Functionality (chemistry)

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Monofunctional compounds
Methyl-Acetate Structural Formula V1.svg

Methyl acetate

Thiophenol Structural Formula V1.svg

Thiophenol

Ethyl Amine Structural Formula V1.svg

Ethylamine

Difunctional compounds
Malonic Acid Structural Formula V1.svg

Malonic acid

2-Aminoethanol Structural Formula V1.svg

Ethanolamine

Glycine Structural Formula V1.svg

Glycine

Trifunctional compounds
Glycerine Structural Formula V1.svg

Glycerol

(R)-Cysteine Structural Formula V1.svg

(R)-Cysteine

In chemistry, functionality is the presence of functional groups in a molecule. A monofunctional molecule possesses one functional group, a bifunctional (or difunctional) two, a trifunctional three, and so forth. In organic chemistry (and other fields of chemistry), a molecule's functionality has a decisive influence on its reactivity.

Contents

In polymer chemistry, the functionality of a monomer refers to its number of polymerizable groups, and affects the formation and the degree of crosslinking of polymers.

In organic chemistry and material science

In organic chemistry, functionality is often used as a synonym for functional group. For example, a hydroxyl group can also be called a HO-function. [1] [2]

Functionalisation means the introduction of functional groups, for example

In polymer chemistry

According to IUPAC, the functionality of a monomer is defined as the number of bonds that a monomer's repeating unit forms in a polymer with other monomers. Thus in the case of a functionality of f = 2 a linear polymer is formed by polymerizing (a thermoplastic). Monomers with a functionality f ≥ 3 lead to a branching point, which can lead to cross-linked polymers (a thermosetting polymer). Monofunctional monomers do not exist as such molecules lead to a chain termination. [6]

From the average functionality of the used monomers the reaching of the gel point can be calculated as a function of reaction progress. [7] Side reactions may increase or decrease the functionality. [8]

However, IUPAC definition and the use of the term in organic chemistry differ with respect to the functionality of a double bond. [6] [9] In polymer chemistry, a double bond possesses a functionality of two (because two points of contact for further polymer chains are present, on each of the two adjacent carbon atoms), while in organic chemistry the double bond is a functional group and thus has a functionality of one.

See also

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<span class="mw-page-title-main">Chemical reaction</span> Process that results in the interconversion of chemical species

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<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

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<span class="mw-page-title-main">Organic chemistry</span> Subdiscipline of chemistry, focusing on carbon compounds

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<span class="mw-page-title-main">Organometallic chemistry</span> Study of organic compounds containing metal(s)

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<span class="mw-page-title-main">Polymer</span> Substance composed of macromolecules with repeating structural units

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<span class="mw-page-title-main">Nanoporous materials</span>

Nanoporous materials consist of a regular organic or inorganic bulk phase in which a porous structure is present. Nanoporous materials exhibit pore diameters that are most appropriately quantified using units of nanometers. The diameter of pores in nanoporous materials is thus typically 100 nanometers or smaller. Pores may be open or closed, and pore connectivity and void fraction vary considerably, as with other porous materials. Open pores are pores that connect to the surface of the material whereas closed pores are pockets of void space within a bulk material. Open pores are useful for molecular separation techniques, adsorption, and catalysis studies. Closed pores are mainly used in thermal insulators and for structural applications.

<span class="mw-page-title-main">Carbon nanotube chemistry</span>

Carbon nanotube chemistry involves chemical reactions, which are used to modify the properties of carbon nanotubes (CNTs). CNTs can be functionalized to attain desired properties that can be used in a wide variety of applications. The two main methods of CNT functionalization are covalent and non-covalent modifications.

Polysilazanes are polymers in which silicon and nitrogen atoms alternate to form the basic backbone. Since each silicon atom is bound to two separate nitrogen atoms and each nitrogen atom to two silicon atoms, both chains and rings of the formula occur. can be hydrogen atoms or organic substituents. If all substituents R are H atoms, the polymer is designated as Perhydropolysilazane, Polyperhydridosilazane, or Inorganic Polysilazane ([H2Si–NH]n). If hydrocarbon substituents are bound to the silicon atoms, the polymers are designated as Organopolysilazanes. Molecularly, polysilazanes are isoelectronic with and close relatives to Polysiloxanes (silicones).

<span class="mw-page-title-main">Two-dimensional polymer</span>

A two-dimensional polymer (2DP) is a sheet-like monomolecular macromolecule consisting of laterally connected repeat units with end groups along all edges. This recent definition of 2DP is based on Hermann Staudinger's polymer concept from the 1920s. According to this, covalent long chain molecules ("Makromoleküle") do exist and are composed of a sequence of linearly connected repeat units and end groups at both termini.

Fluorine forms a great variety of chemical compounds, within which it always adopts an oxidation state of −1. With other atoms, fluorine forms either polar covalent bonds or ionic bonds. Most frequently, covalent bonds involving fluorine atoms are single bonds, although at least two examples of a higher order bond exist. Fluoride may act as a bridging ligand between two metals in some complex molecules. Molecules containing fluorine may also exhibit hydrogen bonding. Fluorine's chemistry includes inorganic compounds formed with hydrogen, metals, nonmetals, and even noble gases; as well as a diverse set of organic compounds. For many elements the highest known oxidation state can be achieved in a fluoride. For some elements this is achieved exclusively in a fluoride, for others exclusively in an oxide; and for still others the highest oxidation states of oxides and fluorides are always equal.

<span class="mw-page-title-main">Macromolecular cages</span>

Macromolecular cages have three dimensional chambers surrounded by a molecular framework. Macromolecular cage architectures come in various sizes ranging from 1-50 nm and have varying topologies as well as functions. They can be synthesized through covalent bonding or self-assembly through non-covalent interactions. Most macromolecular cages that are formed through self-assembly are sensitive to pH, temperature, and solvent polarity.

References

  1. Kurt Peter C. Vollhardt, Neil Eric Schore: Organische Chemie, S. 73 ( , p. 74, at Google Books).
  2. Riedel: Moderne Anorganische Chemie von Christoph Janiak, S. 401 ( , p. 401, at Google Books).
  3. Alexander Langner, Anthony Panarello, Sandrine Rivillon, Oleksiy Vassylyev, Johannes G. Khinast, Yves J. Chabal: Controlled Silicon Surface Functionalization by Alkene Hydrosilylation, J. Am. Chem.
  4. Marie-Alexandra Neouze, Ulrich Schubert: Surface Modification and Functionalization of Metal and Metal Oxide Nanoparticles by Organic Ligands, Monatsh.
  5. Dirk Steinborn: Grundlagen der metallorganischen Komplexkatalyse, S. 305 ( , p. 239, at Google Books
  6. 1 2 Eintrag zu functionality, f of a monomer.
  7. Koltzenburg: Polymere: Synthese, Eigenschaften und Anwendungen, S. 187 ( , p. 188, at Google Books). This reference is being translated to English as "Polymer Chemistry" by the same authors, to appear in September 2017. See
  8. Hans-Georg Elias: Makromoleküle: Chemische Struktur und Synthesen, S. 468 und 477 ( , p. 468, at Google Books).
  9. IUPAC , Compendium of Chemical Terminology , 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006) " chemical functionality ". doi : 10.1351/goldbook.CT07503