AromaticityIn chemistry, aromaticity means the molecule has cyclic (ring-shaped) structures with pi bonds in resonance (those containing delocalized electrons). Aromatic rings give increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability.
Möbius aromaticityIn organic chemistry, Möbius aromaticity is a special type of aromaticity believed to exist in a number of organic molecules. In terms of molecular orbital theory these compounds have in common a monocyclic array of molecular orbitals in which there is an odd number of out-of-phase overlaps, the opposite pattern compared to the aromatic character to Hückel systems. The nodal plane of the orbitals, viewed as a ribbon, is a Möbius strip, rather than a cylinder, hence the name.
Hückel's ruleIn organic chemistry, Hückel's rule predicts that a planar ring molecule will have aromatic properties if it has 4n + 2 π electrons, where n is a non-negative integer. The quantum mechanical basis for its formulation was first worked out by physical chemist Erich Hückel in 1931. The succinct expression as the 4n + 2 rule has been attributed to W. v. E. Doering (1951), although several authors were using this form at around the same time.
Conjugated systemIn 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.
Resonance (chemistry)In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or forms, also variously known as resonance structures or canonical structures) into a resonance hybrid (or hybrid structure) in valence bond theory. It has particular value for analyzing delocalized electrons where the bonding cannot be expressed by one single Lewis structure.
AntiaromaticityAntiaromaticity is a chemical property of a cyclic molecule with a π electron system that has higher energy, i.e., it is less stable due to the presence of 4n delocalised (π or lone pair) electrons in it, as opposed to aromaticity. Unlike aromatic compounds, which follow Hückel's rule ([4n+2] π electrons) and are highly stable, antiaromatic compounds are highly unstable and highly reactive. To avoid the instability of antiaromaticity, molecules may change shape, becoming non-planar and therefore breaking some of the π interactions.
Alicyclic compoundIn organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. The simplest alicyclic compounds are the monocyclic cycloalkanes: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and so on. Bicyclic alkanes include bicycloundecane, decalin, and housane. Polycyclic alkanes include cubane, basketane, and tetrahedrane.
Delocalized electronIn chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond. The term delocalization is general and can have slightly different meanings in different fields: In organic chemistry, it refers to resonance in conjugated systems and aromatic compounds. In solid-state physics, it refers to free electrons that facilitate electrical conduction. In quantum chemistry, it refers to molecular orbital electrons that have extended over several adjacent atoms.
Double bondIn chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O).
Stacking (chemistry)In chemistry, pi stacking (also called π–π stacking) refers to the presumptive attractive, noncovalent pi interactions (orbital overlap) between the pi bonds of aromatic rings. However this is a misleading description of the phenomena since direct stacking of aromatic rings (the "sandwich interaction") is electrostatically repulsive.
