Ladderane
Encyclopedia
A ladderane is an organic molecule
containing two or more fused rings of cyclobutane
. The name is a portmanteau because the serial cyclobutane rings look like a ladder and are singly bonded like alkane
s. The chemical formula for a ladderane with n rings is C
2n+2H
2n+6. The geometry of ladderanes is highly strained because ligands to the carbon atoms cannot extend to their ideal angles. However, examples of ladderanes have been found in living organisms. An example is pentacycloanammoxic acid which is composed of 5 fused cyclobutane units. It is found in bacteria performing the anammox
process where it forms part of a tight and very dense membrane believed to prevent the organism from losing the intermediate hydrazine
which is involved in the production of nitrogen and water from nitrite
ions and ammonia
.
Ladderanes can be formed by the reduction of a carbon-carbon double bond into a single bond, concomitant with the creation of a new carbon-carbon bond to close the ring.
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...
containing two or more fused rings of cyclobutane
Cyclobutane
Cyclobutane is an organic compound with the formula 4. Cyclobutane is a colourless gas and commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes...
. The name is a portmanteau because the serial cyclobutane rings look like a ladder and are singly bonded like alkane
Alkane
Alkanes are chemical compounds that consist only of hydrogen and carbon atoms and are bonded exclusively by single bonds without any cycles...
s. The chemical formula for a ladderane with n rings is C
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
2n+2H
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
2n+6. The geometry of ladderanes is highly strained because ligands to the carbon atoms cannot extend to their ideal angles. However, examples of ladderanes have been found in living organisms. An example is pentacycloanammoxic acid which is composed of 5 fused cyclobutane units. It is found in bacteria performing the anammox
Anammox
Anammox, an abbreviation for ANaerobic AMMonium OXidation, is a globally important microbial process of the nitrogen cycle . The bacteria mediating this process were identified in 1991, and at the time were a great surprise for the scientific community...
process where it forms part of a tight and very dense membrane believed to prevent the organism from losing the intermediate hydrazine
Hydrazine
Hydrazine is an inorganic compound with the formula N2H4. It is a colourless flammable liquid with an ammonia-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually...
which is involved in the production of nitrogen and water from nitrite
Nitrite
The nitrite ion has the chemical formula NO2−. The anion is symmetric with equal N-O bond lengths and a O-N-O bond angle of ca. 120°. On protonation the unstable weak acid nitrous acid is produced. Nitrite can be oxidised or reduced, with product somewhat dependent on the oxidizing/reducing agent...
ions and ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
.
Ladderanes can be formed by the reduction of a carbon-carbon double bond into a single bond, concomitant with the creation of a new carbon-carbon bond to close the ring.