Dianin's compound (4-''p''-hydroxyphenyl-2,2,4-trimethylchroman) was first prepared by
Aleksandr Dianin
Aleksandr Pavlovich Dianin (russian: Александр Павлович Дианин; 20 April 1851 – 6 December 1918) was a Russian chemist from Saint Petersburg. He carried out studies on phenols and discovered a phenol derivative now known ...
in 1914. This compound is a
condensation
Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapo ...
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Is ...
of
bisphenol A
Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial ...
and
acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscibl ...
and of special importance in
host–guest chemistry In supramolecular chemistry, host–guest chemistry describes complexes that are composed of two or more molecules or ions that are held together in unique structural relationships by forces other than those of full covalent bonds. Host–guest ch ...
because it can form a large variety of
clathrate
A clathrate is a chemical substance consisting of a lattice that traps or contains molecules. The word ''clathrate'' is derived from the Latin (), meaning ‘with bars, latticed’. Most clathrate compounds are polymeric and completely envelo ...
s with suitable guest molecules. One example is the clathrate of Dianin's compound with
morpholine
Morpholine is an organic chemical compound having the chemical formula O( C H2CH2)2 NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. Fo ...
.
Slow evaporation of a solution containing both
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. Th ...
s yields crystals. Each asymmetric
unit cell
In geometry, biology, mineralogy and solid state physics, a unit cell is a repeating unit formed by the vectors spanning the points of a lattice. Despite its suggestive name, the unit cell (unlike a unit vector, for example) does not necessaril ...
making up the crystal contains six chroman molecules of which two are deprotonated and two
protonated morpholine molecules. The six chroman molecules are
racemate
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...
pairs.
References
{{Reflist
Clathrates
Phenols
Russian inventions
Chromanes