In molecular geometry, bond length or bond distance is the distance between two bonded atoms in a molecule. Geometry of the water molecule Molecular geometry or molecular structure is the three dimensional arrangement of the atoms that constitute a molecule, inferred from the spectroscopic studies of the compound. ... A chemical bond is the physical phenomenon of chemical substances being held together by attraction of atoms to each other through sharing, as well as exchanging, of electrons or electrostatic forces. ... Properties For other uses, see Atom (disambiguation). ... In chemistry, a molecule is an aggregate of at least two atoms in a definite arrangement held together by special forces. ...

Explanation

Bond length is directly related to bond order, when more electrons participate in bond formation the bond will get shorter. Bond length is also directly related to bond strength and the bond dissociation energy as a stronger bond is also a shorter bond. In a bond between two identical atoms half the bond distance is equal to the covalent radius. Bond lengths are measured in molecules by means of x-ray diffraction. A set of two atoms sharing a bond is unique going from one molecule to the next. For example the carbon to hydrogen bond in methane is different from that in methyl chloride. It is however possible to make generalizations when the general structure is the same. Bond order is the number of bonds between a pair of atoms. ... Properties The electron is a lightweight fundamental subatomic particle that carries a negative electric charge. ... In chemistry, bond strength is measured between two atoms joined in a chemical bond. ... In chemistry, bond dissociation energy, D0, is one measure of the bond strength in a chemical bond. ... Covalent radius in chemistry corresponds to half of the distance between two identical atomic nuclei, bound by a covalent bond. ... X-ray crystallography is a technique in crystallography in which the pattern produced by the diffraction of x-rays through the closely spaced lattice of atoms in a crystal is recorded and then analyzed to reveal the nature of that lattice. ... The simplest hydrocarbon, methane, is a gas (at standard temperature and pressure (STP)) with a chemical formula of CH4. ... Chloromethane or Methyl chloride is a chemical compound once widely used as a refrigerant. ...

Bond lengths of carbon with other elements

A table with experimental single bonds for carbon to other elements ^[1] is given below. Bond lengths are given in picometers. By approximation the bond distance between two different atoms is the sum of the individual covalent radii (these are given in the chemical element articles for each element). As a general trend, bond distances decrease across the row in the periodic table and increase down a group. This trend is identical to that of the atomic radius. Covalently bonded hydrogen and carbon in a molecule of methane. ... Picometre (American spelling: picometer) is an SI measure of length that is equal to 10−12 of a metre. ... Covalent radius in chemistry corresponds to half of the distance between two identical atomic nuclei, bound by a covalent bond. ... The periodic table of the chemical elements A chemical element, often called simply an element, is a substance that cannot be decomposed or transformed into other chemical substances by ordinary chemical processes. ... The periodic table of the chemical elements is a tabular method of displaying the chemical elements, first devised in 1869 by the Russian chemist Dmitri Mendeleev. ... The atomic radius is the distance from the atomic nucleus to the outmost stable electron orbital in an atom that is at equilibrium. ...

General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... The alkali metals are a chemical series. ... General Name, Symbol, Number beryllium, Be, 4 Chemical series alkaline earth metals Group, Period, Block 2, 2, s Appearance white-gray metallic Atomic mass 9. ... The alkaline earth metals are the series of elements in Group 2 (IUPAC style) of the periodic table: beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba) and radium (Ra) (not always considered due to its radioactivity and very short half-life). ... General Name, Symbol, Number magnesium, Mg, 12 Chemical series alkaline earth metals Group, Period, Block 2, 3, s Appearance silvery white Atomic mass 24. ... The alkaline earth metals are the series of elements in Group 2 (IUPAC style) of the periodic table: beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba) and radium (Ra) (not always considered due to its radioactivity and very short half-life). ... It has been suggested that Boriding be merged into this article or section. ... The Boron group is the series of elements in group 13 (IUPAC style) in the periodic table. ... Aluminum is a soft and lightweight metal with a dull silvery appearance, due to a thin layer of oxidation that forms quickly when it is exposed to air. ... The Boron group is the series of elements in group 13 (IUPAC style) in the periodic table. ... General Name, Symbol, Number indium, In, 49 Chemical series poor metals Group, Period, Block 13, 5, p Appearance silvery lustrous gray Atomic mass 114. ... The Boron group is the series of elements in group 13 (IUPAC style) in the periodic table. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... The carbon group is group 14 (IUPAC style) in the periodic table. ... General Name, Symbol, Number silicon, Si, 14 Chemical series metalloids Group, Period, Block 14, 3, p Appearance dark gray, bluish tinge Atomic mass 28. ... The carbon group is group 14 (IUPAC style) in the periodic table. ... General Name, Symbol, Number tin, Sn, 50 Chemical series poor metals Group, Period, Block 14, 5, p Appearance silvery lustrous gray Atomic mass 118. ... The carbon group is group 14 (IUPAC style) in the periodic table. ... General Name, Symbol, Number lead, Pb, 82 Chemical series poor metals Group, Period, Block 14, 6, p Appearance bluish white Atomic mass 207. ... The carbon group is group 14 (IUPAC style) in the periodic table. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... The Nitrogen group elements (a. ... This article is about the chemical element. ... The Nitrogen group elements (a. ... General Name, Symbol, Number arsenic, As, 33 Chemical series metalloids Group, Period, Block 15, 4, p Appearance metallic gray Atomic mass 74. ... The Nitrogen group elements (a. ... General Name, Symbol, Number antimony, Sb, 51 Chemical series metalloids Group, Period, Block 15, 5, p Appearance silvery lustrous grey Atomic mass 121. ... The Nitrogen group elements (a. ... General Name, Symbol, Number bismuth, Bi, 83 Chemical series poor metals Group, Period, Block 15, 6, p Appearance lustrous reddish white Atomic mass 208. ... The Nitrogen group elements (a. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... General Name, Symbol, Number chromium, Cr, 24 Chemical series transition metals Group, Period, Block 6, 4, d Appearance silvery metallic Atomic mass 51. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... SE redirects here. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... General Name, Symbol, Number tellurium, Te, 52 Chemical series metalloids Group, Period, Block 16, 5, p Appearance silvery lustrous gray Atomic mass 127. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... General Name, Symbol, Number molybdenum, Mo, 42 Chemical series transition metals Group, Period, Block 6, 5, d Appearance gray metallic Atomic mass 95. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... General Name, Symbol, Number tungsten, W, 74 Chemical series transition metals Group, Period, Block 6, 6, d Appearance grayish white, lustrous Atomic mass 183. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... The halogens The halogens are a chemical series. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... The halogens The halogens are a chemical series. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... The halogens The halogens are a chemical series. ... General Name, Symbol, Number iodine, I, 53 Chemical series halogens Group, Period, Block 17, 5, p Appearance violet-dark gray, lustrous Atomic mass 126. ... The halogens The halogens are a chemical series. ... Picometre (American spelling: picometer) is an SI measure of length that is equal to 10−12 of a metre. ...

Bond lengths in organic compounds

The actual bond length between two atoms in a molecule depends on such factors as the orbital hybridisation and the electronic and steric nature of the substituents. The carbon carbon bond length in diamond is 154 pm which is also the largest bond length that exists for ordinary carbon covalent bonds. four sp³ orbitals three sp² orbitals In chemistry, hybridisation or hybridization (see spelling differences) is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ...

Unusually long bond lengths do exists. In one tricyclobutabenzene a bond length of 160 pm is reported. The current record holder is another cyclobutabenzene with length 174 pm based on X-ray crystallography ^[3]. In this type of compounds the cyclobutane ring would force 90° angles on the carbon atoms connected to the benzene ring where they ordinarily have angles of 120°. Tricyclobutabenzene is an aromatic hydrocarbon consisting of a benzene core with three cyclobutane rings fused onto it. ... X-ray crystallography is a technique in crystallography in which the pattern produced by the diffraction of X-rays through the closely spaced lattice of atoms in a crystal is recorded and then analyzed to reveal the nature of that lattice. ...

The existence of a very long C-C bond length of up to 290 pm is claimed in a dimer of two tetracyanoethylenedianions although this concerns a 2-electron-4-center bond ^[4]. This type of bonding has also been observed in dimers of neutral phenalene dimers. The bond lengths of these so-called pancake bonds ^[5] are up to 305 pm. Image File history File links Unusualbondlength. ... Tetracyanoethylene (TCNE) is an organic compound consisting of ethylene with the four hydrogen atom replaced with cyano groups. ...

Shorter than average carbon carbon bonds distances are also possible, alkenes and alkynes have bond lengths of respectively 133 and 120 pm due to increased s-character of the sigma bond.In benzene all bonds have the same length: 139 pm. In carbon carbon single bonds increased s-character is also notable in the central bond of diacetylene (137 pm) and that of a certain tetrahedrane dimer (144 pm). An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ... Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ... In chemistry, hybridisation is the mixing of atomic orbitals to form new orbitals suitable for bonding. ... Electron atomic and molecular orbitals, showing among others the sigma bond of two s-orbitals and a sigma bond of two p-orbitals In chemistry, sigma bonds (σ-bonds) are bonds where there is no nodal plane containing the line segment between the two bonded species. ... Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... Diacetylene is an unsaturated hydrocarbon with chemical formula HCCCCH. Categories: Stub ... Tetrahedrane is a hypothetical hydrocarbon with chemical formula C4H4 and a tetrahedral structure. ...

In propionitrile the cyano group withdraws electrons also resulting in a reduced bond length (144 pm). Squeezing a CC bond is also possible by application of strain. An unusual organic compound exists called In-Methylcyclophane with a very short bond distance of 147 pm for the methyl group being squeezed between a trypticene and a phenyl group. In an in silico experiment a bond distance of 136 pm is estimated for neopentane locked up in fullerene ^[6]. The smallest theoretical CC single bond obtained in this study is 132 pm for a hypothetical adamantane like molecule. Propionitrile, or ethyl cyanide, has formula C2H5CN. It melts at -93 °C and boils at 97 °C. Template:Organic-chem-stub Categories: Nitriles ... A cyanide is any chemical compound that contains the cyano group C≡N, with the carbon atom triple-bonded to the nitrogen atom. ... In chemistry van der Waals strain is strain resulting from van der Waals repulsion when two substituents in a molecule approach each other with a distance less than the sum of their van der Waals radii. ... In-Methylcyclophanes are organic compounds and members of a larger family of cyclophanes. ... Triptycenes are a class of aromatic hydrocarbons. ... in silico is an expression used to mean performed on computer or via computer simulation. ... Pentane also known as amyl hydride or skellysolve is an alkane hydrocarbon with the chemical formula CH3(CH2)3CH3. ... The fullerenes are a recently-discovered family of carbon allotropes named after Buckminster Fuller. ... Adamantane (Tricyclo[3. ...

In the same study it is estimated that for ethane it takes 2.8 kJ/mol to stretch the CC bond by 5 pm from its equilibrium value and only 3.5 kJ/mol to squeeze it by the same amount. on the other hand, stretching and squeezing by 15 pm requires 21.9 and 37.7 kJ/mol. Ethane is a chemical compound with chemical formula C2H6. ... The joule (symbol: J) is the SI unit of energy, or work with base units of kg·m²/s² (N·m). ... The mole and its simple conversions into different units of measurements. ...

Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ... Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ...

See also

• Chemical bond
• Molecule

A chemical bond is the physical phenomenon of chemical substances being held together by attraction of atoms to each other through sharing, as well as exchanging, of electrons or electrostatic forces. ... In chemistry, a molecule is an aggregate of at least two atoms in a definite arrangement held together by special forces. ...

External links

• Utah Chemists Find Longest Carbon-Carbon Bond Press release

References

1. ↑  Handbook of Chemistry & Physics 65th Edition CRC Press ISBN 0-8493-0465-2
2. ↑  Naphthocyclobutenes and Benzodicyclobutadienes: Synthesis in the Solid State and Anomalies in the Bond Lengths Fumio Toda European Journal of Organic Chemistry Volume 2000, Issue 8, Date: April 2000, Pages: 1377-1386 Abstract
3. ↑  Exceptionally Long (2.9 Å) C-C Bonds between [TCNE]- Ions: Two-Electron, Four-Center *-* C-C Bonding in -[TCNE]22- Angewandte Chemie International Edition Volume 40, Issue 13, Date: July 2, 2001, Pages: 2540-2545 Juan J. Novoa, Pilar Lafuente, Rico E. Del Sesto, Joel S. Miller Abstract
4. ↑  Stable (Long-Bonded) Dimers via the Quantitative Self-Association of Different Cationic, Anionic, and Uncharged -Radicals: Structures, Energetics, and Optical Transitions Jian-Ming Lü, Sergiy V. Rosokha, and Jay K. Kochi J. Am. Chem. Soc.; 2003; 125(40) pp 12161 Abstract
5. ↑  Aromaticity on the Pancake-Bonded Dimer of Neutral Phenalenyl Radical as Studied by MS and NMR Spectroscopies and NICS Analysis Shuichi Suzuki, Yasushi Morita, Kozo Fukui, Kazunobu Sato, Daisuke Shiomi, Takeji Takui, and Kazuhiro Nakasuji J. Am. Chem. Soc.; 2006; 128(8) pp 2530 Abstract
6. ↑  Squeezing CC Bonds Deborah R. Huntley, Georgios Markopoulos, Patrick M. Donovan, Lawrence T. Scott, Roald Hoffmann Angewandte Chemie International Edition Volume 44, Issue 46 , Pages 7549 - 7553 2005
7. ↑  Fox, MA and JK Whitesell. Organische Chemie. 1994. Spektrum

Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ... The Journal of the American Chemical Society (usually abbreviated as , or JACS), is a peer-reviewed scientific journal, published since 1879 by the American Chemical Society. ... The Journal of the American Chemical Society (usually abbreviated as , or JACS), is a peer-reviewed scientific journal, published since 1879 by the American Chemical Society. ... Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ...

External links

• Bond length tutorial