An auxochrome (from

Ancient Greek Ancient Greek includes the forms of the Greek language used in ancient Greece and the ancient world from around 1500 BC to 300 BC. It is often roughly divided into the following periods: Mycenaean Greek (), Dark Ages (), the Archaic peri ...

''auxanō'' "increase" and ''chrōma'' "colour") is a group of atoms attached to a

chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the molec ...

which modifies the ability of that chromophore to absorb light. They themselves fail to produce the colour; but when present along with the chromophores in an organic compound intensifies the colour of the

chromogen In chemistry, the term chromogen refers to a colourless (or faintly coloured) chemical compound that can be converted by chemical reaction into a compound which can be described as "coloured". There is no universally agreed definition of the term. ...

. Examples include the

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...

(−OH), the

amino group In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such a ...

(−NH₂), the

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

group (−CHO), and the

methyl mercaptan Methanethiol (also known as methyl mercaptan) is an organosulfur compound with the chemical formula . It is a colorless gas with a distinctive putrid smell. It is a natural substance found in the blood, brain and feces of animals (including huma ...

group (−SCH₃). An auxochrome is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

of atoms with one or more

lone pair In chemistry, a lone pair refers to a pair of valence electrons that are not shared with another atom in a covalent bondIUPAC ''Gold Book'' definition''lone (electron) pair''/ref> and is sometimes called an unshared pair or non-bonding pair. Lone ...

s of electrons when attached to a chromophore, alters both the

wavelength In physics, the wavelength is the spatial period of a periodic wave—the distance over which the wave's shape repeats. It is the distance between consecutive corresponding points of the same phase on the wave, such as two adjacent crests, tro ...

and intensity of

absorption Absorption may refer to: Chemistry and biology * Absorption (biology), digestion **Absorption (small intestine) *Absorption (chemistry), diffusion of particles of gas or liquid into liquid or solid materials *Absorption (skin), a route by which ...

. If these groups are in direct

conjugation Conjugation or conjugate may refer to: Linguistics * Grammatical conjugation, the modification of a verb from its basic form * Emotive conjugation or Russell's conjugation, the use of loaded language Mathematics * Complex conjugation, the chang ...

with the pi-system of the chromophore, they may increase the wavelength at which the light is absorbed and as a result intensify the absorption. A feature of these auxochromes is the presence of at least one

of electrons which can be viewed as extending the conjugated system by

resonance Resonance describes the phenomenon of increased amplitude that occurs when the frequency of an applied periodic force (or a Fourier component of it) is equal or close to a natural frequency of the system on which it acts. When an oscillatin ...

Effects on chromophore

It increases the color of any

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

. For example,

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

does not display color as it does not have a chromophore; but

nitrobenzene Nitrobenzene is an organic compound with the chemical formula C6H5 NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor t ...

is pale yellow color because of the presence of a

nitro group In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitr ...

(−NO₂) which acts as a chromophore. But ''p''-hydroxynitrobenzene exhibits a deep yellow color, in which the −OH group acts as an auxochrome. Here the auxochrome (−OH) is conjugated with the chromophore −NO₂. Similar behavior is seen in

azobenzene Azobenzene is a photoswitchable chemical compound composed of two phenyl rings linked by a N=N double bond. It is the simplest example of an aryl azo compound. The term 'azobenzene' or simply 'azo' is often used to refer to a wide class of simi ...

which has a red color, but ''p''-hydroxyazobenzene is dark red in color. The presence of an auxochrome in the

molecule is essential to make a

dye A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution an ...

. However, if an auxochrome is present in the meta position to the chromophore, it does not affect the color. An auxochrome is known as a compound that produces a

bathochromic shift Bathochromic shift (from Greek βαθύς ''bathys'', "deep"; and χρῶμα ''chrōma'', "color"; hence less common alternate spelling "bathychromic") is a change of spectral band position in the absorption, reflectance, transmittance, or emissi ...

, also known as red shift because it increases the wavelength of absorption, therefore moving closer to

infrared light Infrared (IR), sometimes called infrared light, is electromagnetic radiation (EMR) with wavelengths longer than those of visible light. It is therefore invisible to the human eye. IR is generally understood to encompass wavelengths from around ...

. Woodward−Fieser rules estimate the shift in wavelength of maximum absorption for several auxochromes attached to a

conjugated system 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 ...

in an organic molecule. An auxochrome helps a dye to bind to the object that is to be colored.

Electrolytic dissociation An electrolyte is a medium containing ions that is electrically conducting through the movement of those ions, but not conducting electrons. This includes most soluble salts, acids, and bases dissolved in a polar solvent, such as water. Upon di ...

of the auxochrome group helps in binding and it is due to this reason a

basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version was created by John G. Kemeny and Thomas E. Kurtz at Dartmouth College ...

substance takes an

acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

ic dye.

Explanation for the colour modification

A molecule exhibits colour because it absorbs colours only of certain frequencies and reflects or transmits others. They are capable of absorbing and emitting light of various frequencies. Light waves with frequency very close to their

natural frequency Natural frequency, also known as eigenfrequency, is the frequency at which a system tends to oscillate in the absence of any driving force. The motion pattern of a system oscillating at its natural frequency is called the normal mode (if all par ...

are absorbed readily. This phenomenon, known as

, means that the molecule can absorb radiation of a particular frequency which is the same as the frequency of electron movement within the molecule. The chromophore is the part of the molecule where the energy difference between two different

molecular orbitals In chemistry, a molecular orbital is a mathematical function describing the location and wave-like behavior of an electron in a molecule. This function can be used to calculate chemical and physical properties such as the probability of finding ...

falls within the range of the

visible spectrum The visible spectrum is the portion of the electromagnetic spectrum that is visual perception, visible to the human eye. Electromagnetic radiation in this range of wavelengths is called ''visible light'' or simply light. A typical human eye wil ...

and hence absorbs some particular colours from visible light. Hence the molecule appears coloured. When auxochromes are attached to the molecule, the natural frequency of the chromophore gets changed and thus the colour gets modified. Different auxochromes produce different effects in the chromophore which in turn causes absorption of light from other parts of the spectrum. Normally, auxochromes which intensify the colour are chosen.{{cite journal , title=The Dye Spectrum , url=https://books.google.com/books?id=TaGZ6a_ZXEcC&q=Chromophore&pg=PA52-IA2 , journal=New Scientist , date=May 1989 , volume=122 , issue=1665 , pages=52 , issn=0262-4079 , publisher=Reed Business Information

Classification

There are mainly two types of auxochromes: *

Acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

ic: −COOH, −OH, −SO₃H *

Basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version was created by John G. Kemeny and Thomas E. Kurtz at Dartmouth College ...

: −NH₂, −NHR, −NR₂

References

Chemical compounds Color Chemical reactions