A Newman projection is a drawing that helps visualize the 3-dimensional structure of a molecule. This projection most commonly sights down a carbon-carbon bond, making it a very useful way to visualize the stereochemistry of alkanes. A Newman projection visualizes the conformation of a

chemical bond A chemical bond is a lasting attraction between atoms or ions that enables the formation of molecules and crystals. The bond may result from the electrostatic force between oppositely charged ions as in ionic bonds, or through the sharing of ...

from front to back, with the front atom represented by the intersection of three lines (a dot) and the back atom as a circle. The front atom is called ''proximal'', while the back atom is called ''distal''. This type of representation clearly illustrates the specific

dihedral angle A dihedral angle is the angle between two intersecting planes or half-planes. In chemistry, it is the clockwise angle between half-planes through two sets of three atoms, having two atoms in common. In solid geometry, it is defined as the un ...

between the proximal and distal atoms. This projection is named after American chemist

Melvin Spencer Newman Melvin Spencer Newman (March 10, 1908 – May 30, 1993) was an American chemist, Ohio State University professor, best known for inventing the Newman projection. Newman was born in New York City in a Jewish family, the youngest of Mae (née P ...

, who introduced it in 1952 as a partial replacement for Fischer projections, which are unable to represent conformations and thus

conformers In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation). While any two arrangements of atoms in a molec ...

properly.Newman, MS. ''Record. Chem. Progr. (Kresge-Hooker Sci. Lib.) 1952,'' 13'', 111'' This diagram style is an alternative to a sawhorse projection, which views a carbon-carbon bond from an oblique angle, or a wedge-and-dash style, such as a

Natta projection In chemistry, the Natta projection (named for Italian chemist Giulio Natta) is a way to depict molecules with complete stereochemistry in two dimensions in a skeletal formula. In a hydrocarbon molecule with all carbon atoms making up the backb ...

. These other styles can indicate the bonding and

stereochemistry Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereois ...

, but not as much conformational detail. A Newman projection can also be used to study

cyclic molecule A cyclic compound (or ring compound) is a term for a chemical compound, compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a Ring (chemistry), ring. Rings may vary in size from three to many ...

s, such as the

chair conformation In organic chemistry, cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are ...

of cyclohexane: Because of the free rotation around single bonds, there are various conformations for a single molecule. Up to six unique conformations may be drawn for any given chemical bond. Each conformation is drawn by rotation of either the proximal or distal atom 60 degrees. Of these six conformations, three will be in a staggered conformation, while the other three will be in an eclipsed conformation. These six conformations can be represented in a relative energy diagram. Staggered-Eclipsed Newman Conformations

Newman projection relative energy diagram

A staggered projection appears to have the surrounding species equidistant from each other. This kind of conformation tends to experience both anti and gauche interactions. Anti interactions refer to the molecules (usually of the same type) sitting exactly opposite of each other at 180° on the Newman projection. Gauche interactions refer to molecules (also usually of the same type) being 60° from each other on a Newman projection. Anti interactions experience less steric strain than gauche interactions, but both experience less steric strain than the eclipsed conformation. An eclipsed projection appears to have the surrounding species almost on top of each other. In reality, these species are in line with each other, but are drawn slightly staggered to help format the projection onto paper. These types of conformations are generally higher in energy due to increased bond strain. However, this strain can be somewhat lower if a hydrogen is eclipsed over a larger species, as opposed to two large species eclipsed over each other.

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