Functionality (chemistry)

Last updated
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.

Related Research Articles

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

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

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

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical study.

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

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

<span class="mw-page-title-main">Conjugated system</span> System of connected p-orbitals with delocalized electrons in a molecule

In theoretical chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases stability. It is conventionally represented as having alternating single and multiple bonds. Lone pairs, radicals or carbenium ions may be part of the system, which may be cyclic, acyclic, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.

In organic chemistry, a substituent is one or a group of atoms that replaces atoms, thereby becoming a moiety in the resultant (new) molecule.

In chemistry, an acetylide is a compound that can be viewed as the result of replacing one or both hydrogen atoms of acetylene (ethyne) HC≡CH by metallic or other cations. The term is also used, more loosely, for any compound obtained in the same way from an acetylene derivative RC≡CH, where R is some organic side chain.

In chemistry, the valence or valency of an atom is a measure of its combining capacity with other atoms when it forms chemical compounds or molecules. Valence is generally understood to be the number of chemical bonds that each atom of a given chemical element typically forms. Double bonds are considered to be two bonds, triple bonds to be three, quadruple bonds to be four, quintuple bonds to be five and sextuple bonds to be six. In most compounds, the valence of hydrogen is 1, of oxygen is 2, of nitrogen is 3, and of carbon is 4. Valence is not to be confused with the related concepts of the coordination number, the oxidation state, or the number of valence electrons for a given atom.

<span class="mw-page-title-main">Michael addition reaction</span> Reaction in organic chemistry

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor and a Michael acceptor to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

<span class="mw-page-title-main">Chain-growth polymerization</span> Polymerization technique

Chain-growth polymerization (AE) or chain-growth polymerisation (BE) is a polymerization technique where monomer molecules add onto the active site on a growing polymer chain one at a time. There are a limited number of these active sites at any moment during the polymerization which gives this method its key characteristics.

<span class="mw-page-title-main">Branching (polymer chemistry)</span> Attachment of side chains to the backbone chain of a polymer

In polymer chemistry, branching is the regular or irregular attachment of side chains to a polymer's backbone chain. It occurs by the replacement of a substituent on a monomer subunit by another covalently-bonded chain of that polymer; or, in the case of a graft copolymer, by a chain of another type. Branched polymers have more compact and symmetrical molecular conformations, and exhibit intra-heterogeneous dynamical behavior with respect to the unbranched polymers. In crosslinking rubber by vulcanization, short sulfur branches link polyisoprene chains into a multiple-branched thermosetting elastomer. Rubber can also be so completely vulcanized that it becomes a rigid solid, so hard it can be used as the bit in a smoking pipe. Polycarbonate chains can be crosslinked to form the hardest, most impact-resistant thermosetting plastic, used in safety glasses.

In polymer chemistry, chain termination is any chemical reaction that ceases the formation of reactive intermediates in a chain propagation step in the course of a polymerization, effectively bringing it to a halt.

In organic chemistry, umpolung or polarity inversion is the chemical modification of a functional group with the aim of the reversal of polarity of that group. This modification allows secondary reactions of this functional group that would otherwise not be possible. The concept was introduced by D. Seebach and E.J. Corey. Polarity analysis during retrosynthetic analysis tells a chemist when umpolung tactics are required to synthesize a target molecule.

<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.

<span class="mw-page-title-main">Living free-radical polymerization</span>

Living free radical polymerization is a type of living polymerization where the active polymer chain end is a free radical. Several methods exist. IUPAC recommends to use the term "reversible-deactivation radical polymerization" instead of "living free radical polymerization", though the two terms are not synonymous.

In organosilicon chemistry, 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 [R2Si−NR]n occur. R can be hydrogen atoms or organic substituents. If all substituents R are hydrogen 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 [R2Si−NH]n are isoelectronic with and close relatives to polysiloxanes [R2Si−O]n (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> Molecular architecture consisting of an inner space within an external frame

In host–guest chemistry, macromolecular cages are a type of macromolecule structurally consisting of a three-dimensional chamber 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