selenium bonds halogens

Carbon—silicon bonds elemental halogens

Carbon—sulfur bonds halogens

Catalytic Reactions Involving Carbon-Halogen Bond Cleavage

Chalcogen-halogen secondary bonds

Chlorine halogen-bonded compounds

Cleavage of Carbon Halogen Bonds

Complexes with M-P-Halogen Bonds

Containing metal-halogen bonds

Dihalo- and monohalocarbene complexes carbon-halogen bond

Dihalocarbene complexes carbon-halogen bond

Dihalogens halogen bonding

Double bonds, halogenation

Electron transfer reduction C—halogen bonds

Electrostatic potential, molecular interactive halogen bonding

Expanding the palette of supramolecular interactions from H-bonding to Li-, halogen, pnictogen, chalcogen and tetrel binding

Force constant carbon-halogen bond

Formation of C-halogen bonds

Formation of carbon-halogen bonds

Formation of the nitrogen-halogen bond

Gold-halogen bonds

Halides and Halogen Atoms as Hydrogen-Bond Acceptors

Halides carbon-halogen bond cleavage

Halides carbon-halogen bond reaction number

Halogen Bond Fission

Halogen Bonding and Other Interactions

Halogen antimony—hydrogen bonds

Halogen bond lengths

Halogen bonding bond geometry

Halogen bonding lengths

Halogen bonding stretching-force constants

Halogen bonding, interactions

Halogen bonds

Halogen bonds, hydrogenolysis

Halogen bonds, reductive cleavage

Halogen bonds/bonding

Halogen bonds/bonding

Halogen carbon—bismuth bonds

Halogen complexes bond formation

Halogen nitrogen—sulfur bonds

Halogen phosphorus—oxygen bonds

Halogen selenium—oxygen bonds

Halogen silicon—nitrogen bonds

Halogen silicon—oxygen bonds

Halogen silicon—phosphorus bonds

Halogen sulfur—oxygen bonds

Halogen surface bond

Halogen tellurium—oxygen bonds

Halogen-Containing Bonds

Halogen-bond basicities

Halogen-bond donating tendencies

Halogen-bond-based Assembly Strategies

Halogen-bonded co-crystals

Halogen-bonded supramolecular

Halogen-bonded supramolecular architectures

Halogen-bonding-based supramolecular

Halogen-nitrogen single bonds

Halogen-silicon bonds

Halogen-silicon bonds dissociation energies

Halogen-silicon bonds lengths

Halogenated alkyl radical additions to double and triple bonds

Halogenation, of double bonds

Halogens, elemental bonds

Halogens, elemental carbon—selenium bonds

Halogens, elemental carbon—sulfur bonds

Halogens, hydrogen bonds

Halogens, labile bonded

Halomethanes, carbon-halogen bonds

Hydrogen Bonds to Halogens

Hydrogen bonding to halogens

Hydrogenolysis of C-Halogen Bonds

Hydrogenolysis of carbon-halogen bonds

Infrared spectroscopy halogen-bond complexes

Insertion reactions carbon-halogen bonds

Iodine halogen-bonded complexes

Lead—halogen bonds

Lead—halogen bonds complex hydrides

Lead—halogen bonds metal hydrides

Lead—halogen bonds reactions with

Liquid crystals, halogen-bonded

Magnesium-halogen bonds

Metal atoms with carbon-halogen bonds

Metal-halogen bonds

Metal-halogen bonds, (continued

N-halogen bonds

Nitrogen—oxygen bonds elemental halogens

Nitrogen—phosphorus bonds elemental halogens

Nitrogen—selenium bonds elemental halogens

Nitrogen—silicon bonds elemental halogens

Nitrogen—sulfur bonds elemental halogens

O-halogen bonds

Oxidation carbon-halogen bonds

Oxidative addition of the carbon-halogen bond

Oxygen—selenium bonds elemental halogens

Oxygen—silicon bonds elemental halogens

Oxygen—sulfur bonds elemental halogens

Phosphorus-halogen bond

Phosphorus—hydrogen bonds elemental halogens

Phosphorus—silicon bonds elemental halogens

Phosphorus—sulfur bonds elemental halogens

Radial geometries, halogen-bonded

Reactions into Element-Halogen Bonds

Reactions of Alkanes Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity

Reactions of Carbon-Halogen Bonds

Reduction C—halogen bonds

Reduction of Carbon-Halogen Bonds

Relaxation in Molecules or Ions With Covalently Bonded Halogens

S-halogen bonds

Selenocyanates halogen-bonded

Silicon-halogen bond strengths

Silicon-transition metal bonds halogens

Silicon—sulfur bonds halogens

Sonolysis of the carbon-halogen bond

Structure of Halogen-Bonded Complexes

The Polar Carbon-Halogen Bond

Thiocyanates, halogen-bonded

Tin-halogen bonds

Transition metal-halogen bonds, insertion

Transporter, halogen-bonding

With phosphorus-halogen bonds

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