Carbon dioxide bond lengths

Carbon dioxide has a linear structure. The simple double-bonded formula, however, does not fully explain the structure since the measured carbon-oxygen bond lengths are equal but intermediate between those expected for a double and a triple bond. A more accurate representation is, therefore, obtained by considering carbon dioxide as a resonance hybrid of the three structures given below ... 

Carbon dioxide or CO2. Carbon dioxide is a linear molecule, 0=C=0 with a mean carbon-oxygen bond length of 0.116 nm. See Carbon Dioxide... 

The enthalpy of formation of carbon dioxide is —394 kJ mole. Its heat of sublimation at —78.48°C (1 atm pressure) is 25 kJ mole . The molecule is linear, with carbon-oxygen bond length 115.9 pm. 

A unique characteristic feature of the cyclic three-membered ring sulfones and sulfoxides is the dramatic increase in the length of the carbon-carbon single bonds and the carbon-carbon double bonds in the series of thiirane-thiirane oxide-thiirane dioxide (20a -> 16a -> 17a), and thiirene-thiirene oxide-thiirene dioxide (21 -> 18a -> 19b). 

Conjugation of the 7t-electrons of the carbon-carbon double bond with the LUMO sulfur 3d-orbitals would be expected to stabilize the Hiickel 4n -I- 2 (n = 0) array of n-electrons in the thiirene dioxide system. No wonder, therefore, that the successful synthesis of the first member in this series (e.g. 19b) has initiated and stimulated several studies , the main objective of which was to determine whether or not thiirene dioxides should be considered to be aromatic (or pseudo-aromatic ) and/or to what extent conjugation effects, which require some sort of n-d bonding in the conjugatively unsaturated sulfones, are operative within these systems. The fact that the sulfur-oxygen bond lengths in thiirene dioxides were found to be similar to those of other 802-containing compounds, does not corroborate a Hiickel-type jr-delocalization... 

Carbon dioxide is a symmetrical, linear triatomic molecule (0 = C=0) with a zero dipole moment. The carbon-to-hydrogen bond distances are about 1.16A, which is about 0.06A shorter than typical carbonyl double bonds. This shorter bond length was interpreted by Pauling to indicate that greater resonance stabilization occurs with CO2 than with aldehydes, ketones, or amides. When combined with water, carbonic acid (H2CO3) forms, and depending on the pH of the solution, carbonic acid loses one or two protons to form bicarbonate and carbonate, respectively. The various thermodynamic parameters of these reactions are shown in Table I. 

Bond length/bond enthalpy. Note that 1 A equals 0.1 nm. 6 Bond lengths are given for bonds in which none of the partner atoms is involved in a double or triple bond. In such cases bond lengths are somewhat shorter.c In carbon disulfide.d In aldehydes. e In ketones, f In carbon dioxide. 

In som6 later discussion (such as that of carbon dioxide, Sec. 8-1) we shall use —0.020 A as the correction to bond length corresponding to resonance between two equivalent structures. 

A mononuclear tantalum-benzyne complex (121) has been prepared by thermolysis of 120 [Eq. (20)].14 An X-ray crystal structure was reported for 121. Bond lengths for the benzyne unit are given in Table III. Complex 121 exhibits a rich insertion chemistry similar to that of Ti, Zr, and Ru benzyne complexes. Insertion reactions of 121 with ethylene, 2-butyne, acetonitrile, and carbon dioxide give 122, 123, 124, and 125, respectively (Scheme 15). Diphenylacetylene does not couple with 121, presumably because of steric constraints. Reagents with acidic protons such as methanol or terminal alkynes cleave the Ta—C bond to give butyl isocyanide and carbon monoxide, but... 

The geometry of this molecule was obtained assuming C v S5nnmetry. The calculated C—O bond lengths (1.374 A) are considerably shorter than in dioxirane (1.424 A) though not as short as in hydroxymethylidene (1.331 A) reflecting the extensive delocalization of the oxygen lone pairs into the vacant 2p orbital at C. The carbon 2p electron populations in dioxiranylidene and hydroxymethylidene are 0.225 and 0.227 respectively (4-31G). Dioxiranylidene is an isomer of carbon dioxide and is calculated to be 161.3 kcal/mol less stable than the latter (4-31G).5D If this is correct, dioxiranylidene would be unstable relative to CO + O. 

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