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Carbocycles
Inorganic cyclic compounds
Heterocyclic compounds
Macrocycles
Nomenclature
Isomerism
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Stereochemistry
Conformational isomerism
Aromaticity
Principal uses
Synthetic reactions
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Important general reactions for forming rings
Ring-closing reactions
Ring-opening reactions
Ring expansion and ring contraction reactions
Examples
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Simple, mono-cyclic examples
Complex and polycyclic examples
See also
References
Further reading
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Cyclic compound

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From Wikipedia, the free encyclopedia
A cyclic compound (or ring compound) is a term for a compound in the field of
chemistry in which one or more series of atoms in the compound is connected to form
a ring. Rings may vary in size from three to many atoms, and include examples where
all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon
(inorganic cyclic compounds), or where both carbon and non-carbon atoms are present
(heterocyclic compounds). Depending on the ring size, the bond order of the
individual links between ring atoms, and their arrangements within the rings,
carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the
latter case, they may vary from being fully saturated to having varying numbers of
multiple bonds between the ring atoms. Because of the tremendous diversity allowed,
in combination, by the valences of common atoms and their ability to form rings,
the number of possible cyclic structures, even of small size (e.g., < 17 total
atoms) numbers in the many billions.

Cyclic compound examples: All-carbon (carbocyclic) and more complex natural cyclic
compounds
Ingenol, a complex, terpenoid natural product, related to but simpler than the
paclitaxel that follows, which displays a complex ring structure including 3-, 5-,
and 7-membered non-aromatic, carbocyclic rings.
Ingenol, a complex, terpenoid natural product, related to but simpler than the
paclitaxel that follows, which displays a complex ring structure including 3-, 5-,
and 7-membered non-aromatic, carbocyclic rings.
Cycloalkanes, the simplest carbocycles, including cyclopropane, cyclobutane,
cyclopentane, and cyclohexane. Note, elsewhere an organic chemistry shorthand is
used where hydrogen atoms are inferred as present to fill the carbon's valence of 4
(rather than their being shown explicitly).
Cycloalkanes, the simplest carbocycles, including cyclopropane, cyclobutane,
cyclopentane, and cyclohexane. Note, elsewhere an organic chemistry shorthand is
used where hydrogen atoms are inferred as present to fill the carbon's valence of 4
(rather than their being shown explicitly).

Paclitaxel, another complex, plant-derived terpenoid, also a natural product,

displaying a complex multi-ring structure including 4-, 6-, and 8-membered rings
(carbocyclic and heterocyclic, aromatic and non-aromatic).
Paclitaxel, another complex, plant-derived terpenoid, also a natural product,
displaying a complex multi-ring structure including 4-, 6-, and 8-membered rings
(carbocyclic and heterocyclic, aromatic and non-aromatic).

Adding to their complexity and number, closing of atoms into rings may lock
particular atoms with distinct substitution (by functional groups) such that
stereochemistry and chirality of the compound results, including some
manifestations that are unique to rings (e.g., configurational isomers). As well,
depending on ring size, the three-dimensional shapes of particular cyclic
structures – typically rings of five atoms and larger – can vary and interconvert
such that conformational isomerism is displayed. Indeed, the development of this
important chemical concept arose historically in reference to cyclic compounds.
Finally, cyclic compounds, because of the unique shapes, reactivities, properties,
and bioactivities that they engender, are the majority of all molecules involved in
the biochemistry, structure, and function of living organisms, and in man-made
molecules such as drugs, pesticides, etc.

Structure and classification

A cyclic compound or ring compound is a compound in which at least some its atoms
are connected to form a ring.[1] Rings vary in size from three to many tens or even
hundreds of atoms. Examples of ring compounds readily include cases where:

all the atoms are carbon (i.e., are carbocycles),

none of the atoms are carbon (inorganic cyclic compounds),[2] or where
both carbon and non-carbon atoms are present (heterocyclic compounds).
Common atoms can (as a result of their valences) form varying numbers of bonds, and
many common atoms readily form rings. In addition, depending on the ring size, the
bond order of the individual links between ring atoms, and their arrangements
within the rings, cyclic compounds may be aromatic or non-aromatic; in the case of
non-aromatic cyclic compounds, they may vary from being fully saturated to having
varying numbers of multiple bonds. As a consequence of the constitutional
variability that is thermodynamically possible in cyclic structures, the number of
possible cyclic structures, even of small size (e.g., <17 atoms) numbers in the
many billions.[3]

Moreover, the closing of atoms into rings may lock particular functional group–
substituted atoms into place, resulting in stereochemistry and chirality being
associated with the compound, including some manifestations that are unique to
rings (e.g., configurational isomers);[4] As well, depending on ring size, the
three-dimensional shapes of particular cyclic structures — typically rings of five
atoms and larger — can vary and interconvert such that conformational isomerism is
displayed.[4]

Carbocycles
The vast majority of cyclic compounds are organic, and of these, a significant and
conceptually important portion are composed of rings made only of carbon atoms
(i.e., they are carbocycles).[citation needed]

Inorganic cyclic compounds

Inorganic atoms form cyclic compounds as well. Examples include sulfur (e.g. in
polysulfides), silicon (e.g., in silanes), phosphorus (e.g., in phosphanes,
metaphosphates and other phosphoric acid derivatives), and boron (e.g., sodium
metaborate).[citation needed] When carbon in benzene is "replaced" by other
elements, e.g., as in borabenzene, silabenzene, germanabenzene, stannabenzene, and
phosphorine, aromaticity is retained, and so aromatic inorganic cyclic compounds
are also known and well-characterized.[citation needed]

Heterocyclic compounds
Cyclic compounds that have both carbon and non-carbon atoms present are termed
heterocyclic compounds;[citation needed] alternatively the name can refer to
inorganic cyclic compounds, such as siloxanes and borazines, that have more than
one type of atom in their rings.[citation needed] Hantzsch–Widman nomenclature is
recommended by the IUPAC for naming heterocycles, but many common names remain in
regular use.[citation needed]

Macrocycles
Cycloctane conformations.jpg
The term macrocycle is used for compounds having a rings of 8 or more atoms.[5][6]
Macrocycles may be fully carbocyclic, heterocyclic but having limited heteroatoms
(e.g., in lactones and lactams), or be rich in heteroatoms and displaying
significant symmetry (e.g., in the case of chelating macrocycles). Macrocycles can
access a number of stable conformations, with preference to reside in conformations
that minimize transannular nonbonded interactions within the ring (e.g., with the
chair and chair-boat being more stable than the boat-boat conformation for
cyclooctane, because of the interactions depicted by the arcs shown).[citation
needed] Medium rings (8-11 atoms) are the most strained, with between 9-13
(kcal/mol) strain energy, and analysis of factors important in the conformations of
larger macrocycles can be modeled using medium ring conformations.[7]
Conformational analysis of odd-membered rings suggests they tend to reside in less
symmetrical forms with smaller energy differences between stable conformations.[8]

Chelating macrocyclic structures of interest in inorganic and supramolecular

chemistry, an example array. A, the crown ether, 18-crown-6; B, the simple tetra-
aza chelator, cyclam; C, an example porphyrin, the unsubstituted porphine; D, a
mixed amine/imine, the Curtis macrocycle; E, the related enamine/imine Jäger
macrocycle, and F, the tetracarboxylate-derivative DOTA macrocycle.
Nomenclature
IUPAC nomenclature has extensive rules to cover the naming of cyclic structures,
both as core structures, and as substituents appended to alicyclic structures.
[citation needed] The term macrocycle is used when a ring-containing compound has a
ring of 12 or more atoms.[5][6] The term polycyclic is used when more than one ring
appears in a single molecule. Naphthalene is formally a polycyclic compound, but is
more specifically named as a bicyclic compound. Several examples of macrocyclic and
polycyclic structures are given in the final gallery below.

The atoms that are part of the ring structure are called annular atoms.[9]

Isomerism
Stereochemistry
The closing of atoms into rings may lock particular atoms with distinct
substitution by functional groups such that the result is stereochemistry and
chirality of the compound, including some manifestations that are unique to rings
(e.g., configurational isomers).[4]
Conformational isomerism
To be supplied
Chair and boat conformers in cyclohexanes. Two conformers of cyclohexane, the chair
at left, and the boat at right (in German, respectively, Sessel and Wanne, the
latter meaning "bath").
To be supplied
cis-1,4-Dimethylcyclohexane, in chair form, minimising steric interactions between
the methyl groups in the directly opposing 1,4-positions of the cyclohexane ring.
General description. The structures are shown in line angle representation, though
in the image at left, the lines projecting from the cyclohexane are not terminal
methyl groups; rather, they indicate possible positions that might be occupied by
substituents (functional groups) attached to the ring. In the image at left, those
groups projecting upward and downward are termed axial substituents (a), and those
groups projecting around the conceptual equator are termed equatorial substituents
(e). Note, in general, the axial substituents are closer in space to one another
(allowing for repulsive interactions); moreover, in the boat form, axial
substituents in directly opposing positions (12 o'clock and 6 o'clock, termed
"1,4-") are very close in space, and therefore give rise to even greater repulsion.
These and other types of strain are used to explain the observation that the chair
conformation of cyclohexanes is the favored conformation.[4]
Depending on ring size, the three-dimensional shapes of particular cyclic
structures—typically rings of 5-atoms and larger—can vary and interconvert such
that conformational isomerism is displayed.[4] Indeed, the development of this
important chemical concept arose, historically, in reference to cyclic compounds.
For instance, cyclohexanes—six membered carbocycles with no double bonds, to which
various substituents might be attached, see image—display an equilibrium between
two conformations, the chair and the boat, as shown in the image.

The chair conformation is the favored configuration, because in this conformation,

the steric strain, eclipsing strain, and angle strain that are otherwise possible
are minimized.[4] Which of the possible chair conformations predominate in
cyclohexanes bearing one or more substituents depends on the substituents, and
where they are located on the ring; generally, "bulky" substituents—those groups
with large volumes, or groups that are otherwise repulsive in their
interactions[citation needed]—prefer to occupy an equatorial location.[4] An
example of interactions within a molecule that would lead to steric strain, leading
to a shift in equilibrium from boat to chair, is the interaction between the two
methyl groups in cis-1,4-dimethylcyclohexane. In this molecule, the two methyl
groups are in opposing positions of the ring (1,4-), and their cis stereochemistry
projects both of these groups toward the same side of the ring. Hence, if forced
into the higher energy boat form, these methyl groups are in steric contact, repel
one another, and drive the equilibrium toward the chair conformation.[4]

Aromaticity
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Cyclic compounds may or may not exhibit aromaticity; benzene is an example of an
aromatic cyclic compound, while cyclohexane is non-aromatic. In organic chemistry,
the term aromaticity is used to describe a cyclic (ring-shaped), planar (flat)
molecule that exhibits unusual stability as compared to other geometric or
connective arrangements of the same set of atoms. As a result of their stability,
it is very difficult to cause aromatic molecules to break apart and to react with
other substances. Organic compounds that are not aromatic are classified as
aliphatic compounds—they might be cyclic, but only aromatic rings have especial
stability (low reactivity).

Since one of the most commonly encountered aromatic systems of compounds in organic
chemistry is based on derivatives of the prototypical aromatic compound benzene (an
aromatic hydrocarbon common in petroleum and its distillates), the word “aromatic”
is occasionally used to refer informally to benzene derivatives, and this is how it
was first defined. Nevertheless, many non-benzene aromatic compounds exist. In
living organisms, for example, the most common aromatic rings are the double-ringed
bases in RNA and DNA. A functional group or other substituent that is aromatic is
called an aryl group.

The earliest use of the term “aromatic” was in an article by August Wilhelm Hofmann
in 1855. Hofmann used the term for a class of benzene compounds, many of which do
have odors (aromas), unlike pure saturated hydrocarbons. Today, there is no general
relationship between aromaticity as a chemical property and the olfactory
properties of such compounds (how they smell), although in 1855, before the
structure of benzene or organic compounds was understood, chemists like Hofmann
were beginning to understand that odiferous molecules from plants, such as
terpenes, had chemical properties we recognize today are similar to unsaturated
petroleum hydrocarbons like benzene.

In terms of the electronic nature of the molecule, aromaticity describes a

conjugated system often made of alternating single and double bonds in a ring. This
configuration allows for the electrons in the molecule's pi system to be
delocalized around the ring, increasing the molecule's stability. The molecule
cannot be represented by one structure, but rather a resonance hybrid of different
structures, such as with the two resonance structures of benzene. These molecules
cannot be found in either one of these representations, with the longer single
bonds in one location and the shorter double bond in another (See Theory below).
Rather, the molecule exhibits bond lengths in between those of single and double
bonds. This commonly seen model of aromatic rings, namely the idea that benzene was
formed from a six-membered carbon ring with alternating single and double bonds
(cyclohexatriene), was developed by August Kekulé (see History section below). The
model for benzene consists of two resonance forms, which corresponds to the double
and single bonds superimposing to produce six one-and-a-half bonds. Benzene is a
more stable molecule than would be expected without accounting for charge
delocalization.[citation needed]

Principal uses
Because of the unique shapes, reactivities, properties, and bioactivities that they
engender, cyclic compounds are the largest majority of all molecules involved in
the biochemistry, structure, and function of living organisms, and in the man-made
molecules (e.g., drugs, herbicides, etc.) through which man attempts to exert
control over nature and biological systems.

Synthetic reactions
Important general reactions for forming rings

Dieckmann ring-closing reaction

There are a variety of specialized reactions whose use is solely the formation of
rings, and these will be discussed below. In addition to those, there are a wide
variety of general organic reactions that historically have been crucial in the
development, first, of understanding the concepts of ring chemistry, and second, of
reliable procedures for preparing ring structures in high yield, and with defined
orientation of ring substituents (i.e., defined stereochemistry). These general
reactions include:
Acyloin condensation;
Anodic oxidations; and
the Dieckmann condensation as applied to ring formation.
Ring-closing reactions
In organic chemistry, a variety of synthetic procures are particularly useful in
closing carbocyclic and other rings; these are termed ring-closing reactions.
Examples include:

alkyne trimerisation;
the Bergman cyclization of an enediyne;
the Diels–Alder, between a conjugated diene and a substituted alkene, and other
cycloaddition reactions;
the Nazarov cyclization reaction, originally being the cyclization of a divinyl
ketone;
various radical cyclizations;
ring-closing metathesis reactions, which also can be used to accomplish a specific
type of polymerization;
the Ruzicka large ring synthesis, in which two carboxyl groups combine to form a
carbonyl group with loss of CO2 and H2O;
the Wenker synthesis converting a beta amino alcohol to an aziridine
other reactions, such as an amino group reacting with a hydroxy group, as in the
biosynthesis of solanine
Ring-opening reactions
A variety of further synthetic procedures are particularly useful in opening
carbocyclic and other rings, generally which contain a double bound or other
functional group "handle" to facilitate chemistry; these are termed ring-opening
reactions. Examples include:

ring opening metathesis, which can also be used to accomplish a specific type of
polymerization.
Ring expansion and ring contraction reactions
Main article: Ring expansion and ring contraction
Ring expansion and contraction reactions are common in organic synthesis, and are
frequently encountered in pericyclic reactions. Ring expansions and contractions
can involve the insertion of a functional group such as the case with Baeyer–
Villiger oxidation of cyclic ketones, rearrangements of cyclic carbocycles as seen
in intramolecular Diels-Alder reactions, or collapse or rearrangement of bicyclic
compounds as several examples.

Examples
Simple, mono-cyclic examples
The following are examples of simple and aromatic carbocycles, inorganic cyclic
compounds, and heterocycles:

Simple mono-cyclic compounds: Carbocyclic, inorganic, and heterocyclic (aromatic

and non-aromatic) examples.
Cycloheptane, a simple 7-membered carbocyclic compound, methylene hydrogens shown
(non-aromatic).
Cycloheptane, a simple 7-membered carbocyclic compound, methylene hydrogens shown
(non-aromatic).

Benzene, a 6-membered carbocyclic compound. methine hydrogens shown, and 6

electrons shown as delocalized through drawing of circle (aromatic).
Benzene, a 6-membered carbocyclic compound. methine hydrogens shown, and 6
electrons shown as delocalized through drawing of circle (aromatic).
Cyclo-octasulfur, an 8-membered inorganic cyclic compound (non-aromatic).
Cyclo-octasulfur, an 8-membered inorganic cyclic compound (non-aromatic).

Pentazole, a 5-membered inorganic cyclic compound (aromatic).

Pentazole, a 5-membered inorganic cyclic compound (aromatic).

Azetidine, a 4-membered nitrogen (aza) hetero-cyclic compound, methylene hydrogen

atoms implied, not shown (non-aromatic).
Azetidine, a 4-membered nitrogen (aza) hetero-cyclic compound, methylene hydrogen
atoms implied, not shown (non-aromatic).

Pyridine, a 6 membered heterocyclic compound, methine hydrogen atoms implied, not

shown, and delocalized π-electrons shown as discrete bonds (aromatic).
Pyridine, a 6 membered heterocyclic compound, methine hydrogen atoms implied, not
shown, and delocalized π-electrons shown as discrete bonds (aromatic).

Complex and polycyclic examples

The following are examples of cyclic compounds exhibiting more complex ring systems
and stereochemical features:

Complex cyclic compounds: Macrocyclic and polycyclic examples

Naphthalene, technically a polycyclic, more specifically a bicyclic compound, with
circles showing delocalization of π-electrons (aromatic).
Naphthalene, technically a polycyclic, more specifically a bicyclic compound, with
circles showing delocalization of π-electrons (aromatic).

Decalin (decahydronaphthalene), the fully saturated derivative of naphthalene,

showing the two stereochemistries possible for "fusing" the two rings together, and
how this impacts the shapes available to this bicyclic compound (non-aromatic).
Decalin (decahydronaphthalene), the fully saturated derivative of naphthalene,
showing the two stereochemistries possible for "fusing" the two rings together, and
how this impacts the shapes available to this bicyclic compound (non-aromatic).

Longifolene, a terpene natural product, and an example of a tricyclic molecule

(non-aromatic).
Longifolene, a terpene natural product, and an example of a tricyclic molecule
(non-aromatic).

Paclitaxel, a polycyclic natural product with a tricyclic core: with a

heterocyclic, 4-membered D ring, fused to further 6- and 8-membered carbocyclic
(A/C and B) rings (non-aromatic), and with three further pendant phenyl-rings on
its "tail", and attached to C-2 (abbrev. Ph, C6H5; aromatics).
Paclitaxel, a polycyclic natural product with a tricyclic core: with a
heterocyclic, 4-membered D ring, fused to further 6- and 8-membered carbocyclic
(A/C and B) rings (non-aromatic), and with three further pendant phenyl-rings on
its "tail", and attached to C-2 (abbrev. Ph, C6H5; aromatics).

A representative three-dimensional shape adopted by paclitaxel, as a result of its

unique cyclic structure.[10]
A representative three-dimensional shape adopted by paclitaxel, as a result of its
unique cyclic structure.[10]
Cholesterol, another terpene natural product, in particular, a steroid, a class of
tetracyclic molecules (non-aromatic).
Cholesterol, another terpene natural product, in particular, a steroid, a class of
tetracyclic molecules (non-aromatic).

Benzo[a]pyrene, a pentacyclic compound both natural and man-made, and delocalized

π-electrons shown as discrete bonds (aromatic).
Benzo[a]pyrene, a pentacyclic compound both natural and man-made, and delocalized
π-electrons shown as discrete bonds (aromatic).

Pagodane, a complex, highly symmetric, man-made polycyclic compound (non-aromatic).

Pagodane, a complex, highly symmetric, man-made polycyclic compound (non-aromatic).

Brevetoxin A, a natural product with ten rings, all fused, and all heterocyclic,
and a toxic component associated with the organisms responsible for red tides. The
R group at right refers to one of several possible four-carbon side chains (see
main Brevetoxin article; non-aromatic).
Brevetoxin A, a natural product with ten rings, all fused, and all heterocyclic,
and a toxic component associated with the organisms responsible for red tides. The
R group at right refers to one of several possible four-carbon side chains (see
main Brevetoxin article; non-aromatic).

See also
Effective molarity
Lactone
Open-chain compound
References
March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and
Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595[page
needed]
Halduc, I. (1961). "Classification of inorganic cyclic compounds". Journal of
Structural Chemistry. 2 (3): 350–8. doi:10.1007/BF01141802. S2CID 93804259.
Reymond, Jean-Louis (2015). "The Chemical Space Project". Accounts of Chemical
Research. 48 (3): 722–30. doi:10.1021/ar500432k. PMID 25687211.
William Reusch (2010). "Stereoisomers Part I" in Virtual Textbook of Organic
Chemistry. Michigan State University. Archived from the original on 10 March 2015.
Retrieved 7 April 2015.
Still, W.Clark; Galynker, Igor (1981). "Chemical consequences of conformation in
macrocyclic compounds". Tetrahedron. 37 (23): 3981–96. doi:10.1016/S0040-
4020(01)93273-9.
J. D. Dunitz (1968). J. D. Dunitz and J. A. Ibers (ed.). Perspectives in
Structural Chemistry. Vol. 2. New York: Wiley. pp. 1–70.
Eliel, E.L., Wilen, S.H. and Mander, L.S. (1994) Stereochemistry of Organic
Compounds, John Wiley and Sons, Inc., New York.[page needed]
Anet, F.A.L.; St. Jacques, M.; Henrichs, P.M.; Cheng, A.K.; Krane, J.; Wong, L.
(1974). "Conformational analysis of medium-ring ketones". Tetrahedron. 30 (12):
1629–37. doi:10.1016/S0040-4020(01)90685-4.
Morris, Christopher G.; Press, Academic (1992). Academic Press Dictionary of
Science and Technology. Gulf Professional Publishing. p. 120. ISBN 9780122004001.
Archived from the original on 2021-04-13. Retrieved 2020-09-14.
Löwe, J; Li, H; Downing, K.H; Nogales, E (2001). "Refined structure of αβ-tubulin
at 3.5 Å resolution". Journal of Molecular Biology. 313 (5): 1045–57.
doi:10.1006/jmbi.2001.5077. PMID 11700061. Archived from the original on 2021-01-
22. Retrieved 2020-09-14.
Further reading
Jürgen-Hinrich Fuhrhop & Gustav Penzlin, 1986, "Organic synthesis: concepts,
methods, starting materials," Weinheim, BW, DEU:VCH, ISBN 0895732467, see [1],
accessed 19 June 2015.
Michael B. Smith & Jerry March, 2007, "March's Advanced Organic Chemistry:
Reactions, Mechanisms, and Structure," 6th Ed., New York, NY, USA:Wiley & Sons,
ISBN 0470084944, see [2], accessed 19 June 2015.
Francis A. Carey & Richard J. Sundberg, 2006, "Title Advanced Organic Chemistry:
Part A: Structure and Mechanisms," 4th Edn., New York, NY, USA:Springer Science &
Business Media, ISBN 0306468565, see [3], accessed 19 June 2015.
Michael B. Smith, 2011, "Organic Chemistry: An Acid—Base Approach," Boca Raton, FL,
USA:CRC Press, ISBN 1420079212, see [4], accessed 19 June 2015. [May not be most
necessary material for this article, but significant content here is available
online.]
Jonathan Clayden, Nick Greeves & Stuart Warren, 2012, "Organic Chemistry," Oxford,
Oxon, GBR:Oxford University Press, ISBN 0199270295, see [5], accessed 19 June 2015.
László Kürti & Barbara Czakó, 2005, "Strategic Applications of Named Reactions in
Organic Synthesis: Background and Detailed Mechanisms, Amsterdam, NH, NLD:Elsevier
Academic Press, 2005ISBN 0124297854, see [6], accessed 19 June 2015.
External links
Polycyclic+Compounds at the U.S. National Library of Medicine Medical Subject
Headings (MeSH)
Macrocyclic+Compounds at the U.S. National Library of Medicine Medical Subject
Headings (MeSH)
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